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Shanghai Upbio Tech Co.,Ltd

1.No Less 8 years exporting experience. Clients can 100% received goods 2.Lower Price with higher quality 3,Free sample 4,We are sincerely responsible for the "product quality" and "After Service" Upbio is Specialized

Spiro[11-oxabicyclo[8.1.0]undec-6-ene-2,2'-oxiran]-3-one,8-methylene-5-(1-methylethyl)-, (1R,2R,5S,6E,10R)- 61228-92-0

Cas:61228-92-0

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

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Qingdao Beluga Import and Export Co., LTD

PERIPLANONEB CAS:61228-92-0 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing in high quality organic intermediate

PERIPLANONEB CAS:61228-92-0

Cas:61228-92-0

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

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Shandong Hanjiang Chemical Co., Ltd.

Hello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai

Spiro[11-oxabicyclo[8.1.0]undec-6-ene-2,2'-oxiran]-3-one,8-methylene-5-(1-methylethyl)-, (1R,2R,5S,6E,10R)-

Cas:61228-92-0

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

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Henan Wentao Chemical Product Co., Ltd.

Henan Wentao Chemical Product Co.,Ltd is Located in Zhengzhou High-tech Development Zone with import and export license, We passed ISO 9001:2008 as well, Henan Wentao has developed more than 1000 compounds, which are widely used in the fields of prod

Spiro[11-oxabicyclo[8.1.0]undec-6-ene-2,2'-oxiran]-3-one,8-methylene-5-(1-methylethyl)-, (1R,2R,5S,6E,10R)-

Cas:61228-92-0

Min.Order:0

Negotiable

Type:Lab/Research institutions

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Zibo Hangyu Biotechnology Development Co., Ltd

Zibo Hangyu Biotechnology Development Co., Ltd is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemi

Spiro[11-oxabicyclo[8.1.0]undec-6-ene-2,2'-oxiran]-3-one,8-methylene-5-(1-methylethyl)-, (1R,2R,5S,6E,10R)-

Cas:61228-92-0

Min.Order:10 Gram

FOB Price: $100.0

Type:Lab/Research institutions

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Hangzhou Dingyan Chem Co., Ltd

R & D enterprises have their own stock in stock Package:1kg Application:pharmaceutical intermediates

Spiro[11-oxabicyclo[8.1.0]undec-6-ene-2,2'-oxiran]-3-one,8-methylene-5-(1-methylethyl)-, (1R,2R,5S,6E,10R)-

Cas:61228-92-0

Min.Order:0

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Type:Manufacturers

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Henan Tianfu Chemical Co., Ltd.

1.Our services：A.Supply sampleB.The packing also can be according the customers` requirmentC.Any inquiries will be replied within 24 hoursD.we provide Commerical Invoice, Packing List, Bill of loading, COA , Health certificate and Origin certificate.

Spiro[11-oxabicyclo[8.1.0]undec-6-ene-2,2'-oxiran]-3-one,8-methylene-5-(1-methylethyl)-, (1R,2R,5S,6E,10R)-

Cas:61228-92-0

Min.Order:0

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Type:Lab/Research institutions

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Antimex Chemical Limied

Ansciep Chemical is a professional enterprise manufacturing and distributing fine chemicals and speciality chemicals. We have been dedicated to heterocycle compounds and phenyl rings for tens of years. This is our mature product for export. Our quali

Spiro[11-oxabicyclo[8.1.0]undec-6-ene-2,2'-oxiran]-3-one,8-methylene-5-(1-methylethyl)-, (1R,2R,5S,6E,10R)-

Cas:61228-92-0

Min.Order:0

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Henan Kanbei Chemical Co.,LTD

factory?direct?saleAppearance:White powder Storage:Sealed and preserved Package:200/Kilograms Application:healing drugs Transportation:By sea Port:Shanghai/tianjin

PERIPLANONEB

Cas:61228-92-0

Min.Order:0

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ZHEJIANG JIUZHOU CHEM CO.,LTD

factory?direct?saleAppearance:White powder Storage:Sealed and preserved Package:200/Kilograms Application:healing drugs Transportation:By sea Port:Shanghai/tianjin

PERIPLANONEB

Cas:61228-92-0

Min.Order:0

Negotiable

Type:Trading Company

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Shanghai united Scientific Co.,Ltd.

United Scientific Company Located in Shanghai of China , is a competitive player in the global specialty and fine chemical market. Fenghua has both the expertise and flexibility to produce a wide range of chemicals. Focusing on developing the innovat

Spiro[11-oxabicyclo[8.1.0]undec-6-ene-2,2'-oxiran]-3-one,8-methylene-5-(1-methylethyl)-, (1R,2R,5S,6E,10R)-

Cas:61228-92-0

Min.Order:0

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Type:Lab/Research institutions

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Chungking Joyinchem Co., Ltd.

Joyinchem have been committed to chemical supply for several years and have built good cooperation records with multinational chemical corporations and importers from all over the world. Our services include:-Spot goods-Contract manufacturing-Custom

Spiro[11-oxabicyclo[8.1.0]undec-6-ene-2,2'-oxiran]-3-one,8-methylene-5-(1-methylethyl)-, (1R,2R,5S,6E,10R)-

Cas:61228-92-0

Min.Order:0

Negotiable

Type:Lab/Research institutions

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Nanjing Raymon Biotech Co., Ltd.

Spiro[11-oxabicyclo[8.1.0]undec-6-ene-2,2'-oxiran]-3-one,8-methylene-5-(1-methylethyl)-, (1R,2R,5S,6E,10R)-Appearance:Off white to slight yellow solid Storage:Store in dry and cool condition Package:25kg or according to cutomer's demand Application:C

Spiro[11-oxabicyclo[8.1.0]undec-6-ene-2,2'-oxiran]-3-one,8-methylene-5-(1-methylethyl)-, (1R,2R,5S,6E,10R)-

Cas:61228-92-0

Min.Order:0

Negotiable

Type:Trading Company

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Hebei Ruishun Trade Co.,Ltd

Supply top quality products with a reasonable price Application:api

61228-92-0

Cas:61228-92-0

Min.Order:0

Negotiable

Type:Trading Company

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Chemical Co.Ltd

Spiro[11-oxabicyclo[8.1.0]undec-6-ene-2,2'-oxiran]-3-one,8-methylene-5-(1-methylethyl)-, (1R,2R,5S,6E,10R)-Appearance:Off white to slight yellow solid Storage:Stored in shaded, cool and dry places Package:1L 5L 10L 25L bottle Application:pharma inter

Spiro[11-oxabicyclo[8.1.0]undec-6-ene-2,2'-oxiran]-3-one,8-methylene-5-(1-methylethyl)-, (1R,2R,5S,6E,10R)-

Cas:61228-92-0

Min.Order:0

Negotiable

Type:Trading Company

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View More

Synthetic route

(1S,3S,4E,8R,9R,10S)-8,9-epoxy-10,10-epoxymethano-3-isopropyl-6-methylene-4-cyclodecen-1-ol
70800-65-6, 70831-70-8, 70831-72-0, 70831-75-3, 84236-08-8

(1S,3S,4E,8R,9R,10S)-8,9-epoxy-10,10-epoxymethano-3-isopropyl-6-methylene-4-cyclodecen-1-ol

(3S,8R,9R,10S)-(-)-periplanone-B
61228-92-0

(3S,8R,9R,10S)-(-)-periplanone-B

Conditions
ConditionsYield
With dipyridinium dichromate In N,N-dimethyl-formamide for 2h; Ambient temperature;92%
With dipyridinium dichromate In N,N-dimethyl-formamide92%
With 3 A molecular sieve; pyridinium chlorochromate In dichloromethane for 1h; Ambient temperature;88%
methylenedimethyl sulfurane
6814-64-8, 40651-06-7

methylenedimethyl sulfurane

(E)-(1R,5S,10R)-5-Isopropyl-8-methylene-11-oxa-bicyclo[8.1.0]undec-6-ene-2,3-dione
105930-41-4

