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Wuhan Han Sheng New Material Technology Co.，Ltd

Our Advantage: high quality with competitive price High quality standard: BP/USP/EP Enterprise standard All purity customized Fast and safe delivery We have reliable forwarder who can help us deliver our goods more fast and safe. We

Salicylihalamide A CAS NO.198481-99-1

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Qingdao Beluga Import and Export Co., LTD

salicylihalamide A CAS:198481-99-1 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 inter

salicylihalamide A CAS:198481-99-1

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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

Salicylihalamide A

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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

Salicylihalamide A

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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

Salicylihalamide A

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EAST CHEMSOURCES LIMITED

factory?direct?saleAppearance:White Powder Storage:Store In Dry, Cool And Ventilated Place Package:25kg/drum, also according to the clients requirement Application:It is widely used as a thickener, emulsifier and stabilizer Transportation:By Sea Or B

Salicylihalamide A CAS NO.198481-99-1

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Shandong Mopai Biotechnology Co., LTD

Shandong Mopai Biotechnology 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 chemicals. W

Salicylihalamide A CAS NO.198481-99-1

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KAISA GROUP INC

1.Applied in food field.it can improve the immune system and prolong life. 2.Appliedin cosmetic field.it can improve the skin care. 3.Applied in pharmaceutical field.it can treat various dieases. 4.Our product quality assurance will make our customer

Salicylihalamide A CAS NO.198481-99-1

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Bluecrystal chem-union

We are a Union of chemistry in China, consists of chemists，engineers, laboratories,factories in China. We organize surplus capacity of R&D and production as well as custom synthesis for chemical products and chemical business project. We are supp

Salicylihalamide A CAS NO.198481-99-1

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Hebei Mojin Biotechnology Co.,Ltd

1, High quality with competitive price:2, Fast and safe delivery3.Excellent pre-sales and after-sales service4. Well-trained and professional technologist and sales with rich experience in the field for 5-10 yearsAppearance:see detailed specification

Salicylihalamide A

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Xi`an Eastling Biotech Co., Ltd.

high purity lowest priceAppearance:solid or liquid Storage:in sealed air resistant place Package:Foil bag; Drum; Plastic bottle Application:Pharma;Industry;Agricultural Transportation:by sea or air Port:Beijing or Guangzhou

Salicylihalamide A

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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.

Salicylihalamide A

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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

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Hubei Langyou International Trading Co., Ltd

Salicylihalamide A CAS NO.198481-99-1 Application:Salicylihalamide A CAS NO.198481-99-1

Salicylihalamide A CAS NO.198481-99-1

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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

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Hunan Longxianng Runhui Trading Co.,Ltd

Salicylihalamide A CAS NO.198481-99-1Appearance:off-white fine crystalline powder Storage:Dry and ventilated Package:Standard or as customer's require Application:intermediates Transportation:By express (Door to door) such as FEDEX, DHL, EMS for smal

Salicylihalamide A CAS NO.198481-99-1

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Shanghai Chinqesen Biotechnology Co., Ltd.

Good Quality Package:1kg/bag Application:Medical or chemical Transportation:Air/Train/Sea Port:Shenzhen

198481-99-1

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Saiwante (shanghai) New Material Technology Co., Ltd.

Stable supply of goods and provision of high-quality services Application:As raw materials in the field of medicine and biology

Salicylihalamide A CAS NO.198481-99-1

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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

Salicylihalamide A

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HuBei Ipure Biotech CO.,ltd

HuBei ipure is a diversified product production and operation enterprise, with API, pharma intermediates, and other fine chemicals as well as R&D and pigments development and sales as one of the large enterprises, with more than 130 acres of pl

Salicylihalamide A

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Chengdu Push Bio-technology Co., Ltd

Chengdu Push Bio-technology Co., Ltd. provides more than 4,000 natural monomeric substances, including approximately 6,000 products at different grades, specifications and purities. We have specialized in the R&D of medicinally active ingredients sta

Salicylihalamide A

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Hubei Jusheng Technology Co., Ltd.,

1,Best Quality: Our products have exported to Germany, Spain, UK, USA, Australia, Middle East, and so on other countries, and we have got very good feedback from our customers.so

Salicylihalamide A CAS NO.198481-99-1

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changchun tuocai technology co.,ltld

Salicylihalamide A CAS NO.198481-99-1Appearance:off-white fine crystalline powder Storage:Dry and ventilated Package:Standard or as customer's require Application:intermediates Transportation:Delivery by EMS, DHL, FEDEX, UPS, TNT

Salicylihalamide A CAS NO.198481-99-1

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Taizhou volsen chemical Co., Ltd

We are a trading company aiming at providing high-quality services to customers. Established for many years, with good reputation in the industry Storage:Sealed and preserved Application:Fine chemical intermediates, used as the main raw material for

Salicylihalamide A CAS NO.198481-99-1

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Nanjing Raymon Biotech Co., Ltd.

Salicylihalamide A CAS NO.198481-99-1Appearance:off-white fine crystalline powder Storage:Store in dry and cool condition Package:25kg or according to cutomer's demand Application:Chemical research/Pharmaceutical intermediates Transportation:By Sea,b

Salicylihalamide A CAS NO.198481-99-1

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Hebei Minshang Biotechnology Co., Ltd

Salicylihalamide A CAS NO.198481-99-1 Application:intermediates

198481-99-1

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Shanghai PengMo Biotechnology Co.,Ltd

Salicylihalamide A CAS NO.198481-99-1Appearance:off-white fine crystalline powder Storage:Dry and ventilated Package:Standard or as customer's require Application:intermediates Transportation:Delivery by EMS, DHL, FEDEX, UPS, TNT

Salicylihalamide A CAS NO.198481-99-1

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Hangzhou Fenjun Chemical Co Ltd.

Salicylihalamide A CAS NO.198481-99-1 Application:Salicylihalamide A CAS NO.198481-99-1

Salicylihalamide A CAS NO.198481-99-1

Cas:198481-99-1

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Hebei Ruishun Trade Co.,Ltd

Supply top quality products with a reasonable price Application:api

198481-99-1

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View More

Synthetic route

bis[teri-butyl(dimethyl)silyl]-salicylihalamide
350794-14-8

bis[teri-butyl(dimethyl)silyl]-salicylihalamide

(-)-salicylihalamide A
198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
With pyridine hydrogenfluoride In tetrahydrofuran; pyridine for 72h;78%
With pyridine hydrogenfluoride In tetrahydrofuran at 23℃; for 72h;75%
2-allyl-6-methoxy-benzoic acid
325172-28-9

