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Hebei Nengqian Chemical Import and Export Co., LTD

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Shanghai Upbio Tech Co.,Ltd

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Shandong Hanjiang Chemical Co., Ltd.

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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

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Hangzhou Dingyan Chem Co., Ltd

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Antimex Chemical Limied

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Henan Kanbei Chemical Co.,LTD

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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

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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

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Nanjing Raymon Biotech Co., Ltd.

1H-Cyclonona[1,2-c:5,6-c']difuran-1,3,6,8(4H)-tetrone,10-ethyl-5,9,10,11-tetrahydro-4-propyl-, (4S,10R)-Appearance:Off white to slight yellow solid Storage:Store in dry and cool condition Package:25kg or according to cutomer's demand Application:Chem

1H-Cyclonona[1,2-c:5,6-c']difuran-1,3,6,8(4H)-tetrone,10-ethyl-5,9,10,11-tetrahydro-4-propyl-, (4S,10R)-

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Synthetic route

: (1Z,5Z)-(R)-8-Ethyl-3-propyl-cyclonona-1,5-diene-1,2,5,6-tetracarboxylic acid

: 743-51-1
(+)-byssochlamic acid

Conditions

Conditions	Yield
With hydrogenchloride dehydrative cyclization;

: 5441-51-0
4-ethylcyclohexanone

: 743-51-1
(+)-byssochlamic acid

Conditions

Conditions	Yield
Multi-step reaction with 16 steps 1.1: 93 percent / NaH / benzene / 1.5 h / Heating 2.1: Br2 / diethyl ether / 2.17 h / 0 °C 3.1: 39 percent / methanol / 0 - 20 °C 4.1: 98 percent / porcine liver esterase; aq. Na2HPO4; aq. K2HPO4 / acetone / 3 h / 20 °C / pH 7 5.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C 5.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C 6.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C 7.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C 7.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h 8.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 9.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C 10.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 11.1: aq. HF / acetonitrile / 1.5 h / 20 °C 12.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 13.1: CH2Cl2 / Photolysis 14.1: aq. LiOH / dioxane / 1.5 h / 50 °C 15.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 16.1: aq. HCl View Scheme
Multi-step reaction with 16 steps 1.1: 93 percent / NaH / benzene / 1.5 h / Heating 2.1: Br2 / diethyl ether / 2.17 h / 0 °C 3.1: 39 percent / methanol / 0 - 20 °C 4.1: 98 percent / porcine liver esterase; aq. Na2HPO4; aq. K2HPO4 / acetone / 3 h / 20 °C / pH 7 5.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C 5.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C 6.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C 7.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C 7.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h 8.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 9.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C 10.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 11.1: aq. HF / acetonitrile / 1.5 h / 20 °C 12.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 13.1: CH2Cl2 / Photolysis 13.2: toluene / Heating 14.1: aq. LiOH / dioxane / 1.5 h / 50 °C 15.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 16.1: aq. HCl View Scheme

Yield

Multi-step reaction with 16 steps
1.1: 93 percent / NaH / benzene / 1.5 h / Heating
2.1: Br2 / diethyl ether / 2.17 h / 0 °C
3.1: 39 percent / methanol / 0 - 20 °C
4.1: 98 percent / porcine liver esterase; aq. Na2HPO4; aq. K2HPO4 / acetone / 3 h / 20 °C / pH 7
5.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C
5.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C
6.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C
7.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C
7.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h
8.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
9.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
10.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
11.1: aq. HF / acetonitrile / 1.5 h / 20 °C
12.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
13.1: CH2Cl2 / Photolysis
14.1: aq. LiOH / dioxane / 1.5 h / 50 °C
15.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
16.1: aq. HCl
View Scheme