(E)-(1R,5S,10R)-5-Isopropyl-8-methylene-11-oxa-bicyclo[8.1.0]undec-6-ene-2,3-dione

(3S,8R,9R,10S)-(-)-periplanone-B
61228-92-0

(3S,8R,9R,10S)-(-)-periplanone-B

Conditions
ConditionsYield
In tetrahydrofuran; dimethyl sulfoxide at 0℃; for 0.166667h;
(4S,5E,9R,10R)-9,10-epoxy-7-methylene-4-(1-methylethyl)-5-cyclodecene-1-one
105930-39-0

(4S,5E,9R,10R)-9,10-epoxy-7-methylene-4-(1-methylethyl)-5-cyclodecene-1-one

(3S,8R,9R,10S)-(-)-periplanone-B
61228-92-0

(3S,8R,9R,10S)-(-)-periplanone-B

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 86 percent / LiN(TMS)2, MoO5*HMPA*Py / tetrahydrofuran
2: imidazole / dimethylformamide
3: n-BuLi / tetrahydrofuran
4: n-Bu4NF / tetrahydrofuran
5: 92 percent / PDC / dimethylformamide
View Scheme
Multi-step reaction with 5 steps
1: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
2: dimethylformamide / 16 h / 40 °C
3: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
4: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
5: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 3 steps
1: 1) LiN(TMS)2, 2) MoO5*HMPA*Py / 1) THF, 30 min, 2) -70 degC, 5 min
2: PCC / CH2Cl2 / 5 h / Ambient temperature; Molecular sieves 3A
3: tetrahydrofuran; dimethylsulfoxide / 0.17 h / 0 °C
View Scheme
Multi-step reaction with 5 steps
1: 1) LiN(TMS)2, 2) MoO5*HMPA*py / 1) -78 deg C, 1 h, THF, 2) -20 deg C, 25 min
2: imidazole / dimethylformamide / 17 h / Ambient temperature
3: 1) n-BuLi / 1) THF, hexane, 10 min, 2a) THF, -15 deg C, 10 min, 2b) 20 min, 0 deg C
4: (n-Bu)4NF / tetrahydrofuran / 0.17 h / Ambient temperature
5: 92 percent / PDC / dimethylformamide / 2 h / Ambient temperature
View Scheme
(2S,4S,5E,9R,10R)-2-t-butyldimethylsilyloxy-9,10-epoxy-7-methylene-4-(1-methylethyl)-5-cyclodecene-1-one
113666-35-6

(2S,4S,5E,9R,10R)-2-t-butyldimethylsilyloxy-9,10-epoxy-7-methylene-4-(1-methylethyl)-5-cyclodecene-1-one

(3S,8R,9R,10S)-(-)-periplanone-B
61228-92-0

(3S,8R,9R,10S)-(-)-periplanone-B

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: n-BuLi / tetrahydrofuran
2: n-Bu4NF / tetrahydrofuran
3: 92 percent / PDC / dimethylformamide
View Scheme
Multi-step reaction with 3 steps
1: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
2: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
3: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 3 steps
1: 1) n-BuLi / 1) THF, hexane, 10 min, 2a) THF, -15 deg C, 10 min, 2b) 20 min, 0 deg C
2: (n-Bu)4NF / tetrahydrofuran / 0.17 h / Ambient temperature
3: 92 percent / PDC / dimethylformamide / 2 h / Ambient temperature
View Scheme
(1S,3S,4E,8R,9R,10R)-1-t-butyldimethylsilyloxy-8,9-epoxy-6-methylene-10,10-methylenoxy-3-(1-methylethyl)-4-cyclodecene
70552-76-0, 70614-01-6, 113666-36-7

(1S,3S,4E,8R,9R,10R)-1-t-butyldimethylsilyloxy-8,9-epoxy-6-methylene-10,10-methylenoxy-3-(1-methylethyl)-4-cyclodecene

(3S,8R,9R,10S)-(-)-periplanone-B
61228-92-0

(3S,8R,9R,10S)-(-)-periplanone-B

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: n-Bu4NF / tetrahydrofuran
2: 92 percent / PDC / dimethylformamide
View Scheme
Multi-step reaction with 2 steps
1: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
2: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: (n-Bu)4NF / tetrahydrofuran / 0.17 h / Ambient temperature
2: 92 percent / PDC / dimethylformamide / 2 h / Ambient temperature
View Scheme
(4S,5E,7S,9R,10R)-9,10-epoxy-7-hydroxymethyl-4-isopropyl-5-cyclodecen-1-one
123536-67-4

(4S,5E,7S,9R,10R)-9,10-epoxy-7-hydroxymethyl-4-isopropyl-5-cyclodecen-1-one

(3S,8R,9R,10S)-(-)-periplanone-B
61228-92-0

(3S,8R,9R,10S)-(-)-periplanone-B

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 99 percent / n-Bu3P / tetrahydrofuran
2: 90 percent / H2O2 / tetrahydrofuran
3: 86 percent / LiN(TMS)2, MoO5*HMPA*Py / tetrahydrofuran
4: imidazole / dimethylformamide
5: n-BuLi / tetrahydrofuran
6: n-Bu4NF / tetrahydrofuran
7: 92 percent / PDC / dimethylformamide
View Scheme
Multi-step reaction with 7 steps
1: 99 percent / (n-Bu)3P / tetrahydrofuran / 0.83 h / Ambient temperature
2: 90 percent / 35percent H2O2 / tetrahydrofuran / 13 h / Ambient temperature
3: 1) LiN(TMS)2, 2) MoO5*HMPA*py / 1) -78 deg C, 1 h, THF, 2) -20 deg C, 25 min
4: imidazole / dimethylformamide / 17 h / Ambient temperature
5: 1) n-BuLi / 1) THF, hexane, 10 min, 2a) THF, -15 deg C, 10 min, 2b) 20 min, 0 deg C
6: (n-Bu)4NF / tetrahydrofuran / 0.17 h / Ambient temperature
7: 92 percent / PDC / dimethylformamide / 2 h / Ambient temperature
View Scheme
(2S,4S,5E,9R,10R)-9,10-epoxy-2-hydroxy-7-methylene-4-(1-methylethyl)-5-cyclodecene-1-one
113666-34-5

(2S,4S,5E,9R,10R)-9,10-epoxy-2-hydroxy-7-methylene-4-(1-methylethyl)-5-cyclodecene-1-one

(3S,8R,9R,10S)-(-)-periplanone-B
61228-92-0

(3S,8R,9R,10S)-(-)-periplanone-B

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: imidazole / dimethylformamide
2: n-BuLi / tetrahydrofuran
3: n-Bu4NF / tetrahydrofuran
4: 92 percent / PDC / dimethylformamide
View Scheme
Multi-step reaction with 4 steps
1: dimethylformamide / 16 h / 40 °C
2: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
3: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
4: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 4 steps
1: imidazole / dimethylformamide / 17 h / Ambient temperature
2: 1) n-BuLi / 1) THF, hexane, 10 min, 2a) THF, -15 deg C, 10 min, 2b) 20 min, 0 deg C
3: (n-Bu)4NF / tetrahydrofuran / 0.17 h / Ambient temperature
4: 92 percent / PDC / dimethylformamide / 2 h / Ambient temperature
View Scheme
(1S,5S,6R)-5-(2-Ethoxy-ethoxymethyl)-6-((Z)-3-methyl-but-1-enyl)-1-vinyl-cyclohex-2-enol

(1S,5S,6R)-5-(2-Ethoxy-ethoxymethyl)-6-((Z)-3-methyl-but-1-enyl)-1-vinyl-cyclohex-2-enol