2-allyl-6-methoxy-benzoic acid

(-)-salicylihalamide A
198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1: 84 percent / triphenylphosphine; diethyl azodicarboxylate / benzene / 24 h
2: (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 0.67 h / 20 °C
3: 98 percent / DDQ; buffer / CH2Cl2; H2O / 0.75 h / 20 °C / pH 7
4: 98 percent / Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
5: 82 percent / BBr3 / CH2Cl2 / 3 h / -78 °C
6: 97 percent / sodium chlorite; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 1 h
7: triethylamine / CH2Cl2 / 2 h / 20 °C
8: 21 mg / K2CO3; H2O / methanol; tetrahydrofuran / 0.08 h / 20 °C
9: N,N-diisopropylethylamine / acetone / 0 - 20 °C
10: sodium azide / acetone; H2O / 0.5 h / 20 °C
11: toluene / 0.25 h / 110 °C
12: 21.6 mg / toluene / 0.17 h / Heating
13: 81 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran; benzene / 0.17 h / 0 °C
14: tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C
15: 2.6 mg / HF*py / tetrahydrofuran; pyridine / 48 h / 20 °C
View Scheme
Multi-step reaction with 12 steps
1.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
2.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
3.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
4.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
5.1: NaH / tetrahydrofuran / 1 h / 0 °C
6.1: 64 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
7.1: Ba(OH)2*8H2O / tetrahydrofuran / 20 °C
8.1: imidazole; DMAP / dimethylformamide / 20 °C
9.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
10.1: benzene / 6 h / 75 °C
11.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
11.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
12.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 12 steps
1.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
2.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
3.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
4.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
5.1: 93 percent / NaH / tetrahydrofuran / 1 h / 0 °C
6.1: 81 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
7.1: 92 percent / imidazole; DMAP / dimethylformamide / 10 h / 20 °C
8.1: 96 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran / 4 h / 20 °C
9.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
10.1: benzene / 6 h / 75 °C
11.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
11.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
12.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 9 steps
1: DEAD; PPh3 / diethyl ether / 1 h / 0 - 20 °C
2: bis(tricyclohexylphosphine)benzylidine ruthenium(VI) Cl2 / CH2Cl2 / 3 h / Heating
3: BBr3 / CH2Cl2 / 0.5 h / -78 °C
4: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 0.5 h / 20 °C
5: DIPEA; DMAP / dimethylformamide / 1 h / 70 °C
6: TMSOTf / 1,2-dichloro-ethane / 2 h / 20 °C
7: NaH / various solvent(s) / 4.5 h / 60 °C
8: TBAF / tetrahydrofuran / 1 h / 20 °C
9: TBAF; HMPA / tetrahydrofuran / 48 h / 40 °C
View Scheme
Multi-step reaction with 9 steps
1: DEAD; PPh3 / diethyl ether / 1 h / 0 - 20 °C
2: bis(tricyclohexylphosphine)benzylidine ruthenium(VI) Cl2 / CH2Cl2 / 3 h / Heating
3: BBr3 / CH2Cl2 / 0.5 h / -78 °C
4: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 0.5 h / 20 °C
5: DIPEA; DMAP / dimethylformamide / 1 h / 70 °C
6: TMSOTf / 1,2-dichloro-ethane / 2 h / 20 °C
7: NaH / various solvent(s) / 4.5 h / 60 °C
8: TBAF / tetrahydrofuran / 1 h / 20 °C
9: TBAF; HMPA / tetrahydrofuran / 48 h / 40 °C
View Scheme
(7S,9R,10S,12E)-(4-methoxy-9-methoxymethoxy-10-methyl-5-oxo-7,8,9,10,11,14-hexahydro[5H]-6-oxa-benzocyclododecen-7-yl)-acetaldehyde
398478-59-6

(7S,9R,10S,12E)-(4-methoxy-9-methoxymethoxy-10-methyl-5-oxo-7,8,9,10,11,14-hexahydro[5H]-6-oxa-benzocyclododecen-7-yl)-acetaldehyde

(-)-salicylihalamide A
198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: NaH / tetrahydrofuran / 1 h / 0 °C
2.1: 64 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
3.1: Ba(OH)2*8H2O / tetrahydrofuran / 20 °C
4.1: imidazole; DMAP / dimethylformamide / 20 °C
5.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
6.1: benzene / 6 h / 75 °C
7.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
7.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
8.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 8 steps
1.1: 93 percent / NaH / tetrahydrofuran / 1 h / 0 °C
2.1: 81 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
3.1: 92 percent / imidazole; DMAP / dimethylformamide / 10 h / 20 °C
4.1: 96 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran / 4 h / 20 °C
5.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
6.1: benzene / 6 h / 75 °C
7.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
7.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
8.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 87 percent / CrCl2 / tetrahydrofuran; dioxane / 16 h / 20 °C
2: 88 percent / BBr3 / CH2Cl2 / 1 h / -78 °C
3: copper(I) thiophene-2-carboxylate; Rb2CO3 / N,N-dimethyl-acetamide / 2 h / 90 °C
View Scheme
Multi-step reaction with 7 steps
1.1: NaH / tetrahydrofuran / 0 °C
2.1: 92 percent / BBr3 / CH2Cl2 / -78 °C
3.1: 95 percent / imidazole / dimethylformamide
4.1: 97 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran
5.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
6.1: benzene / 6 h / 75 °C
7.1: t-BuLi / diethyl ether; tetrahydrofuran / 0.75 h / -78 °C
7.2: diethyl ether; tetrahydrofuran / -78 - 0 °C
7.3: HF*pyridine / pyridine; tetrahydrofuran / 48 h / 20 °C
View Scheme
(12E)-(7S,9R,10S)-7-(2-hydroxyethyl)-4-methoxy-9-methoxymethoxy-10-methyl-7,8,9,10,11,14-hexahydro-6-oxa-benzocyclodecen-5-one
320573-55-5

(12E)-(7S,9R,10S)-7-(2-hydroxyethyl)-4-methoxy-9-methoxymethoxy-10-methyl-7,8,9,10,11,14-hexahydro-6-oxa-benzocyclodecen-5-one

(-)-salicylihalamide A
198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
2.1: NaH / tetrahydrofuran / 1 h / 0 °C
3.1: 64 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
4.1: Ba(OH)2*8H2O / tetrahydrofuran / 20 °C
5.1: imidazole; DMAP / dimethylformamide / 20 °C
6.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
7.1: benzene / 6 h / 75 °C
8.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
8.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
9.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 9 steps
1.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
2.1: 93 percent / NaH / tetrahydrofuran / 1 h / 0 °C
3.1: 81 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
4.1: 92 percent / imidazole; DMAP / dimethylformamide / 10 h / 20 °C
5.1: 96 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran / 4 h / 20 °C
6.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
7.1: benzene / 6 h / 75 °C
8.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
8.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
9.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: 87 percent / Dess-Martin periodinane / CH2Cl2 / 18 h / 20 °C
2: 87 percent / CrCl2 / tetrahydrofuran; dioxane / 16 h / 20 °C
3: 88 percent / BBr3 / CH2Cl2 / 1 h / -78 °C
4: copper(I) thiophene-2-carboxylate; Rb2CO3 / N,N-dimethyl-acetamide / 2 h / 90 °C
View Scheme
Multi-step reaction with 8 steps
1.1: Dess-Martin periodinane / CH2Cl2
2.1: NaH / tetrahydrofuran / 0 °C
3.1: 92 percent / BBr3 / CH2Cl2 / -78 °C
4.1: 95 percent / imidazole / dimethylformamide
5.1: 97 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran
6.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
7.1: benzene / 6 h / 75 °C
8.1: t-BuLi / diethyl ether; tetrahydrofuran / 0.75 h / -78 °C
8.2: diethyl ether; tetrahydrofuran / -78 - 0 °C
8.3: HF*pyridine / pyridine; tetrahydrofuran / 48 h / 20 °C
View Scheme
(3S,5R,6S,E)-14-methoxy-3-(2-((4-methoxybenzyl)oxy)-ethyl)-5-(methoxymethoxy)-6-methyl-3,4,5,6,7,10-hexahydro-1H-benzo[c][1]oxacyclododecin-1-one
398478-58-5

(3S,5R,6S,E)-14-methoxy-3-(2-((4-methoxybenzyl)oxy)-ethyl)-5-(methoxymethoxy)-6-methyl-3,4,5,6,7,10-hexahydro-1H-benzo[c][1]oxacyclododecin-1-one