Multi-step reaction with 16 steps
1.1: 93 percent / NaH / benzene / 1.5 h / Heating
2.1: Br2 / diethyl ether / 2.17 h / 0 °C
3.1: 39 percent / methanol / 0 - 20 °C
4.1: 98 percent / porcine liver esterase; aq. Na2HPO4; aq. K2HPO4 / acetone / 3 h / 20 °C / pH 7
5.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C
5.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C
6.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C
7.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C
7.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h
8.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
9.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
10.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
11.1: aq. HF / acetonitrile / 1.5 h / 20 °C
12.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
13.1: CH2Cl2 / Photolysis
13.2: toluene / Heating
14.1: aq. LiOH / dioxane / 1.5 h / 50 °C
15.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
16.1: aq. HCl
View Scheme

: 114862-60-1
methyl 5-ethyl-2-oxo-cyclohexancarboxylate

: 743-51-1
(+)-byssochlamic acid

Conditions

Conditions	Yield
Multi-step reaction with 15 steps 1.1: Br2 / diethyl ether / 2.17 h / 0 °C 2.1: 39 percent / methanol / 0 - 20 °C 3.1: 98 percent / porcine liver esterase; aq. Na2HPO4; aq. K2HPO4 / acetone / 3 h / 20 °C / pH 7 4.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C 4.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C 5.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C 6.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C 6.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h 7.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 8.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C 9.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 10.1: aq. HF / acetonitrile / 1.5 h / 20 °C 11.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 12.1: CH2Cl2 / Photolysis 13.1: aq. LiOH / dioxane / 1.5 h / 50 °C 14.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 15.1: aq. HCl View Scheme
Multi-step reaction with 15 steps 1.1: Br2 / diethyl ether / 2.17 h / 0 °C 2.1: 39 percent / methanol / 0 - 20 °C 3.1: 98 percent / porcine liver esterase; aq. Na2HPO4; aq. K2HPO4 / acetone / 3 h / 20 °C / pH 7 4.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C 4.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C 5.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C 6.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C 6.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h 7.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 8.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C 9.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 10.1: aq. HF / acetonitrile / 1.5 h / 20 °C 11.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 12.1: CH2Cl2 / Photolysis 12.2: toluene / Heating 13.1: aq. LiOH / dioxane / 1.5 h / 50 °C 14.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 15.1: aq. HCl View Scheme

Yield

Multi-step reaction with 15 steps
1.1: Br2 / diethyl ether / 2.17 h / 0 °C
2.1: 39 percent / methanol / 0 - 20 °C
3.1: 98 percent / porcine liver esterase; aq. Na2HPO4; aq. K2HPO4 / acetone / 3 h / 20 °C / pH 7
4.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C
4.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C
5.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C
6.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C
6.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h
7.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
8.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
9.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
10.1: aq. HF / acetonitrile / 1.5 h / 20 °C
11.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
12.1: CH2Cl2 / Photolysis
13.1: aq. LiOH / dioxane / 1.5 h / 50 °C
14.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
15.1: aq. HCl
View Scheme

Multi-step reaction with 15 steps
1.1: Br2 / diethyl ether / 2.17 h / 0 °C
2.1: 39 percent / methanol / 0 - 20 °C
3.1: 98 percent / porcine liver esterase; aq. Na2HPO4; aq. K2HPO4 / acetone / 3 h / 20 °C / pH 7
4.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C
4.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C
5.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C
6.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C
6.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h
7.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
8.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
9.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
10.1: aq. HF / acetonitrile / 1.5 h / 20 °C
11.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
12.1: CH2Cl2 / Photolysis
12.2: toluene / Heating
13.1: aq. LiOH / dioxane / 1.5 h / 50 °C
14.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
15.1: aq. HCl
View Scheme