(3S,8R,9R,10S)-(-)-periplanone-B
61228-92-0

(3S,8R,9R,10S)-(-)-periplanone-B

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 74 percent / KH, 18-crown-6 / 1,2-dimethoxy-ethane
2: KH, t-BuOOH / tetrahydrofuran
3: PPTS / ethanol
4: 99 percent / n-Bu3P / tetrahydrofuran
5: 90 percent / H2O2 / tetrahydrofuran
6: 86 percent / LiN(TMS)2, MoO5*HMPA*Py / tetrahydrofuran
7: imidazole / dimethylformamide
8: n-BuLi / tetrahydrofuran
9: n-Bu4NF / tetrahydrofuran
10: 92 percent / PDC / dimethylformamide
View Scheme
(2Z,6E)-(5S,8S)-5-(2-Ethoxy-ethoxymethyl)-8-isopropyl-cyclodeca-2,6-dienone

(2Z,6E)-(5S,8S)-5-(2-Ethoxy-ethoxymethyl)-8-isopropyl-cyclodeca-2,6-dienone

(3S,8R,9R,10S)-(-)-periplanone-B
61228-92-0

(3S,8R,9R,10S)-(-)-periplanone-B

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: KH, t-BuOOH / tetrahydrofuran
2: PPTS / ethanol
3: 99 percent / n-Bu3P / tetrahydrofuran
4: 90 percent / H2O2 / tetrahydrofuran
5: 86 percent / LiN(TMS)2, MoO5*HMPA*Py / tetrahydrofuran
6: imidazole / dimethylformamide
7: n-BuLi / tetrahydrofuran
8: n-Bu4NF / tetrahydrofuran
9: 92 percent / PDC / dimethylformamide
View Scheme
(E)-(1R,5S,8S,10R)-8-(2-Ethoxy-ethoxymethyl)-5-isopropyl-11-oxa-bicyclo[8.1.0]undec-6-en-2-one

(E)-(1R,5S,8S,10R)-8-(2-Ethoxy-ethoxymethyl)-5-isopropyl-11-oxa-bicyclo[8.1.0]undec-6-en-2-one

(3S,8R,9R,10S)-(-)-periplanone-B
61228-92-0

(3S,8R,9R,10S)-(-)-periplanone-B

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: PPTS / ethanol
2: 99 percent / n-Bu3P / tetrahydrofuran
3: 90 percent / H2O2 / tetrahydrofuran
4: 86 percent / LiN(TMS)2, MoO5*HMPA*Py / tetrahydrofuran
5: imidazole / dimethylformamide
6: n-BuLi / tetrahydrofuran
7: n-Bu4NF / tetrahydrofuran
8: 92 percent / PDC / dimethylformamide
View Scheme
(E)-(1R,5S,8S,10R)-5-Isopropyl-8-phenylselanylmethyl-11-oxa-bicyclo[8.1.0]undec-6-en-2-one
123453-99-6

(E)-(1R,5S,8S,10R)-5-Isopropyl-8-phenylselanylmethyl-11-oxa-bicyclo[8.1.0]undec-6-en-2-one

(3S,8R,9R,10S)-(-)-periplanone-B
61228-92-0

(3S,8R,9R,10S)-(-)-periplanone-B

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 90 percent / H2O2 / tetrahydrofuran
2: 86 percent / LiN(TMS)2, MoO5*HMPA*Py / tetrahydrofuran
3: imidazole / dimethylformamide
4: n-BuLi / tetrahydrofuran
5: n-Bu4NF / tetrahydrofuran
6: 92 percent / PDC / dimethylformamide
View Scheme
(5S,6R)-5-(2-Ethoxy-ethoxymethyl)-6-((Z)-3-methyl-but-1-enyl)-cyclohex-2-enone

(5S,6R)-5-(2-Ethoxy-ethoxymethyl)-6-((Z)-3-methyl-but-1-enyl)-cyclohex-2-enone

(3S,8R,9R,10S)-(-)-periplanone-B
61228-92-0

(3S,8R,9R,10S)-(-)-periplanone-B

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 86 percent / diethyl ether
2: 74 percent / KH, 18-crown-6 / 1,2-dimethoxy-ethane
3: KH, t-BuOOH / tetrahydrofuran
4: PPTS / ethanol
5: 99 percent / n-Bu3P / tetrahydrofuran
6: 90 percent / H2O2 / tetrahydrofuran
7: 86 percent / LiN(TMS)2, MoO5*HMPA*Py / tetrahydrofuran
8: imidazole / dimethylformamide
9: n-BuLi / tetrahydrofuran
10: n-Bu4NF / tetrahydrofuran
11: 92 percent / PDC / dimethylformamide
View Scheme
(5S,6S)-5-(2-Ethoxy-ethoxymethyl)-6-((1S,2S)-1-hydroxy-3-methyl-2-phenylselanyl-butyl)-cyclohex-2-enone

(5S,6S)-5-(2-Ethoxy-ethoxymethyl)-6-((1S,2S)-1-hydroxy-3-methyl-2-phenylselanyl-butyl)-cyclohex-2-enone

(3S,8R,9R,10S)-(-)-periplanone-B
61228-92-0

(3S,8R,9R,10S)-(-)-periplanone-B

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: MsCl, Et3N / CH2Cl2
2: 86 percent / diethyl ether
3: 74 percent / KH, 18-crown-6 / 1,2-dimethoxy-ethane
4: KH, t-BuOOH / tetrahydrofuran
5: PPTS / ethanol
6: 99 percent / n-Bu3P / tetrahydrofuran
7: 90 percent / H2O2 / tetrahydrofuran
8: 86 percent / LiN(TMS)2, MoO5*HMPA*Py / tetrahydrofuran
9: imidazole / dimethylformamide
10: n-BuLi / tetrahydrofuran
11: n-Bu4NF / tetrahydrofuran
12: 92 percent / PDC / dimethylformamide
View Scheme
(4S,5E)-7-methylene-4-(1-methylethyl)-5-cyclodecene-1-one
105930-38-9

(4S,5E)-7-methylene-4-(1-methylethyl)-5-cyclodecene-1-one

(3S,8R,9R,10S)-(-)-periplanone-B
61228-92-0

(3S,8R,9R,10S)-(-)-periplanone-B

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
2: NaIO4 / methanol; H2O / 22 h
3: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
4: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
5: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
6: dimethylformamide / 16 h / 40 °C
7: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
8: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
9: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 5 steps
2: tBuOOH
3: 1) LiN(TMS)2, 2) MoO5*HMPA*Py / 1) THF, 30 min, 2) -70 degC, 5 min
4: PCC / CH2Cl2 / 5 h / Ambient temperature; Molecular sieves 3A
5: tetrahydrofuran; dimethylsulfoxide / 0.17 h / 0 °C
View Scheme
(R)-3-(1-methylethyl)-6-oxoheptanal dimethylacetal
105897-85-6