(-)-salicylihalamide A
198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
2.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
3.1: NaH / tetrahydrofuran / 1 h / 0 °C
4.1: 64 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
5.1: Ba(OH)2*8H2O / tetrahydrofuran / 20 °C
6.1: imidazole; DMAP / dimethylformamide / 20 °C
7.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
8.1: benzene / 6 h / 75 °C
9.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
9.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
10.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 10 steps
1.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
2.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
3.1: 93 percent / NaH / tetrahydrofuran / 1 h / 0 °C
4.1: 81 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
5.1: 92 percent / imidazole; DMAP / dimethylformamide / 10 h / 20 °C
6.1: 96 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran / 4 h / 20 °C
7.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
8.1: benzene / 6 h / 75 °C
9.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
9.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
10.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1: 94 percent / DDQ / H2O; CH2Cl2 / 12 h / 20 °C
2: 87 percent / Dess-Martin periodinane / CH2Cl2 / 18 h / 20 °C
3: 87 percent / CrCl2 / tetrahydrofuran; dioxane / 16 h / 20 °C
4: 88 percent / BBr3 / CH2Cl2 / 1 h / -78 °C
5: copper(I) thiophene-2-carboxylate; Rb2CO3 / N,N-dimethyl-acetamide / 2 h / 90 °C
View Scheme
(12E)-(7S,9R,10S)-7-[(2E)-3-(carboallyloxy)prop-2-enyl]-4,9-dihydroxy-10-methyl-7,8,9,10,11,14-hexahydro-6-oxa-benzocyclodecen-5-one
320573-58-8

(12E)-(7S,9R,10S)-7-[(2E)-3-(carboallyloxy)prop-2-enyl]-4,9-dihydroxy-10-methyl-7,8,9,10,11,14-hexahydro-6-oxa-benzocyclodecen-5-one

(-)-salicylihalamide A
198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 92 percent / imidazole; DMAP / dimethylformamide / 10 h / 20 °C
2.1: 96 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran / 4 h / 20 °C
3.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
4.1: benzene / 6 h / 75 °C
5.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
5.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
6.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: 95 percent / imidazole / dimethylformamide
2.1: 97 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran
3.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
4.1: benzene / 6 h / 75 °C
5.1: t-BuLi / diethyl ether; tetrahydrofuran / 0.75 h / -78 °C
5.2: diethyl ether; tetrahydrofuran / -78 - 0 °C
5.3: HF*pyridine / pyridine; tetrahydrofuran / 48 h / 20 °C
View Scheme
(12E)-(7S,9R,10S)-4,9-bis-(tert-butyldimethylsilyloxy)-7-[(2E)-3-(carboallyloxy)prop-2-enyl]-10-methyl-7,8,9,10,11,14-hexahydro-6-oxa-benzocyclodecen-5-one
320573-59-9

(12E)-(7S,9R,10S)-4,9-bis-(tert-butyldimethylsilyloxy)-7-[(2E)-3-(carboallyloxy)prop-2-enyl]-10-methyl-7,8,9,10,11,14-hexahydro-6-oxa-benzocyclodecen-5-one

(-)-salicylihalamide A
198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 96 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran / 4 h / 20 °C
2.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
3.1: benzene / 6 h / 75 °C
4.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
4.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
5.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: 97 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran
2.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
3.1: benzene / 6 h / 75 °C
4.1: t-BuLi / diethyl ether; tetrahydrofuran / 0.75 h / -78 °C
4.2: diethyl ether; tetrahydrofuran / -78 - 0 °C
4.3: HF*pyridine / pyridine; tetrahydrofuran / 48 h / 20 °C
View Scheme
2,2-dimethyl-5-trifluoromethylsulfonyloxy-4H-(1,3)benzodioxin-4-one
164014-40-8

2,2-dimethyl-5-trifluoromethylsulfonyloxy-4H-(1,3)benzodioxin-4-one

Me2CuLi

Me2CuLi

(-)-salicylihalamide A
198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 16 steps
1.1: 1.3 g / LiCl; Pd2(dba)3; tri-(2-furyl)phosphine / 1-methyl-pyrrolidin-2-one / 48 h / 20 °C
2.1: EtMgBr / tetrahydrofuran / 0.25 h / 20 °C
2.2: 90 percent / tetrahydrofuran / 7.5 h / 20 - 60 °C
3.1: 98 percent / K2CO3 / acetone / 40 h / 20 °C
4.1: 96 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 1 h / 20 °C
5.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
6.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
7.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
8.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
9.1: NaH / tetrahydrofuran / 1 h / 0 °C
10.1: 64 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
11.1: Ba(OH)2*8H2O / tetrahydrofuran / 20 °C
12.1: imidazole; DMAP / dimethylformamide / 20 °C
13.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
14.1: benzene / 6 h / 75 °C
15.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
15.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
16.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 16 steps
1.1: 1.3 g / LiCl; Pd2(dba)3; tri-(2-furyl)phosphine / 1-methyl-pyrrolidin-2-one / 48 h / 20 °C
2.1: EtMgBr / tetrahydrofuran / 0.25 h / 20 °C
2.2: 90 percent / tetrahydrofuran / 7.5 h / 20 - 60 °C
3.1: 98 percent / K2CO3 / acetone / 40 h / 20 °C
4.1: 96 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 1 h / 20 °C
5.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
6.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
7.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
8.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
9.1: 93 percent / NaH / tetrahydrofuran / 1 h / 0 °C
10.1: 81 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
11.1: 92 percent / imidazole; DMAP / dimethylformamide / 10 h / 20 °C
12.1: 96 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran / 4 h / 20 °C
13.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
14.1: benzene / 6 h / 75 °C
15.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
15.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
16.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
2,2-dimethyl-5-(2-propenyl)-4H-1,3-benzodioxin-4-one
204846-40-2

2,2-dimethyl-5-(2-propenyl)-4H-1,3-benzodioxin-4-one

(-)-salicylihalamide A
198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1.1: EtMgBr / tetrahydrofuran / 0.25 h / 20 °C
1.2: 90 percent / tetrahydrofuran / 7.5 h / 20 - 60 °C
2.1: 98 percent / K2CO3 / acetone / 40 h / 20 °C
3.1: 96 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 1 h / 20 °C
4.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
5.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
6.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
7.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
8.1: NaH / tetrahydrofuran / 1 h / 0 °C
9.1: 64 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
10.1: Ba(OH)2*8H2O / tetrahydrofuran / 20 °C
11.1: imidazole; DMAP / dimethylformamide / 20 °C
12.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
13.1: benzene / 6 h / 75 °C
14.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
14.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
15.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 15 steps
1.1: EtMgBr / tetrahydrofuran / 0.25 h / 20 °C
1.2: 90 percent / tetrahydrofuran / 7.5 h / 20 - 60 °C
2.1: 98 percent / K2CO3 / acetone / 40 h / 20 °C
3.1: 96 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 1 h / 20 °C
4.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
5.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
6.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
7.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
8.1: 93 percent / NaH / tetrahydrofuran / 1 h / 0 °C
9.1: 81 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
10.1: 92 percent / imidazole; DMAP / dimethylformamide / 10 h / 20 °C
11.1: 96 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran / 4 h / 20 °C
12.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
13.1: benzene / 6 h / 75 °C
14.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
14.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
15.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
2-methoxy-6-(prop-2-enyl)benzoic acid allyl ester
325172-48-3

2-methoxy-6-(prop-2-enyl)benzoic acid allyl ester

(-)-salicylihalamide A
198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: 96 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 1 h / 20 °C
2.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
3.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
4.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
5.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
6.1: NaH / tetrahydrofuran / 1 h / 0 °C
7.1: 64 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
8.1: Ba(OH)2*8H2O / tetrahydrofuran / 20 °C
9.1: imidazole; DMAP / dimethylformamide / 20 °C
10.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
11.1: benzene / 6 h / 75 °C
12.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
12.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
13.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 13 steps
1.1: 96 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 1 h / 20 °C
2.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
3.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
4.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
5.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
6.1: 93 percent / NaH / tetrahydrofuran / 1 h / 0 °C
7.1: 81 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
8.1: 92 percent / imidazole; DMAP / dimethylformamide / 10 h / 20 °C
9.1: 96 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran / 4 h / 20 °C
10.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
11.1: benzene / 6 h / 75 °C
12.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
12.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
13.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
2-hydroxy-6-(prop-2-enyl)benzoic acid allyl ester
325172-47-2