: 144226-91-5
3-n-propylcyclobut-1-en-1,2-dicarboxylic acid

: 743-51-1
(+)-byssochlamic acid

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 59 percent / NaI; DIPEA / 1,2-dimethoxy-ethane / 4 h / 20 - 70 °C 2: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7 3: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 4: aq. HF / acetonitrile / 1.5 h / 20 °C 5: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 6: CH2Cl2 / Photolysis 7: aq. LiOH / dioxane / 1.5 h / 50 °C 8: KMnO4 / H2O; dioxane / 1 h / 40 °C 9: aq. HCl View Scheme
Multi-step reaction with 9 steps 1.1: 59 percent / NaI; DIPEA / 1,2-dimethoxy-ethane / 4 h / 20 - 70 °C 2.1: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7 3.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 4.1: aq. HF / acetonitrile / 1.5 h / 20 °C 5.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 6.1: CH2Cl2 / Photolysis 6.2: toluene / Heating 7.1: aq. LiOH / dioxane / 1.5 h / 50 °C 8.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 9.1: aq. HCl View Scheme

Yield

Multi-step reaction with 9 steps
1: 59 percent / NaI; DIPEA / 1,2-dimethoxy-ethane / 4 h / 20 - 70 °C
2: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7
3: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
4: aq. HF / acetonitrile / 1.5 h / 20 °C
5: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
6: CH2Cl2 / Photolysis
7: aq. LiOH / dioxane / 1.5 h / 50 °C
8: KMnO4 / H2O; dioxane / 1 h / 40 °C
9: aq. HCl
View Scheme

Multi-step reaction with 9 steps
1.1: 59 percent / NaI; DIPEA / 1,2-dimethoxy-ethane / 4 h / 20 - 70 °C
2.1: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7
3.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
4.1: aq. HF / acetonitrile / 1.5 h / 20 °C
5.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
6.1: CH2Cl2 / Photolysis
6.2: toluene / Heating
7.1: aq. LiOH / dioxane / 1.5 h / 50 °C
8.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
9.1: aq. HCl
View Scheme

: 144226-93-7
dimethyl 4-ethylcyclopenten-1,2-dicarboxylate

: 743-51-1
(+)-byssochlamic acid

Conditions

Conditions	Yield
Multi-step reaction with 13 steps 1.1: 98 percent / porcine liver esterase; aq. Na2HPO4; aq. K2HPO4 / acetone / 3 h / 20 °C / pH 7 2.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C 3.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C 4.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C 4.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h 5.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 6.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C 7.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 8.1: aq. HF / acetonitrile / 1.5 h / 20 °C 9.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 10.1: CH2Cl2 / Photolysis 11.1: aq. LiOH / dioxane / 1.5 h / 50 °C 12.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 13.1: aq. HCl View Scheme
Multi-step reaction with 13 steps 1.1: 98 percent / porcine liver esterase; aq. Na2HPO4; aq. K2HPO4 / acetone / 3 h / 20 °C / pH 7 2.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C 3.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C 4.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C 4.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h 5.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 6.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C 7.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 8.1: aq. HF / acetonitrile / 1.5 h / 20 °C 9.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 10.1: CH2Cl2 / Photolysis 10.2: toluene / Heating 11.1: aq. LiOH / dioxane / 1.5 h / 50 °C 12.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 13.1: aq. HCl View Scheme

Yield

Multi-step reaction with 13 steps
1.1: 98 percent / porcine liver esterase; aq. Na2HPO4; aq. K2HPO4 / acetone / 3 h / 20 °C / pH 7
2.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C
2.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C
3.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C
4.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C
4.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h
5.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
6.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
7.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
8.1: aq. HF / acetonitrile / 1.5 h / 20 °C
9.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
10.1: CH2Cl2 / Photolysis
11.1: aq. LiOH / dioxane / 1.5 h / 50 °C
12.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
13.1: aq. HCl
View Scheme

Multi-step reaction with 13 steps
1.1: 98 percent / porcine liver esterase; aq. Na2HPO4; aq. K2HPO4 / acetone / 3 h / 20 °C / pH 7
2.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C
2.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C
3.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C
4.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C
4.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h
5.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
6.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
7.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
8.1: aq. HF / acetonitrile / 1.5 h / 20 °C
9.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
10.1: CH2Cl2 / Photolysis
10.2: toluene / Heating
11.1: aq. LiOH / dioxane / 1.5 h / 50 °C
12.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
13.1: aq. HCl
View Scheme