(R)-3-(1-methylethyl)-6-oxoheptanal dimethylacetal

(3S,8R,9R,10S)-(-)-periplanone-B
61228-92-0

(3S,8R,9R,10S)-(-)-periplanone-B

Conditions
ConditionsYield
Multi-step reaction with 26 steps
1: 1.) NaH / 1.) dioxane, MeOH, reflux; 2.) reflux, 90 min
2: 62 percent / 1.) KOH / methanol; H2O / 2 h / Heating
3: LiAlH4 / diethyl ether / 1 h / below 10 deg C
4: EtN(i-Pr)2 / CH2Cl2 / 24 h / Heating
5: OsO4, NaIO4 / diethyl ether; H2O / 7 h
6: LiAlH4 / diethyl ether / 0.5 h / below 10 deg C
7: pyridine / Ambient temperature
8: 75 percent AcOH / 1 h / 30 °C
9: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
10: NaOAc / 0.67 h / 130 °C
11: 1 percent NaOMe / methanol / 1 h / Ambient temperature
12: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
13: 1.) NaN(TMS)2; 2.) LiAlH4 / 1.) DME, 50 min, reflux; 2.) Et2O, 0 deg C, 1 h
14: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
15: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
16: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
17: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
18: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
19: NaIO4 / methanol; H2O / 22 h
20: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
21: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
22: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
23: dimethylformamide / 16 h / 40 °C
24: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
25: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
26: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 27 steps
1: 1.) NaH / 1.) dioxane, MeOH, reflux; 2.) reflux, 90 min
2: 62 percent / 1.) KOH / methanol; H2O / 2 h / Heating
3: LiAlH4 / diethyl ether / 1 h / below 10 deg C
4: EtN(i-Pr)2 / CH2Cl2 / 24 h / Heating
5: OsO4, NaIO4 / diethyl ether; H2O / 7 h
6: LiAlH4 / diethyl ether / 0.5 h / below 10 deg C
7: pyridine / Ambient temperature
8: 75 percent AcOH / 1 h / 30 °C
9: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
10: NaOAc / 0.67 h / 130 °C
11: 1 percent NaOMe / methanol / 1 h / Ambient temperature
12: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
13: NaN(TMS)2 / 1,2-dimethoxy-ethane / 0.83 h / Heating
14: 99 percent / LiAlH4 / diethyl ether / 1 h / 0 °C
15: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
16: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
17: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
18: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
19: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
20: NaIO4 / methanol; H2O / 22 h
21: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
22: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
23: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
24: dimethylformamide / 16 h / 40 °C
25: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
26: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
27: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 26 steps
1: 1.) NaH / 1.) dioxane, MeOH, reflux; 2.) reflux, 90 min
2: 62 percent / 1.) KOH / methanol; H2O / 2 h / Heating
3: LiAlH4 / diethyl ether / 1 h / below 10 deg C
4: EtN(i-Pr)2 / CH2Cl2 / 24 h / Heating
5: OsO4, NaIO4 / diethyl ether; H2O / 7 h
6: LiAlH4 / diethyl ether / 0.5 h / below 10 deg C
7: pyridine / Ambient temperature
8: 75 percent AcOH / 1 h / 30 °C
9: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
10: NaOAc, Ac2O / 0.67 h / 130 °C
11: 1 percent NaOMe / methanol / 1 h / Ambient temperature
12: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
13: 1.) NaN(TMS)2; 2.) LiAlH4 / 1.) DME, 50 min, reflux; 2.) Et2O, 0 deg C, 1 h
14: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
15: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
16: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
17: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
18: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
19: NaIO4 / methanol; H2O / 22 h
20: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
21: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
22: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
23: dimethylformamide / 16 h / 40 °C
24: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
25: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
26: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 27 steps
1: 1.) NaH / 1.) dioxane, MeOH, reflux; 2.) reflux, 90 min
2: 62 percent / 1.) KOH / methanol; H2O / 2 h / Heating
3: LiAlH4 / diethyl ether / 1 h / below 10 deg C
4: EtN(i-Pr)2 / CH2Cl2 / 24 h / Heating
5: OsO4, NaIO4 / diethyl ether; H2O / 7 h
6: LiAlH4 / diethyl ether / 0.5 h / below 10 deg C
7: pyridine / Ambient temperature
8: 75 percent AcOH / 1 h / 30 °C
9: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
10: NaOAc, Ac2O / 0.67 h / 130 °C
11: 1 percent NaOMe / methanol / 1 h / Ambient temperature
12: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
13: NaN(TMS)2 / 1,2-dimethoxy-ethane / 0.83 h / Heating
14: 99 percent / LiAlH4 / diethyl ether / 1 h / 0 °C
15: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
16: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
17: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
18: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
19: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
20: NaIO4 / methanol; H2O / 22 h
21: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
22: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
23: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
24: dimethylformamide / 16 h / 40 °C
25: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
26: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
27: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
(R)-3-(1-methylethyl)-6-oxo-9-decenal dimethylacetal
105897-86-7

(R)-3-(1-methylethyl)-6-oxo-9-decenal dimethylacetal

(3S,8R,9R,10S)-(-)-periplanone-B
61228-92-0

(3S,8R,9R,10S)-(-)-periplanone-B

Conditions
ConditionsYield
Multi-step reaction with 24 steps
1: LiAlH4 / diethyl ether / 1 h / below 10 deg C
2: EtN(i-Pr)2 / CH2Cl2 / 24 h / Heating
3: OsO4, NaIO4 / diethyl ether; H2O / 7 h
4: LiAlH4 / diethyl ether / 0.5 h / below 10 deg C
5: pyridine / Ambient temperature
6: 75 percent AcOH / 1 h / 30 °C
7: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
8: NaOAc / 0.67 h / 130 °C
9: 1 percent NaOMe / methanol / 1 h / Ambient temperature
10: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
11: 1.) NaN(TMS)2; 2.) LiAlH4 / 1.) DME, 50 min, reflux; 2.) Et2O, 0 deg C, 1 h
12: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
13: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
14: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
15: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
16: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
17: NaIO4 / methanol; H2O / 22 h
18: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
19: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
20: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
21: dimethylformamide / 16 h / 40 °C
22: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
23: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
24: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 25 steps
1: LiAlH4 / diethyl ether / 1 h / below 10 deg C
2: EtN(i-Pr)2 / CH2Cl2 / 24 h / Heating
3: OsO4, NaIO4 / diethyl ether; H2O / 7 h
4: LiAlH4 / diethyl ether / 0.5 h / below 10 deg C
5: pyridine / Ambient temperature
6: 75 percent AcOH / 1 h / 30 °C
7: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
8: NaOAc / 0.67 h / 130 °C
9: 1 percent NaOMe / methanol / 1 h / Ambient temperature
10: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
11: NaN(TMS)2 / 1,2-dimethoxy-ethane / 0.83 h / Heating
12: 99 percent / LiAlH4 / diethyl ether / 1 h / 0 °C
13: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
14: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
15: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
16: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
17: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
18: NaIO4 / methanol; H2O / 22 h
19: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
20: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
21: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
22: dimethylformamide / 16 h / 40 °C
23: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
24: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
25: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 24 steps
1: LiAlH4 / diethyl ether / 1 h / below 10 deg C
2: EtN(i-Pr)2 / CH2Cl2 / 24 h / Heating
3: OsO4, NaIO4 / diethyl ether; H2O / 7 h
4: LiAlH4 / diethyl ether / 0.5 h / below 10 deg C
5: pyridine / Ambient temperature
6: 75 percent AcOH / 1 h / 30 °C
7: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
8: NaOAc, Ac2O / 0.67 h / 130 °C
9: 1 percent NaOMe / methanol / 1 h / Ambient temperature
10: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
11: 1.) NaN(TMS)2; 2.) LiAlH4 / 1.) DME, 50 min, reflux; 2.) Et2O, 0 deg C, 1 h
12: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
13: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
14: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
15: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
16: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
17: NaIO4 / methanol; H2O / 22 h
18: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
19: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
20: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
21: dimethylformamide / 16 h / 40 °C
22: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
23: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
24: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 25 steps
1: LiAlH4 / diethyl ether / 1 h / below 10 deg C
2: EtN(i-Pr)2 / CH2Cl2 / 24 h / Heating
3: OsO4, NaIO4 / diethyl ether; H2O / 7 h
4: LiAlH4 / diethyl ether / 0.5 h / below 10 deg C
5: pyridine / Ambient temperature
6: 75 percent AcOH / 1 h / 30 °C
7: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
8: NaOAc, Ac2O / 0.67 h / 130 °C
9: 1 percent NaOMe / methanol / 1 h / Ambient temperature
10: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
11: NaN(TMS)2 / 1,2-dimethoxy-ethane / 0.83 h / Heating
12: 99 percent / LiAlH4 / diethyl ether / 1 h / 0 °C
13: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
14: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
15: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
16: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
17: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
18: NaIO4 / methanol; H2O / 22 h
19: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
20: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
21: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
22: dimethylformamide / 16 h / 40 °C
23: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
24: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
25: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
(1RS,4S,5E)-7-methylene-4-(1-methylethyl)-5-cyclodecene-1-ol
105897-92-5, 113666-31-2, 113666-38-9