2-hydroxy-6-(prop-2-enyl)benzoic acid allyl ester

(-)-salicylihalamide A
198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1.1: 98 percent / K2CO3 / acetone / 40 h / 20 °C
2.1: 96 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 1 h / 20 °C
3.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
4.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
5.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
6.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
7.1: NaH / tetrahydrofuran / 1 h / 0 °C
8.1: 64 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
9.1: Ba(OH)2*8H2O / tetrahydrofuran / 20 °C
10.1: imidazole; DMAP / dimethylformamide / 20 °C
11.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
12.1: benzene / 6 h / 75 °C
13.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
13.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
14.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 14 steps
1.1: 98 percent / K2CO3 / acetone / 40 h / 20 °C
2.1: 96 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 1 h / 20 °C
3.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
4.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
5.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
6.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
7.1: 93 percent / NaH / tetrahydrofuran / 1 h / 0 °C
8.1: 81 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
9.1: 92 percent / imidazole; DMAP / dimethylformamide / 10 h / 20 °C
10.1: 96 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran / 4 h / 20 °C
11.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
12.1: benzene / 6 h / 75 °C
13.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
13.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
14.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
(3S)-1-[(4-methoxyphenyl)methoxy]hex-5-en-3-ol
380909-94-4

(3S)-1-[(4-methoxyphenyl)methoxy]hex-5-en-3-ol

(-)-salicylihalamide A
198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 21 steps
1.1: 94 percent / imidazole; DMAP / dimethylformamide / 16 h / 20 °C
2.1: 21 g / OsO4; NMO / acetone; 2-methyl-propan-2-ol / 16 h / 0 - 20 °C
3.1: 18.0 g / NaIO4 / CH2Cl2 / 2 h / 20 °C
4.1: TiCl4; i-Pr2NEt / CH2Cl2 / 1 h / -78 °C
4.2: 92 percent / CH2Cl2 / 2 h / -78 °C
5.1: 91 percent / NaI; i-Pr2NEt / 1,2-dimethoxy-ethane / 12 h / Heating
6.1: 91 percent / LiEt3BH / tetrahydrofuran / 3 h / 20 °C
7.1: 91 percent / DMAP; Et3N / CH2Cl2 / 21 h / 20 - 35 °C
8.1: 92 percent / LiEt3BH / tetrahydrofuran / 18 h / 20 °C
9.1: 98 percent / TBAF / tetrahydrofuran / 12 h / 20 °C
10.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
11.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
12.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
13.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
14.1: NaH / tetrahydrofuran / 1 h / 0 °C
15.1: 64 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
16.1: Ba(OH)2*8H2O / tetrahydrofuran / 20 °C
17.1: imidazole; DMAP / dimethylformamide / 20 °C
18.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
19.1: benzene / 6 h / 75 °C
20.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
20.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
21.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 21 steps
1.1: 94 percent / imidazole; DMAP / dimethylformamide / 16 h / 20 °C
2.1: 21 g / OsO4; NMO / acetone; 2-methyl-propan-2-ol / 16 h / 0 - 20 °C
3.1: 18.0 g / NaIO4 / CH2Cl2 / 2 h / 20 °C
4.1: TiCl4; i-Pr2NEt / CH2Cl2 / 1 h / -78 °C
4.2: 92 percent / CH2Cl2 / 2 h / -78 °C
5.1: 91 percent / NaI; i-Pr2NEt / 1,2-dimethoxy-ethane / 12 h / Heating
6.1: 91 percent / LiEt3BH / tetrahydrofuran / 3 h / 20 °C
7.1: 91 percent / DMAP; Et3N / CH2Cl2 / 21 h / 20 - 35 °C
8.1: 92 percent / LiEt3BH / tetrahydrofuran / 18 h / 20 °C
9.1: 98 percent / TBAF / tetrahydrofuran / 12 h / 20 °C
10.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
11.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
12.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
13.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
14.1: 93 percent / NaH / tetrahydrofuran / 1 h / 0 °C
15.1: 81 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
16.1: 92 percent / imidazole; DMAP / dimethylformamide / 10 h / 20 °C
17.1: 96 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran / 4 h / 20 °C
18.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
19.1: benzene / 6 h / 75 °C
20.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
20.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
21.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
(S)-tert-butyl((1-((4-methoxybenzyl)oxy)hex-5-en-3-yl)oxy)dimethylsilane
380909-41-1

(S)-tert-butyl((1-((4-methoxybenzyl)oxy)hex-5-en-3-yl)oxy)dimethylsilane

(-)-salicylihalamide A
198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 20 steps
1.1: 21 g / OsO4; NMO / acetone; 2-methyl-propan-2-ol / 16 h / 0 - 20 °C
2.1: 18.0 g / NaIO4 / CH2Cl2 / 2 h / 20 °C
3.1: TiCl4; i-Pr2NEt / CH2Cl2 / 1 h / -78 °C
3.2: 92 percent / CH2Cl2 / 2 h / -78 °C
4.1: 91 percent / NaI; i-Pr2NEt / 1,2-dimethoxy-ethane / 12 h / Heating
5.1: 91 percent / LiEt3BH / tetrahydrofuran / 3 h / 20 °C
6.1: 91 percent / DMAP; Et3N / CH2Cl2 / 21 h / 20 - 35 °C
7.1: 92 percent / LiEt3BH / tetrahydrofuran / 18 h / 20 °C
8.1: 98 percent / TBAF / tetrahydrofuran / 12 h / 20 °C
9.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
10.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
11.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
12.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
13.1: NaH / tetrahydrofuran / 1 h / 0 °C
14.1: 64 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
15.1: Ba(OH)2*8H2O / tetrahydrofuran / 20 °C
16.1: imidazole; DMAP / dimethylformamide / 20 °C
17.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
18.1: benzene / 6 h / 75 °C
19.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
19.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
20.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 20 steps
1.1: 21 g / OsO4; NMO / acetone; 2-methyl-propan-2-ol / 16 h / 0 - 20 °C
2.1: 18.0 g / NaIO4 / CH2Cl2 / 2 h / 20 °C
3.1: TiCl4; i-Pr2NEt / CH2Cl2 / 1 h / -78 °C
3.2: 92 percent / CH2Cl2 / 2 h / -78 °C
4.1: 91 percent / NaI; i-Pr2NEt / 1,2-dimethoxy-ethane / 12 h / Heating
5.1: 91 percent / LiEt3BH / tetrahydrofuran / 3 h / 20 °C
6.1: 91 percent / DMAP; Et3N / CH2Cl2 / 21 h / 20 - 35 °C
7.1: 92 percent / LiEt3BH / tetrahydrofuran / 18 h / 20 °C
8.1: 98 percent / TBAF / tetrahydrofuran / 12 h / 20 °C
9.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
10.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
11.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
12.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
13.1: 93 percent / NaH / tetrahydrofuran / 1 h / 0 °C
14.1: 81 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
15.1: 92 percent / imidazole; DMAP / dimethylformamide / 10 h / 20 °C
16.1: 96 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran / 4 h / 20 °C
17.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
18.1: benzene / 6 h / 75 °C
19.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
19.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
20.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
(3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(4-methoxybenzyl)oxy]pentanal
398478-52-9

(3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(4-methoxybenzyl)oxy]pentanal