(1RS,4S,5E)-7-methylene-4-(1-methylethyl)-5-cyclodecene-1-ol

(3S,8R,9R,10S)-(-)-periplanone-B
61228-92-0

(3S,8R,9R,10S)-(-)-periplanone-B

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
2: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
3: NaIO4 / methanol; H2O / 22 h
4: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
5: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
6: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
7: dimethylformamide / 16 h / 40 °C
8: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
9: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
10: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 6 steps
1: 72 percent / PCC-NaOH / CH2Cl2
3: tBuOOH
4: 1) LiN(TMS)2, 2) MoO5*HMPA*Py / 1) THF, 30 min, 2) -70 degC, 5 min
5: PCC / CH2Cl2 / 5 h / Ambient temperature; Molecular sieves 3A
6: tetrahydrofuran; dimethylsulfoxide / 0.17 h / 0 °C
View Scheme
(1RS,2E,4S,7RS)-7-hydroxy-4-(1-methylethyl)-1-phenylthio-2-cyclodecene-1-methyl benzoate
105897-91-4

(1RS,2E,4S,7RS)-7-hydroxy-4-(1-methylethyl)-1-phenylthio-2-cyclodecene-1-methyl benzoate

(3S,8R,9R,10S)-(-)-periplanone-B
61228-92-0

(3S,8R,9R,10S)-(-)-periplanone-B

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
2: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
3: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
4: NaIO4 / methanol; H2O / 22 h
5: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
6: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
7: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
8: dimethylformamide / 16 h / 40 °C
9: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
10: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
11: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 7 steps
1: 82 percent / sodium naphthalenide / tetrahydrofuran / 0.08 h / -78 °C
2: 72 percent / PCC-NaOH / CH2Cl2
4: tBuOOH
5: 1) LiN(TMS)2, 2) MoO5*HMPA*Py / 1) THF, 30 min, 2) -70 degC, 5 min
6: PCC / CH2Cl2 / 5 h / Ambient temperature; Molecular sieves 3A
7: tetrahydrofuran; dimethylsulfoxide / 0.17 h / 0 °C
View Scheme
(2Z,6E,8S)-5-methylene-8-(1-methylethyl)-2,6-cyclodecadien-1-one
113666-33-4

(2Z,6E,8S)-5-methylene-8-(1-methylethyl)-2,6-cyclodecadien-1-one

(3S,8R,9R,10S)-(-)-periplanone-B
61228-92-0

(3S,8R,9R,10S)-(-)-periplanone-B

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
2: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
3: dimethylformamide / 16 h / 40 °C
4: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
5: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
6: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 4 steps
1: tBuOOH
2: 1) LiN(TMS)2, 2) MoO5*HMPA*Py / 1) THF, 30 min, 2) -70 degC, 5 min
3: PCC / CH2Cl2 / 5 h / Ambient temperature; Molecular sieves 3A
4: tetrahydrofuran; dimethylsulfoxide / 0.17 h / 0 °C
View Scheme
(R)-8-(2,2-Dimethoxy-ethyl)-9-methyl-dec-1-en-5-ol
113590-01-5

(R)-8-(2,2-Dimethoxy-ethyl)-9-methyl-dec-1-en-5-ol

(3S,8R,9R,10S)-(-)-periplanone-B
61228-92-0

(3S,8R,9R,10S)-(-)-periplanone-B

Conditions
ConditionsYield
Multi-step reaction with 23 steps
1: EtN(i-Pr)2 / CH2Cl2 / 24 h / Heating
2: OsO4, NaIO4 / diethyl ether; H2O / 7 h
3: LiAlH4 / diethyl ether / 0.5 h / below 10 deg C
4: pyridine / Ambient temperature
5: 75 percent AcOH / 1 h / 30 °C
6: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
7: NaOAc / 0.67 h / 130 °C
8: 1 percent NaOMe / methanol / 1 h / Ambient temperature
9: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
10: 1.) NaN(TMS)2; 2.) LiAlH4 / 1.) DME, 50 min, reflux; 2.) Et2O, 0 deg C, 1 h
11: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
12: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
13: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
14: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
15: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
16: NaIO4 / methanol; H2O / 22 h
17: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
18: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
19: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
20: dimethylformamide / 16 h / 40 °C
21: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
22: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
23: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 24 steps
1: EtN(i-Pr)2 / CH2Cl2 / 24 h / Heating
2: OsO4, NaIO4 / diethyl ether; H2O / 7 h
3: LiAlH4 / diethyl ether / 0.5 h / below 10 deg C
4: pyridine / Ambient temperature
5: 75 percent AcOH / 1 h / 30 °C
6: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
7: NaOAc / 0.67 h / 130 °C
8: 1 percent NaOMe / methanol / 1 h / Ambient temperature
9: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
10: NaN(TMS)2 / 1,2-dimethoxy-ethane / 0.83 h / Heating
11: 99 percent / LiAlH4 / diethyl ether / 1 h / 0 °C
12: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
13: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
14: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
15: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
16: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
17: NaIO4 / methanol; H2O / 22 h
18: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
19: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
20: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
21: dimethylformamide / 16 h / 40 °C
22: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
23: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
24: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 23 steps
1: EtN(i-Pr)2 / CH2Cl2 / 24 h / Heating
2: OsO4, NaIO4 / diethyl ether; H2O / 7 h
3: LiAlH4 / diethyl ether / 0.5 h / below 10 deg C
4: pyridine / Ambient temperature
5: 75 percent AcOH / 1 h / 30 °C
6: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
7: NaOAc, Ac2O / 0.67 h / 130 °C
8: 1 percent NaOMe / methanol / 1 h / Ambient temperature
9: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
10: 1.) NaN(TMS)2; 2.) LiAlH4 / 1.) DME, 50 min, reflux; 2.) Et2O, 0 deg C, 1 h
11: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
12: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
13: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
14: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
15: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
16: NaIO4 / methanol; H2O / 22 h
17: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
18: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
19: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
20: dimethylformamide / 16 h / 40 °C
21: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
22: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
23: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 24 steps
1: EtN(i-Pr)2 / CH2Cl2 / 24 h / Heating
2: OsO4, NaIO4 / diethyl ether; H2O / 7 h
3: LiAlH4 / diethyl ether / 0.5 h / below 10 deg C
4: pyridine / Ambient temperature
5: 75 percent AcOH / 1 h / 30 °C
6: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
7: NaOAc, Ac2O / 0.67 h / 130 °C
8: 1 percent NaOMe / methanol / 1 h / Ambient temperature
9: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
10: NaN(TMS)2 / 1,2-dimethoxy-ethane / 0.83 h / Heating
11: 99 percent / LiAlH4 / diethyl ether / 1 h / 0 °C
12: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
13: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
14: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
15: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
16: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
17: NaIO4 / methanol; H2O / 22 h
18: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
19: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
20: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
21: dimethylformamide / 16 h / 40 °C
22: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
23: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
24: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
(R)-7-(2,2-Dimethoxy-ethyl)-4-(2-methoxy-ethoxymethoxy)-8-methyl-nonan-1-ol
113590-03-7