(-)-salicylihalamide A
198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 18 steps
1.1: TiCl4; i-Pr2NEt / CH2Cl2 / 1 h / -78 °C
1.2: 92 percent / CH2Cl2 / 2 h / -78 °C
2.1: 91 percent / NaI; i-Pr2NEt / 1,2-dimethoxy-ethane / 12 h / Heating
3.1: 91 percent / LiEt3BH / tetrahydrofuran / 3 h / 20 °C
4.1: 91 percent / DMAP; Et3N / CH2Cl2 / 21 h / 20 - 35 °C
5.1: 92 percent / LiEt3BH / tetrahydrofuran / 18 h / 20 °C
6.1: 98 percent / TBAF / tetrahydrofuran / 12 h / 20 °C
7.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
8.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
9.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
10.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
11.1: NaH / tetrahydrofuran / 1 h / 0 °C
12.1: 64 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
13.1: Ba(OH)2*8H2O / tetrahydrofuran / 20 °C
14.1: imidazole; DMAP / dimethylformamide / 20 °C
15.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
16.1: benzene / 6 h / 75 °C
17.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
17.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
18.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 18 steps
1.1: TiCl4; i-Pr2NEt / CH2Cl2 / 1 h / -78 °C
1.2: 92 percent / CH2Cl2 / 2 h / -78 °C
2.1: 91 percent / NaI; i-Pr2NEt / 1,2-dimethoxy-ethane / 12 h / Heating
3.1: 91 percent / LiEt3BH / tetrahydrofuran / 3 h / 20 °C
4.1: 91 percent / DMAP; Et3N / CH2Cl2 / 21 h / 20 - 35 °C
5.1: 92 percent / LiEt3BH / tetrahydrofuran / 18 h / 20 °C
6.1: 98 percent / TBAF / tetrahydrofuran / 12 h / 20 °C
7.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
8.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
9.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
10.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
11.1: 93 percent / NaH / tetrahydrofuran / 1 h / 0 °C
12.1: 81 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
13.1: 92 percent / imidazole; DMAP / dimethylformamide / 10 h / 20 °C
14.1: 96 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran / 4 h / 20 °C
15.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
16.1: benzene / 6 h / 75 °C
17.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
17.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
18.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
(3R,5R,6S)-1-(4-methoxybenzyloxy)-5-(methoxymethoxy)-6-methylnon-8-en-3-ol
398478-56-3

(3R,5R,6S)-1-(4-methoxybenzyloxy)-5-(methoxymethoxy)-6-methylnon-8-en-3-ol

(-)-salicylihalamide A
198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
2.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
3.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
4.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
5.1: NaH / tetrahydrofuran / 1 h / 0 °C
6.1: 64 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
7.1: Ba(OH)2*8H2O / tetrahydrofuran / 20 °C
8.1: imidazole; DMAP / dimethylformamide / 20 °C
9.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
10.1: benzene / 6 h / 75 °C
11.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
11.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
12.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 12 steps
1.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
2.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
3.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
4.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
5.1: 93 percent / NaH / tetrahydrofuran / 1 h / 0 °C
6.1: 81 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
7.1: 92 percent / imidazole; DMAP / dimethylformamide / 10 h / 20 °C
8.1: 96 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran / 4 h / 20 °C
9.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
10.1: benzene / 6 h / 75 °C
11.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
11.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
12.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
4-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-hexane-1,2-diol
398478-22-3

4-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-hexane-1,2-diol

(-)-salicylihalamide A
198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 19 steps
1.1: 18.0 g / NaIO4 / CH2Cl2 / 2 h / 20 °C
2.1: TiCl4; i-Pr2NEt / CH2Cl2 / 1 h / -78 °C
2.2: 92 percent / CH2Cl2 / 2 h / -78 °C
3.1: 91 percent / NaI; i-Pr2NEt / 1,2-dimethoxy-ethane / 12 h / Heating
4.1: 91 percent / LiEt3BH / tetrahydrofuran / 3 h / 20 °C
5.1: 91 percent / DMAP; Et3N / CH2Cl2 / 21 h / 20 - 35 °C
6.1: 92 percent / LiEt3BH / tetrahydrofuran / 18 h / 20 °C
7.1: 98 percent / TBAF / tetrahydrofuran / 12 h / 20 °C
8.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
9.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
10.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
11.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
12.1: NaH / tetrahydrofuran / 1 h / 0 °C
13.1: 64 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
14.1: Ba(OH)2*8H2O / tetrahydrofuran / 20 °C
15.1: imidazole; DMAP / dimethylformamide / 20 °C
16.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
17.1: benzene / 6 h / 75 °C
18.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
18.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
19.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 19 steps
1.1: 18.0 g / NaIO4 / CH2Cl2 / 2 h / 20 °C
2.1: TiCl4; i-Pr2NEt / CH2Cl2 / 1 h / -78 °C
2.2: 92 percent / CH2Cl2 / 2 h / -78 °C
3.1: 91 percent / NaI; i-Pr2NEt / 1,2-dimethoxy-ethane / 12 h / Heating
4.1: 91 percent / LiEt3BH / tetrahydrofuran / 3 h / 20 °C
5.1: 91 percent / DMAP; Et3N / CH2Cl2 / 21 h / 20 - 35 °C
6.1: 92 percent / LiEt3BH / tetrahydrofuran / 18 h / 20 °C
7.1: 98 percent / TBAF / tetrahydrofuran / 12 h / 20 °C
8.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
9.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
10.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
11.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
12.1: 93 percent / NaH / tetrahydrofuran / 1 h / 0 °C
13.1: 81 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
14.1: 92 percent / imidazole; DMAP / dimethylformamide / 10 h / 20 °C
15.1: 96 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran / 4 h / 20 °C
16.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
17.1: benzene / 6 h / 75 °C
18.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
18.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
19.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
(4S,5R,7R)-6-(tert-butyldimethylsilyloxy)-9-(4-methoxybenzyloxy)-5-methoxymethoxy-4-methylnon-1-ene
398478-55-2

(4S,5R,7R)-6-(tert-butyldimethylsilyloxy)-9-(4-methoxybenzyloxy)-5-methoxymethoxy-4-methylnon-1-ene

(-)-salicylihalamide A
198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: 98 percent / TBAF / tetrahydrofuran / 12 h / 20 °C
2.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
3.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
4.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
5.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
6.1: NaH / tetrahydrofuran / 1 h / 0 °C
7.1: 64 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
8.1: Ba(OH)2*8H2O / tetrahydrofuran / 20 °C
9.1: imidazole; DMAP / dimethylformamide / 20 °C
10.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
11.1: benzene / 6 h / 75 °C
12.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
12.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
13.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 13 steps
1.1: 98 percent / TBAF / tetrahydrofuran / 12 h / 20 °C
2.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
3.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
4.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
5.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
6.1: 93 percent / NaH / tetrahydrofuran / 1 h / 0 °C
7.1: 81 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
8.1: 92 percent / imidazole; DMAP / dimethylformamide / 10 h / 20 °C
9.1: 96 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran / 4 h / 20 °C
10.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
11.1: benzene / 6 h / 75 °C
12.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
12.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
13.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
(2R,3R,5R)-5-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-3-methoxymethoxy-2-(prop-2-enyl)heptan-1-ol
398478-23-4

(2R,3R,5R)-5-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-3-methoxymethoxy-2-(prop-2-enyl)heptan-1-ol

(-)-salicylihalamide A
198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1.1: 91 percent / DMAP; Et3N / CH2Cl2 / 21 h / 20 - 35 °C
2.1: 92 percent / LiEt3BH / tetrahydrofuran / 18 h / 20 °C
3.1: 98 percent / TBAF / tetrahydrofuran / 12 h / 20 °C
4.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
5.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
6.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
7.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
8.1: NaH / tetrahydrofuran / 1 h / 0 °C
9.1: 64 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
10.1: Ba(OH)2*8H2O / tetrahydrofuran / 20 °C
11.1: imidazole; DMAP / dimethylformamide / 20 °C
12.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
13.1: benzene / 6 h / 75 °C
14.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
14.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
15.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 15 steps
1.1: 91 percent / DMAP; Et3N / CH2Cl2 / 21 h / 20 - 35 °C
2.1: 92 percent / LiEt3BH / tetrahydrofuran / 18 h / 20 °C
3.1: 98 percent / TBAF / tetrahydrofuran / 12 h / 20 °C
4.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
5.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
6.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
7.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
8.1: 93 percent / NaH / tetrahydrofuran / 1 h / 0 °C
9.1: 81 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
10.1: 92 percent / imidazole; DMAP / dimethylformamide / 10 h / 20 °C
11.1: 96 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran / 4 h / 20 °C
12.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
13.1: benzene / 6 h / 75 °C
14.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
14.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
15.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
2-methoxy-6-(prop-2-enyl)benzoic acid (1S,3R,4S)-1-[2-(4-methoxybenzyloxy)ethyl]-3-methoxymethoxy-4-methylhept-6-enyl ester
398478-57-4

2-methoxy-6-(prop-2-enyl)benzoic acid (1S,3R,4S)-1-[2-(4-methoxybenzyloxy)ethyl]-3-methoxymethoxy-4-methylhept-6-enyl ester

(-)-salicylihalamide A
198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
2.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
3.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
4.1: NaH / tetrahydrofuran / 1 h / 0 °C
5.1: 64 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
6.1: Ba(OH)2*8H2O / tetrahydrofuran / 20 °C
7.1: imidazole; DMAP / dimethylformamide / 20 °C
8.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
9.1: benzene / 6 h / 75 °C
10.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
10.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
11.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 11 steps
1.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
2.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
3.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
4.1: 93 percent / NaH / tetrahydrofuran / 1 h / 0 °C
5.1: 81 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
6.1: 92 percent / imidazole; DMAP / dimethylformamide / 10 h / 20 °C
7.1: 96 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran / 4 h / 20 °C
8.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
9.1: benzene / 6 h / 75 °C
10.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
10.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
11.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
p-toluenesulfonic acid (2R,3R,5R)-5-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-3-methoxymethoxy-2-(prop-2-enyl)heptyl ester
398478-24-5

p-toluenesulfonic acid (2R,3R,5R)-5-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-3-methoxymethoxy-2-(prop-2-enyl)heptyl ester

(-)-salicylihalamide A
198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1.1: 92 percent / LiEt3BH / tetrahydrofuran / 18 h / 20 °C
2.1: 98 percent / TBAF / tetrahydrofuran / 12 h / 20 °C
3.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
4.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
5.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
6.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
7.1: NaH / tetrahydrofuran / 1 h / 0 °C
8.1: 64 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
9.1: Ba(OH)2*8H2O / tetrahydrofuran / 20 °C
10.1: imidazole; DMAP / dimethylformamide / 20 °C
11.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
12.1: benzene / 6 h / 75 °C
13.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
13.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
14.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 14 steps
1.1: 92 percent / LiEt3BH / tetrahydrofuran / 18 h / 20 °C
2.1: 98 percent / TBAF / tetrahydrofuran / 12 h / 20 °C
3.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
4.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
5.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
6.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
7.1: 93 percent / NaH / tetrahydrofuran / 1 h / 0 °C
8.1: 81 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
9.1: 92 percent / imidazole; DMAP / dimethylformamide / 10 h / 20 °C
10.1: 96 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran / 4 h / 20 °C
11.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
12.1: benzene / 6 h / 75 °C
13.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
13.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
14.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
(2S)-N-[(2S,3R,5R)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-7-(4-methoxybenzyloxy)-2-(prop-2-enyl)heptanoyl]bornane-10,2-sultam

(2S)-N-[(2S,3R,5R)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-7-(4-methoxybenzyloxy)-2-(prop-2-enyl)heptanoyl]bornane-10,2-sultam

(-)-salicylihalamide A
198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 17 steps
1.1: 91 percent / NaI; i-Pr2NEt / 1,2-dimethoxy-ethane / 12 h / Heating
2.1: 91 percent / LiEt3BH / tetrahydrofuran / 3 h / 20 °C
3.1: 91 percent / DMAP; Et3N / CH2Cl2 / 21 h / 20 - 35 °C
4.1: 92 percent / LiEt3BH / tetrahydrofuran / 18 h / 20 °C
5.1: 98 percent / TBAF / tetrahydrofuran / 12 h / 20 °C
6.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
7.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
8.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
9.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
10.1: NaH / tetrahydrofuran / 1 h / 0 °C
11.1: 64 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
12.1: Ba(OH)2*8H2O / tetrahydrofuran / 20 °C
13.1: imidazole; DMAP / dimethylformamide / 20 °C
14.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
15.1: benzene / 6 h / 75 °C
16.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
16.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
17.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 17 steps
1.1: 91 percent / NaI; i-Pr2NEt / 1,2-dimethoxy-ethane / 12 h / Heating
2.1: 91 percent / LiEt3BH / tetrahydrofuran / 3 h / 20 °C
3.1: 91 percent / DMAP; Et3N / CH2Cl2 / 21 h / 20 - 35 °C
4.1: 92 percent / LiEt3BH / tetrahydrofuran / 18 h / 20 °C
5.1: 98 percent / TBAF / tetrahydrofuran / 12 h / 20 °C
6.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
7.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
8.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
9.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
10.1: 93 percent / NaH / tetrahydrofuran / 1 h / 0 °C
11.1: 81 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
12.1: 92 percent / imidazole; DMAP / dimethylformamide / 10 h / 20 °C
13.1: 96 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran / 4 h / 20 °C
14.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
15.1: benzene / 6 h / 75 °C
16.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
16.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
17.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
(2S)-N-[(2S,3R,5R)-5-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-3-methoxymethoxy-2-(prop-2-enyl)heptanoyl]bornane-10,2-sultam

(2S)-N-[(2S,3R,5R)-5-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-3-methoxymethoxy-2-(prop-2-enyl)heptanoyl]bornane-10,2-sultam

(-)-salicylihalamide A
198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 16 steps
1.1: 91 percent / LiEt3BH / tetrahydrofuran / 3 h / 20 °C
2.1: 91 percent / DMAP; Et3N / CH2Cl2 / 21 h / 20 - 35 °C
3.1: 92 percent / LiEt3BH / tetrahydrofuran / 18 h / 20 °C
4.1: 98 percent / TBAF / tetrahydrofuran / 12 h / 20 °C
5.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
6.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
7.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
8.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
9.1: NaH / tetrahydrofuran / 1 h / 0 °C
10.1: 64 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
11.1: Ba(OH)2*8H2O / tetrahydrofuran / 20 °C
12.1: imidazole; DMAP / dimethylformamide / 20 °C
13.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
14.1: benzene / 6 h / 75 °C
15.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
15.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
16.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 16 steps
1.1: 91 percent / LiEt3BH / tetrahydrofuran / 3 h / 20 °C
2.1: 91 percent / DMAP; Et3N / CH2Cl2 / 21 h / 20 - 35 °C
3.1: 92 percent / LiEt3BH / tetrahydrofuran / 18 h / 20 °C
4.1: 98 percent / TBAF / tetrahydrofuran / 12 h / 20 °C
5.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
6.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
7.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
8.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
9.1: 93 percent / NaH / tetrahydrofuran / 1 h / 0 °C
10.1: 81 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
11.1: 92 percent / imidazole; DMAP / dimethylformamide / 10 h / 20 °C
12.1: 96 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran / 4 h / 20 °C
13.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
14.1: benzene / 6 h / 75 °C
15.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
15.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
16.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
(E)-4-((E)-(7S,9R,10S)-4-Methoxy-9-methoxymethoxy-10-methyl-5-oxo-7,8,9,10,11,14-hexahydro-5H-6-oxa-benzocyclododecen-7-yl)-but-2-enoic acid allyl ester