(R)-7-(2,2-Dimethoxy-ethyl)-4-(2-methoxy-ethoxymethoxy)-8-methyl-nonan-1-ol

(3S,8R,9R,10S)-(-)-periplanone-B
61228-92-0

(3S,8R,9R,10S)-(-)-periplanone-B

Conditions
ConditionsYield
Multi-step reaction with 20 steps
1: pyridine / Ambient temperature
2: 75 percent AcOH / 1 h / 30 °C
3: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
4: NaOAc / 0.67 h / 130 °C
5: 1 percent NaOMe / methanol / 1 h / Ambient temperature
6: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
7: 1.) NaN(TMS)2; 2.) LiAlH4 / 1.) DME, 50 min, reflux; 2.) Et2O, 0 deg C, 1 h
8: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
9: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
10: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
11: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
12: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
13: NaIO4 / methanol; H2O / 22 h
14: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
15: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
16: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
17: dimethylformamide / 16 h / 40 °C
18: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
19: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
20: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 21 steps
1: pyridine / Ambient temperature
2: 75 percent AcOH / 1 h / 30 °C
3: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
4: NaOAc / 0.67 h / 130 °C
5: 1 percent NaOMe / methanol / 1 h / Ambient temperature
6: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
7: NaN(TMS)2 / 1,2-dimethoxy-ethane / 0.83 h / Heating
8: 99 percent / LiAlH4 / diethyl ether / 1 h / 0 °C
9: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
10: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
11: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
12: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
13: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
14: NaIO4 / methanol; H2O / 22 h
15: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
16: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
17: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
18: dimethylformamide / 16 h / 40 °C
19: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
20: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
21: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 20 steps
1: pyridine / Ambient temperature
2: 75 percent AcOH / 1 h / 30 °C
3: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
4: NaOAc, Ac2O / 0.67 h / 130 °C
5: 1 percent NaOMe / methanol / 1 h / Ambient temperature
6: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
7: 1.) NaN(TMS)2; 2.) LiAlH4 / 1.) DME, 50 min, reflux; 2.) Et2O, 0 deg C, 1 h
8: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
9: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
10: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
11: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
12: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
13: NaIO4 / methanol; H2O / 22 h
14: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
15: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
16: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
17: dimethylformamide / 16 h / 40 °C
18: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
19: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
20: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 21 steps
1: pyridine / Ambient temperature
2: 75 percent AcOH / 1 h / 30 °C
3: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
4: NaOAc, Ac2O / 0.67 h / 130 °C
5: 1 percent NaOMe / methanol / 1 h / Ambient temperature
6: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
7: NaN(TMS)2 / 1,2-dimethoxy-ethane / 0.83 h / Heating
8: 99 percent / LiAlH4 / diethyl ether / 1 h / 0 °C
9: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
10: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
11: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
12: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
13: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
14: NaIO4 / methanol; H2O / 22 h
15: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
16: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
17: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
18: dimethylformamide / 16 h / 40 °C
19: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
20: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
21: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
(3R,6RS)-6-(2-methoxyethoxymethoxy)-3-(1-methylethyl)-9-decenal dimethylacetal
113589-93-8

(3R,6RS)-6-(2-methoxyethoxymethoxy)-3-(1-methylethyl)-9-decenal dimethylacetal

(3S,8R,9R,10S)-(-)-periplanone-B
61228-92-0

(3S,8R,9R,10S)-(-)-periplanone-B

Conditions
ConditionsYield
Multi-step reaction with 22 steps
1: OsO4, NaIO4 / diethyl ether; H2O / 7 h
2: LiAlH4 / diethyl ether / 0.5 h / below 10 deg C
3: pyridine / Ambient temperature
4: 75 percent AcOH / 1 h / 30 °C
5: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
6: NaOAc / 0.67 h / 130 °C
7: 1 percent NaOMe / methanol / 1 h / Ambient temperature
8: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
9: 1.) NaN(TMS)2; 2.) LiAlH4 / 1.) DME, 50 min, reflux; 2.) Et2O, 0 deg C, 1 h
10: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
11: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
12: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
13: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
14: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
15: NaIO4 / methanol; H2O / 22 h
16: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
17: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
18: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
19: dimethylformamide / 16 h / 40 °C
20: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
21: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
22: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 23 steps
1: OsO4, NaIO4 / diethyl ether; H2O / 7 h
2: LiAlH4 / diethyl ether / 0.5 h / below 10 deg C
3: pyridine / Ambient temperature
4: 75 percent AcOH / 1 h / 30 °C
5: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
6: NaOAc / 0.67 h / 130 °C
7: 1 percent NaOMe / methanol / 1 h / Ambient temperature
8: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
9: NaN(TMS)2 / 1,2-dimethoxy-ethane / 0.83 h / Heating
10: 99 percent / LiAlH4 / diethyl ether / 1 h / 0 °C
11: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
12: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
13: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
14: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
15: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
16: NaIO4 / methanol; H2O / 22 h
17: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
18: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
19: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
20: dimethylformamide / 16 h / 40 °C
21: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
22: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
23: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 22 steps
1: OsO4, NaIO4 / diethyl ether; H2O / 7 h
2: LiAlH4 / diethyl ether / 0.5 h / below 10 deg C
3: pyridine / Ambient temperature
4: 75 percent AcOH / 1 h / 30 °C
5: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
6: NaOAc, Ac2O / 0.67 h / 130 °C
7: 1 percent NaOMe / methanol / 1 h / Ambient temperature
8: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
9: 1.) NaN(TMS)2; 2.) LiAlH4 / 1.) DME, 50 min, reflux; 2.) Et2O, 0 deg C, 1 h
10: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
11: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
12: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
13: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
14: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
15: NaIO4 / methanol; H2O / 22 h
16: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
17: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
18: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
19: dimethylformamide / 16 h / 40 °C
20: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
21: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
22: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 23 steps
1: OsO4, NaIO4 / diethyl ether; H2O / 7 h
2: LiAlH4 / diethyl ether / 0.5 h / below 10 deg C
3: pyridine / Ambient temperature
4: 75 percent AcOH / 1 h / 30 °C
5: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
6: NaOAc, Ac2O / 0.67 h / 130 °C
7: 1 percent NaOMe / methanol / 1 h / Ambient temperature
8: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
9: NaN(TMS)2 / 1,2-dimethoxy-ethane / 0.83 h / Heating
10: 99 percent / LiAlH4 / diethyl ether / 1 h / 0 °C
11: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
12: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
13: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
14: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
15: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
16: NaIO4 / methanol; H2O / 22 h
17: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
18: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
19: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
20: dimethylformamide / 16 h / 40 °C
21: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
22: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
23: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
(R)-2-Allyl-6-(2,2-dimethoxy-ethyl)-7-methyl-3-oxo-octanoic acid methyl ester
112193-61-0, 115042-30-3, 115042-31-4