(E)-4-((E)-(7S,9R,10S)-4-Methoxy-9-methoxymethoxy-10-methyl-5-oxo-7,8,9,10,11,14-hexahydro-5H-6-oxa-benzocyclododecen-7-yl)-but-2-enoic acid allyl ester

(-)-salicylihalamide A
198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 81 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
2.1: 92 percent / imidazole; DMAP / dimethylformamide / 10 h / 20 °C
3.1: 96 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran / 4 h / 20 °C
4.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
5.1: benzene / 6 h / 75 °C
6.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
6.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
7.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
(2Z,4Z)-Hepta-2,4-dienoic acid {(E)-3-[(E)-(7S,9R,10S)-4,9-bis-(tert-butyl-dimethyl-silanyloxy)-10-methyl-5-oxo-7,8,9,10,11,14-hexahydro-5H-6-oxa-benzocyclododecen-7-yl]-propenyl}-amide
398478-62-1

(2Z,4Z)-Hepta-2,4-dienoic acid {(E)-3-[(E)-(7S,9R,10S)-4,9-bis-(tert-butyl-dimethyl-silanyloxy)-10-methyl-5-oxo-7,8,9,10,11,14-hexahydro-5H-6-oxa-benzocyclododecen-7-yl]-propenyl}-amide

A

(-)-salicylihalamide A
198481-99-1

(-)-salicylihalamide A

B

(2Z,4E)-Hepta-2,4-dienoic acid [(E)-3-((E)-(7S,9R,10S)-4,9-dihydroxy-10-methyl-5-oxo-7,8,9,10,11,14-hexahydro-5H-6-oxa-benzocyclododecen-7-yl)-propenyl]-amide

(2Z,4E)-Hepta-2,4-dienoic acid [(E)-3-((E)-(7S,9R,10S)-4,9-dihydroxy-10-methyl-5-oxo-7,8,9,10,11,14-hexahydro-5H-6-oxa-benzocyclododecen-7-yl)-propenyl]-amide

Conditions
ConditionsYield
With pyridine; hydrogen fluoride In tetrahydrofuran at 20℃; for 48h; Title compound not separated from byproducts.;
(12E)-(7S,9R,10S)-4,9-bis-(tert-butyldimethylsilyloxy)-7-[(2E)-3-carboxyprop-2-enyl]-10-methyl-7,8,9,10,11,14-hexahydro-6-oxa-benzocyclodecen-5-one
320573-60-2

(12E)-(7S,9R,10S)-4,9-bis-(tert-butyldimethylsilyloxy)-7-[(2E)-3-carboxyprop-2-enyl]-10-methyl-7,8,9,10,11,14-hexahydro-6-oxa-benzocyclodecen-5-one

(-)-salicylihalamide A
198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: N,N-diisopropylethylamine / acetone / 0 - 20 °C
2: sodium azide / acetone; H2O / 0.5 h / 20 °C
3: toluene / 0.25 h / 110 °C
4: 21.6 mg / toluene / 0.17 h / Heating
5: 81 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran; benzene / 0.17 h / 0 °C
6: tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C
7: 2.6 mg / HF*py / tetrahydrofuran; pyridine / 48 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
2.1: benzene / 6 h / 75 °C
3.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
3.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
4.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
2.1: benzene / 6 h / 75 °C
3.1: t-BuLi / diethyl ether; tetrahydrofuran / 0.75 h / -78 °C
3.2: diethyl ether; tetrahydrofuran / -78 - 0 °C
3.3: HF*pyridine / pyridine; tetrahydrofuran / 48 h / 20 °C
View Scheme
(12E)-(7S,9R,10S)-7-[(2E)-4-azido-4-oxo-but-2-enyl]-4,9-bis-(tert-butyldimethylsilyloxy)-10-methyl-7,8,9,10,11,14-hexahydro-6-oxa-benzocyclodecen-5-one
350794-21-7

(12E)-(7S,9R,10S)-7-[(2E)-4-azido-4-oxo-but-2-enyl]-4,9-bis-(tert-butyldimethylsilyloxy)-10-methyl-7,8,9,10,11,14-hexahydro-6-oxa-benzocyclodecen-5-one

(-)-salicylihalamide A
198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: toluene / 0.25 h / 110 °C
2: 21.6 mg / toluene / 0.17 h / Heating
3: 81 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran; benzene / 0.17 h / 0 °C
4: tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C
5: 2.6 mg / HF*py / tetrahydrofuran; pyridine / 48 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: benzene / 6 h / 75 °C
2.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
2.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
3.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: benzene / 6 h / 75 °C
2.1: t-BuLi / diethyl ether; tetrahydrofuran / 0.75 h / -78 °C
2.2: diethyl ether; tetrahydrofuran / -78 - 0 °C
2.3: HF*pyridine / pyridine; tetrahydrofuran / 48 h / 20 °C
View Scheme
(E)-(7S,9R,10S)-4,9-Bis-(tert-butyl-dimethyl-silanyloxy)-7-((E)-3-isocyanato-allyl)-10-methyl-7,8,9,10,11,14-hexahydro-6-oxa-benzocyclododecen-5-one
320573-61-3

(E)-(7S,9R,10S)-4,9-Bis-(tert-butyl-dimethyl-silanyloxy)-7-((E)-3-isocyanato-allyl)-10-methyl-7,8,9,10,11,14-hexahydro-6-oxa-benzocyclododecen-5-one

(-)-salicylihalamide A
198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 21.6 mg / toluene / 0.17 h / Heating
2: 81 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran; benzene / 0.17 h / 0 °C
3: tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C
4: 2.6 mg / HF*py / tetrahydrofuran; pyridine / 48 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
1.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
2.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
C19H23IO4

C19H23IO4

(2Z,4Z)-hepta-2,4-dienoic acid amide
345319-65-5

(2Z,4Z)-hepta-2,4-dienoic acid amide

A

(-)-salicylihalamide A
198481-99-1

(-)-salicylihalamide A

B

salicylihalamide B

salicylihalamide B

Conditions
ConditionsYield
With rubidium carbonate; [2,2]bipyridinyl; copper(I) thiophene-2-carboxylate In N,N-dimethyl acetamide at 90℃; for 1h; Inert atmosphere; Darkness; degassed solvent;A 23%
B 26%
...Expand
ethyl (3RS)-3-hydroxy-6-[(4-methoxybenzyl)oxy]hexanoate