(R)-2-Allyl-6-(2,2-dimethoxy-ethyl)-7-methyl-3-oxo-octanoic acid methyl ester

(3S,8R,9R,10S)-(-)-periplanone-B
61228-92-0

(3S,8R,9R,10S)-(-)-periplanone-B

Conditions
ConditionsYield
Multi-step reaction with 25 steps
1: 62 percent / 1.) KOH / methanol; H2O / 2 h / Heating
2: LiAlH4 / diethyl ether / 1 h / below 10 deg C
3: EtN(i-Pr)2 / CH2Cl2 / 24 h / Heating
4: OsO4, NaIO4 / diethyl ether; H2O / 7 h
5: LiAlH4 / diethyl ether / 0.5 h / below 10 deg C
6: pyridine / Ambient temperature
7: 75 percent AcOH / 1 h / 30 °C
8: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
9: NaOAc / 0.67 h / 130 °C
10: 1 percent NaOMe / methanol / 1 h / Ambient temperature
11: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
12: 1.) NaN(TMS)2; 2.) LiAlH4 / 1.) DME, 50 min, reflux; 2.) Et2O, 0 deg C, 1 h
13: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
14: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
15: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
16: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
17: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
18: NaIO4 / methanol; H2O / 22 h
19: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
20: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
21: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
22: dimethylformamide / 16 h / 40 °C
23: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
24: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
25: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 26 steps
1: 62 percent / 1.) KOH / methanol; H2O / 2 h / Heating
2: LiAlH4 / diethyl ether / 1 h / below 10 deg C
3: EtN(i-Pr)2 / CH2Cl2 / 24 h / Heating
4: OsO4, NaIO4 / diethyl ether; H2O / 7 h
5: LiAlH4 / diethyl ether / 0.5 h / below 10 deg C
6: pyridine / Ambient temperature
7: 75 percent AcOH / 1 h / 30 °C
8: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
9: NaOAc / 0.67 h / 130 °C
10: 1 percent NaOMe / methanol / 1 h / Ambient temperature
11: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
12: NaN(TMS)2 / 1,2-dimethoxy-ethane / 0.83 h / Heating
13: 99 percent / LiAlH4 / diethyl ether / 1 h / 0 °C
14: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
15: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
16: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
17: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
18: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
19: NaIO4 / methanol; H2O / 22 h
20: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
21: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
22: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
23: dimethylformamide / 16 h / 40 °C
24: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
25: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
26: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 25 steps
1: 62 percent / 1.) KOH / methanol; H2O / 2 h / Heating
2: LiAlH4 / diethyl ether / 1 h / below 10 deg C
3: EtN(i-Pr)2 / CH2Cl2 / 24 h / Heating
4: OsO4, NaIO4 / diethyl ether; H2O / 7 h
5: LiAlH4 / diethyl ether / 0.5 h / below 10 deg C
6: pyridine / Ambient temperature
7: 75 percent AcOH / 1 h / 30 °C
8: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
9: NaOAc, Ac2O / 0.67 h / 130 °C
10: 1 percent NaOMe / methanol / 1 h / Ambient temperature
11: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
12: 1.) NaN(TMS)2; 2.) LiAlH4 / 1.) DME, 50 min, reflux; 2.) Et2O, 0 deg C, 1 h
13: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
14: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
15: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
16: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
17: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
18: NaIO4 / methanol; H2O / 22 h
19: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
20: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
21: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
22: dimethylformamide / 16 h / 40 °C
23: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
24: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
25: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 26 steps
1: 62 percent / 1.) KOH / methanol; H2O / 2 h / Heating
2: LiAlH4 / diethyl ether / 1 h / below 10 deg C
3: EtN(i-Pr)2 / CH2Cl2 / 24 h / Heating
4: OsO4, NaIO4 / diethyl ether; H2O / 7 h
5: LiAlH4 / diethyl ether / 0.5 h / below 10 deg C
6: pyridine / Ambient temperature
7: 75 percent AcOH / 1 h / 30 °C
8: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
9: NaOAc, Ac2O / 0.67 h / 130 °C
10: 1 percent NaOMe / methanol / 1 h / Ambient temperature
11: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
12: NaN(TMS)2 / 1,2-dimethoxy-ethane / 0.83 h / Heating
13: 99 percent / LiAlH4 / diethyl ether / 1 h / 0 °C
14: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
15: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
16: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
17: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
18: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
19: NaIO4 / methanol; H2O / 22 h
20: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
21: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
22: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
23: dimethylformamide / 16 h / 40 °C
24: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
25: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
26: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
(R)-7-(2,2-Dimethoxy-ethyl)-4-(2-methoxy-ethoxymethoxy)-8-methyl-nonanal
113590-02-6

(R)-7-(2,2-Dimethoxy-ethyl)-4-(2-methoxy-ethoxymethoxy)-8-methyl-nonanal

(3S,8R,9R,10S)-(-)-periplanone-B
61228-92-0

(3S,8R,9R,10S)-(-)-periplanone-B

Conditions
ConditionsYield
Multi-step reaction with 21 steps
1: LiAlH4 / diethyl ether / 0.5 h / below 10 deg C
2: pyridine / Ambient temperature
3: 75 percent AcOH / 1 h / 30 °C
4: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
5: NaOAc / 0.67 h / 130 °C
6: 1 percent NaOMe / methanol / 1 h / Ambient temperature
7: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
8: 1.) NaN(TMS)2; 2.) LiAlH4 / 1.) DME, 50 min, reflux; 2.) Et2O, 0 deg C, 1 h
9: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
10: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
11: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
12: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
13: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
14: NaIO4 / methanol; H2O / 22 h
15: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
16: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
17: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
18: dimethylformamide / 16 h / 40 °C
19: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
20: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
21: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 22 steps
1: LiAlH4 / diethyl ether / 0.5 h / below 10 deg C
2: pyridine / Ambient temperature
3: 75 percent AcOH / 1 h / 30 °C
4: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
5: NaOAc / 0.67 h / 130 °C
6: 1 percent NaOMe / methanol / 1 h / Ambient temperature
7: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
8: NaN(TMS)2 / 1,2-dimethoxy-ethane / 0.83 h / Heating
9: 99 percent / LiAlH4 / diethyl ether / 1 h / 0 °C
10: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
11: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
12: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
13: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
14: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
15: NaIO4 / methanol; H2O / 22 h
16: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
17: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
18: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
19: dimethylformamide / 16 h / 40 °C
20: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
21: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
22: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 21 steps
1: LiAlH4 / diethyl ether / 0.5 h / below 10 deg C
2: pyridine / Ambient temperature
3: 75 percent AcOH / 1 h / 30 °C
4: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
5: NaOAc, Ac2O / 0.67 h / 130 °C
6: 1 percent NaOMe / methanol / 1 h / Ambient temperature
7: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
8: 1.) NaN(TMS)2; 2.) LiAlH4 / 1.) DME, 50 min, reflux; 2.) Et2O, 0 deg C, 1 h
9: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
10: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
11: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
12: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
13: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
14: NaIO4 / methanol; H2O / 22 h
15: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
16: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
17: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
18: dimethylformamide / 16 h / 40 °C
19: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
20: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
21: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 22 steps
1: LiAlH4 / diethyl ether / 0.5 h / below 10 deg C
2: pyridine / Ambient temperature
3: 75 percent AcOH / 1 h / 30 °C
4: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
5: NaOAc, Ac2O / 0.67 h / 130 °C
6: 1 percent NaOMe / methanol / 1 h / Ambient temperature
7: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
8: NaN(TMS)2 / 1,2-dimethoxy-ethane / 0.83 h / Heating
9: 99 percent / LiAlH4 / diethyl ether / 1 h / 0 °C
10: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
11: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
12: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
13: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
14: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
15: NaIO4 / methanol; H2O / 22 h
16: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
17: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
18: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
19: dimethylformamide / 16 h / 40 °C
20: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
21: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
22: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
(4S,5E)-4-isopropyl-7-methylene-10-phenylthio-5-cyclodecen-1-one
90460-45-0, 105371-09-3, 113666-99-2

(4S,5E)-4-isopropyl-7-methylene-10-phenylthio-5-cyclodecen-1-one

(3S,8R,9R,10S)-(-)-periplanone-B
61228-92-0

(3S,8R,9R,10S)-(-)-periplanone-B

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: NaIO4 / methanol; H2O / 22 h
2: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
3: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
4: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
5: dimethylformamide / 16 h / 40 °C
6: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
7: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
8: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Acetic acid (R)-4-(2-methoxy-ethoxymethoxy)-8-methyl-7-(2-oxo-ethyl)-nonyl ester
113589-94-9

Acetic acid (R)-4-(2-methoxy-ethoxymethoxy)-8-methyl-7-(2-oxo-ethyl)-nonyl ester

(3S,8R,9R,10S)-(-)-periplanone-B
61228-92-0

(3S,8R,9R,10S)-(-)-periplanone-B

Conditions
ConditionsYield
Multi-step reaction with 18 steps
1: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
2: NaOAc / 0.67 h / 130 °C
3: 1 percent NaOMe / methanol / 1 h / Ambient temperature
4: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
5: 1.) NaN(TMS)2; 2.) LiAlH4 / 1.) DME, 50 min, reflux; 2.) Et2O, 0 deg C, 1 h
6: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
7: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
8: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
9: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
10: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
11: NaIO4 / methanol; H2O / 22 h
12: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
13: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
14: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
15: dimethylformamide / 16 h / 40 °C
16: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
17: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
18: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 19 steps
1: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
2: NaOAc / 0.67 h / 130 °C
3: 1 percent NaOMe / methanol / 1 h / Ambient temperature
4: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
5: NaN(TMS)2 / 1,2-dimethoxy-ethane / 0.83 h / Heating
6: 99 percent / LiAlH4 / diethyl ether / 1 h / 0 °C
7: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
8: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
9: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
10: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
11: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
12: NaIO4 / methanol; H2O / 22 h
13: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
14: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
15: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
16: dimethylformamide / 16 h / 40 °C
17: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
18: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
19: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 18 steps
1: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
2: NaOAc, Ac2O / 0.67 h / 130 °C
3: 1 percent NaOMe / methanol / 1 h / Ambient temperature
4: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
5: 1.) NaN(TMS)2; 2.) LiAlH4 / 1.) DME, 50 min, reflux; 2.) Et2O, 0 deg C, 1 h
6: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
7: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
8: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
9: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
10: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
11: NaIO4 / methanol; H2O / 22 h
12: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
13: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
14: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
15: dimethylformamide / 16 h / 40 °C
16: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
17: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
18: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 19 steps
1: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
2: NaOAc, Ac2O / 0.67 h / 130 °C
3: 1 percent NaOMe / methanol / 1 h / Ambient temperature
4: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
5: NaN(TMS)2 / 1,2-dimethoxy-ethane / 0.83 h / Heating
6: 99 percent / LiAlH4 / diethyl ether / 1 h / 0 °C
7: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
8: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
9: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
10: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
11: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
12: NaIO4 / methanol; H2O / 22 h
13: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
14: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
15: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
16: dimethylformamide / 16 h / 40 °C
17: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
18: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
19: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
(3R,6RS)-9-acetoxy-6-(2-methoxyethoxymethoxy)-3-(1-methylethyl)-nonanal dimethylacetal
113603-27-3

(3R,6RS)-9-acetoxy-6-(2-methoxyethoxymethoxy)-3-(1-methylethyl)-nonanal dimethylacetal

(3S,8R,9R,10S)-(-)-periplanone-B
61228-92-0

(3S,8R,9R,10S)-(-)-periplanone-B

Conditions
ConditionsYield
Multi-step reaction with 19 steps
1: 75 percent AcOH / 1 h / 30 °C
2: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
3: NaOAc / 0.67 h / 130 °C
4: 1 percent NaOMe / methanol / 1 h / Ambient temperature
5: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
6: 1.) NaN(TMS)2; 2.) LiAlH4 / 1.) DME, 50 min, reflux; 2.) Et2O, 0 deg C, 1 h
7: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
8: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
9: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
10: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
11: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
12: NaIO4 / methanol; H2O / 22 h
13: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
14: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
15: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
16: dimethylformamide / 16 h / 40 °C
17: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
18: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
19: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 20 steps
1: 75 percent AcOH / 1 h / 30 °C
2: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
3: NaOAc / 0.67 h / 130 °C
4: 1 percent NaOMe / methanol / 1 h / Ambient temperature
5: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
6: NaN(TMS)2 / 1,2-dimethoxy-ethane / 0.83 h / Heating
7: 99 percent / LiAlH4 / diethyl ether / 1 h / 0 °C
8: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
9: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
10: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
11: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
12: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
13: NaIO4 / methanol; H2O / 22 h
14: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
15: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
16: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
17: dimethylformamide / 16 h / 40 °C
18: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
19: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
20: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 19 steps
1: 75 percent AcOH / 1 h / 30 °C
2: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
3: NaOAc, Ac2O / 0.67 h / 130 °C
4: 1 percent NaOMe / methanol / 1 h / Ambient temperature
5: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
6: 1.) NaN(TMS)2; 2.) LiAlH4 / 1.) DME, 50 min, reflux; 2.) Et2O, 0 deg C, 1 h
7: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
8: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
9: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
10: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
11: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
12: NaIO4 / methanol; H2O / 22 h
13: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
14: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
15: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
16: dimethylformamide / 16 h / 40 °C
17: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
18: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
19: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 20 steps
1: 75 percent AcOH / 1 h / 30 °C
2: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min
3: NaOAc, Ac2O / 0.67 h / 130 °C
4: 1 percent NaOMe / methanol / 1 h / Ambient temperature
5: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
6: NaN(TMS)2 / 1,2-dimethoxy-ethane / 0.83 h / Heating
7: 99 percent / LiAlH4 / diethyl ether / 1 h / 0 °C
8: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
9: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
10: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
11: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
12: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
13: NaIO4 / methanol; H2O / 22 h
14: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
15: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
16: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
17: dimethylformamide / 16 h / 40 °C
18: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
19: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
20: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
(4S,5E)-7-methylene-4-(1-methylethyl)-10-phenylsulfinyl-5-cyclodecene-1-one
105329-29-1, 105371-14-0, 113666-32-3

(4S,5E)-7-methylene-4-(1-methylethyl)-10-phenylsulfinyl-5-cyclodecene-1-one

(3S,8R,9R,10S)-(-)-periplanone-B
61228-92-0

(3S,8R,9R,10S)-(-)-periplanone-B

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
2: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
3: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
4: dimethylformamide / 16 h / 40 °C
5: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
6: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
7: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
(1RS,2E,4S,7RS)-7-(2-methoxyethoxymethoxy)-4-(1-methylethyl)-1-phenylthio-2-cyclodecene-1-methanol
113603-28-4

(1RS,2E,4S,7RS)-7-(2-methoxyethoxymethoxy)-4-(1-methylethyl)-1-phenylthio-2-cyclodecene-1-methanol

(3S,8R,9R,10S)-(-)-periplanone-B
61228-92-0

(3S,8R,9R,10S)-(-)-periplanone-B

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
2: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
3: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
4: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
5: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
6: NaIO4 / methanol; H2O / 22 h
7: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
8: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
9: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
10: dimethylformamide / 16 h / 40 °C
11: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
12: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
13: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
methyl (2EZ,5R,8RS)-11-hydroxy-8-(2-methoxyethoxymethoxy)-5-(1-methylethyl)-2-phenylthio-2-undeceonate
113589-96-1

methyl (2EZ,5R,8RS)-11-hydroxy-8-(2-methoxyethoxymethoxy)-5-(1-methylethyl)-2-phenylthio-2-undeceonate

(3S,8R,9R,10S)-(-)-periplanone-B
61228-92-0

(3S,8R,9R,10S)-(-)-periplanone-B

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
2: 1.) NaN(TMS)2; 2.) LiAlH4 / 1.) DME, 50 min, reflux; 2.) Et2O, 0 deg C, 1 h
3: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
4: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
5: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
6: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
7: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
8: NaIO4 / methanol; H2O / 22 h
9: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
10: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
11: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
12: dimethylformamide / 16 h / 40 °C
13: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
14: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
15: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 16 steps
1: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C
2: NaN(TMS)2 / 1,2-dimethoxy-ethane / 0.83 h / Heating
3: 99 percent / LiAlH4 / diethyl ether / 1 h / 0 °C
4: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature
5: 84 percent / TMSCl, NaI / acetonitrile / -10 °C
6: 86 percent / sodium naphtalenide / 0.08 h / -70 °C
7: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature
8: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min
9: NaIO4 / methanol; H2O / 22 h
10: 2,6-di-t-butyl-p-cresol (BHT), CaCO3 / toluene / 6 h / Heating
11: 1.) KH, t-BuOOH / 1.) THF, toluene, below -5 deg C, 5 min; 2.) THF, 0 deg C, 1 h
12: 1.) LiN(TMS)2; 2.) MoO5*HMPA*C5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min
13: dimethylformamide / 16 h / 40 °C
14: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min
15: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature
16: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature
View Scheme

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