ethyl (3RS)-3-hydroxy-6-[(4-methoxybenzyl)oxy]hexanoate

(-)-salicylihalamide A
198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 18 steps
1.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 - 23 °C
2.1: 83 percent / DIBAL / CH2Cl2 / 2 h / -78 °C
3.1: N,N,N',N'-tetramethyl-1,2-ethanediamine; TMEDA / TiCl4 / CH2Cl2 / 0.33 h / 0 °C
3.2: 78 percent / CH2Cl2 / 1 h / 0 °C
4.1: 86 percent / N,N-diisopropylethylamine; Bu4NI / CH2Cl2 / 12 h / 0 - 23 °C
5.1: 80 percent / aq. NaBH4 / tetrahydrofuran / 12 h / 0 - 23 °C
6.1: 100 percent / pyridine / 5 h / 0 °C
7.1: 89 percent / NaI; 1,8-diazabicyclo[5.4.0]undec-7-ene / 1,2-dimethoxy-ethane / 3 h / Heating
8.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 12 h / 0 - 23 °C
8.2: 84 percent / aq. NaOH / [PdCl2(1,1'-bis(diphenylphosphanyl)ferrocene)] / 4 h / 40 °C
9.1: 100 percent / TBAF / tetrahydrofuran / 48 h / 0 °C
10.1: 72 percent / aq. LiOH / tetrahydrofuran; ethanol / 72 h / 70 °C
11.1: polystyrene-bound PPh3 / tetrahydrofuran / 0.25 h / 23 °C
11.2: 72 percent / DEAD / toluene / 24 h / 0 - 20 °C
12.1: 52 percent / 9-I-9-BBN / hexane; CH2Cl2 / 0.03 h
13.1: 60 percent / DMAP; imidazole / dimethylformamide / 96 h / 23 °C
14.1: 85 percent / (+/-)-camphorsulfonic acid / CH2Cl2; methanol / 1.5 h / 0 °C
15.1: 91 percent / 4-methylmorpholine N-oxide; tetra-n-propylammonium perruthenate; 4 Angstroem molecular sieves / CH2Cl2 / 1 h / 0 °C
16.1: DIBAL / hexane; tetrahydrofuran / 0.5 h / 0 °C
16.2: 61 percent / hexane; tetrahydrofuran / 14 h / 0 °C
17.1: 45 percent / pyridine; Ac2O / tetrahydrofuran / 72 h
18.1: 75 percent / HF*pyridine / tetrahydrofuran / 72 h / 23 °C
View Scheme
Multi-step reaction with 17 steps
1.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 - 23 °C
2.1: 83 percent / DIBAL / CH2Cl2 / 2 h / -78 °C
3.1: (-)-sparteine / TiCl4 / CH2Cl2 / 0.42 h / 0 °C
3.2: 68 percent / CH2Cl2 / 1 h / 0 °C
4.1: 82 percent / iPr2NEt; Bu4NI / CH2Cl2 / 72 h / 23 °C
5.1: 86 percent / aq. NaBH4 / tetrahydrofuran / 12 h / 0 - 23 °C
6.1: 95 percent / pyridine / 12 h / 23 °C
7.1: 95 percent / Et3BHLi / tetrahydrofuran / 12 h / 0 - 23 °C
8.1: 99 percent / TBAF / tetrahydrofuran / 15 h / 0 °C
9.1: 71 percent / diisopropylazodicarboxylate; PPh3 / toluene / 3 h / 23 °C
10.1: 75 percent / Grubbs catalyst / toluene / 2 h / 70 °C
11.1: 52 percent / 9-I-9-BBN / hexane; CH2Cl2 / 0.03 h
12.1: 60 percent / DMAP; imidazole / dimethylformamide / 96 h / 23 °C
13.1: 85 percent / (+/-)-camphorsulfonic acid / CH2Cl2; methanol / 1.5 h / 0 °C
14.1: 91 percent / 4-methylmorpholine N-oxide; tetra-n-propylammonium perruthenate; 4 Angstroem molecular sieves / CH2Cl2 / 1 h / 0 °C
15.1: DIBAL / hexane; tetrahydrofuran / 0.5 h / 0 °C
15.2: 61 percent / hexane; tetrahydrofuran / 14 h / 0 °C
16.1: 45 percent / pyridine; Ac2O / tetrahydrofuran / 72 h
17.1: 75 percent / HF*pyridine / tetrahydrofuran / 72 h / 23 °C
View Scheme
(3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-hexanal
825612-52-0

(3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-hexanal

(-)-salicylihalamide A
198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 16 steps
1.1: N,N,N',N'-tetramethyl-1,2-ethanediamine; TMEDA / TiCl4 / CH2Cl2 / 0.33 h / 0 °C
1.2: 78 percent / CH2Cl2 / 1 h / 0 °C
2.1: 86 percent / N,N-diisopropylethylamine; Bu4NI / CH2Cl2 / 12 h / 0 - 23 °C
3.1: 80 percent / aq. NaBH4 / tetrahydrofuran / 12 h / 0 - 23 °C
4.1: 100 percent / pyridine / 5 h / 0 °C
5.1: 89 percent / NaI; 1,8-diazabicyclo[5.4.0]undec-7-ene / 1,2-dimethoxy-ethane / 3 h / Heating
6.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 12 h / 0 - 23 °C
6.2: 84 percent / aq. NaOH / [PdCl2(1,1'-bis(diphenylphosphanyl)ferrocene)] / 4 h / 40 °C
7.1: 100 percent / TBAF / tetrahydrofuran / 48 h / 0 °C
8.1: 72 percent / aq. LiOH / tetrahydrofuran; ethanol / 72 h / 70 °C
9.1: polystyrene-bound PPh3 / tetrahydrofuran / 0.25 h / 23 °C
9.2: 72 percent / DEAD / toluene / 24 h / 0 - 20 °C
10.1: 52 percent / 9-I-9-BBN / hexane; CH2Cl2 / 0.03 h
11.1: 60 percent / DMAP; imidazole / dimethylformamide / 96 h / 23 °C
12.1: 85 percent / (+/-)-camphorsulfonic acid / CH2Cl2; methanol / 1.5 h / 0 °C
13.1: 91 percent / 4-methylmorpholine N-oxide; tetra-n-propylammonium perruthenate; 4 Angstroem molecular sieves / CH2Cl2 / 1 h / 0 °C
14.1: DIBAL / hexane; tetrahydrofuran / 0.5 h / 0 °C
14.2: 61 percent / hexane; tetrahydrofuran / 14 h / 0 °C
15.1: 45 percent / pyridine; Ac2O / tetrahydrofuran / 72 h
16.1: 75 percent / HF*pyridine / tetrahydrofuran / 72 h / 23 °C
View Scheme
Multi-step reaction with 15 steps
1.1: (-)-sparteine / TiCl4 / CH2Cl2 / 0.42 h / 0 °C
1.2: 68 percent / CH2Cl2 / 1 h / 0 °C
2.1: 82 percent / iPr2NEt; Bu4NI / CH2Cl2 / 72 h / 23 °C
3.1: 86 percent / aq. NaBH4 / tetrahydrofuran / 12 h / 0 - 23 °C
4.1: 95 percent / pyridine / 12 h / 23 °C
5.1: 95 percent / Et3BHLi / tetrahydrofuran / 12 h / 0 - 23 °C
6.1: 99 percent / TBAF / tetrahydrofuran / 15 h / 0 °C
7.1: 71 percent / diisopropylazodicarboxylate; PPh3 / toluene / 3 h / 23 °C
8.1: 75 percent / Grubbs catalyst / toluene / 2 h / 70 °C
9.1: 52 percent / 9-I-9-BBN / hexane; CH2Cl2 / 0.03 h
10.1: 60 percent / DMAP; imidazole / dimethylformamide / 96 h / 23 °C
11.1: 85 percent / (+/-)-camphorsulfonic acid / CH2Cl2; methanol / 1.5 h / 0 °C
12.1: 91 percent / 4-methylmorpholine N-oxide; tetra-n-propylammonium perruthenate; 4 Angstroem molecular sieves / CH2Cl2 / 1 h / 0 °C
13.1: DIBAL / hexane; tetrahydrofuran / 0.5 h / 0 °C
13.2: 61 percent / hexane; tetrahydrofuran / 14 h / 0 °C
14.1: 45 percent / pyridine; Ac2O / tetrahydrofuran / 72 h
15.1: 75 percent / HF*pyridine / tetrahydrofuran / 72 h / 23 °C
View Scheme

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