: 144226-90-4
dimethyl 3-n-propylcyclobut-1-en-1,2-dicarboxylate

: 743-51-1
(+)-byssochlamic acid

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1: 72 percent / aq. LiOH / tetrahydrofuran / 1 h / 0 °C 2: 59 percent / NaI; DIPEA / 1,2-dimethoxy-ethane / 4 h / 20 - 70 °C 3: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7 4: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 5: aq. HF / acetonitrile / 1.5 h / 20 °C 6: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 7: CH2Cl2 / Photolysis 8: aq. LiOH / dioxane / 1.5 h / 50 °C 9: KMnO4 / H2O; dioxane / 1 h / 40 °C 10: aq. HCl View Scheme
Multi-step reaction with 10 steps 1.1: 72 percent / aq. LiOH / tetrahydrofuran / 1 h / 0 °C 2.1: 59 percent / NaI; DIPEA / 1,2-dimethoxy-ethane / 4 h / 20 - 70 °C 3.1: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7 4.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 5.1: aq. HF / acetonitrile / 1.5 h / 20 °C 6.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 7.1: CH2Cl2 / Photolysis 7.2: toluene / Heating 8.1: aq. LiOH / dioxane / 1.5 h / 50 °C 9.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 10.1: aq. HCl View Scheme

Yield

Multi-step reaction with 10 steps
1: 72 percent / aq. LiOH / tetrahydrofuran / 1 h / 0 °C
2: 59 percent / NaI; DIPEA / 1,2-dimethoxy-ethane / 4 h / 20 - 70 °C
3: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7
4: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
5: aq. HF / acetonitrile / 1.5 h / 20 °C
6: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
7: CH2Cl2 / Photolysis
8: aq. LiOH / dioxane / 1.5 h / 50 °C
9: KMnO4 / H2O; dioxane / 1 h / 40 °C
10: aq. HCl
View Scheme

Multi-step reaction with 10 steps
1.1: 72 percent / aq. LiOH / tetrahydrofuran / 1 h / 0 °C
2.1: 59 percent / NaI; DIPEA / 1,2-dimethoxy-ethane / 4 h / 20 - 70 °C
3.1: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7
4.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
5.1: aq. HF / acetonitrile / 1.5 h / 20 °C
6.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
7.1: CH2Cl2 / Photolysis
7.2: toluene / Heating
8.1: aq. LiOH / dioxane / 1.5 h / 50 °C
9.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
10.1: aq. HCl
View Scheme

: 144226-92-6
1,3-Dibromo-5-ethyl-2-oxo-cyclohexanecarboxylic acid methyl ester

: 743-51-1
(+)-byssochlamic acid

Conditions

Conditions	Yield
Multi-step reaction with 14 steps 1.1: 39 percent / methanol / 0 - 20 °C 2.1: 98 percent / porcine liver esterase; aq. Na2HPO4; aq. K2HPO4 / acetone / 3 h / 20 °C / pH 7 3.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C 3.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C 4.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C 5.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C 5.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h 6.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 7.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C 8.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 9.1: aq. HF / acetonitrile / 1.5 h / 20 °C 10.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 11.1: CH2Cl2 / Photolysis 12.1: aq. LiOH / dioxane / 1.5 h / 50 °C 13.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 14.1: aq. HCl View Scheme
Multi-step reaction with 14 steps 1.1: 39 percent / methanol / 0 - 20 °C 2.1: 98 percent / porcine liver esterase; aq. Na2HPO4; aq. K2HPO4 / acetone / 3 h / 20 °C / pH 7 3.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C 3.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C 4.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C 5.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C 5.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h 6.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 7.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C 8.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 9.1: aq. HF / acetonitrile / 1.5 h / 20 °C 10.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 11.1: CH2Cl2 / Photolysis 11.2: toluene / Heating 12.1: aq. LiOH / dioxane / 1.5 h / 50 °C 13.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 14.1: aq. HCl View Scheme

Yield

Multi-step reaction with 14 steps
1.1: 39 percent / methanol / 0 - 20 °C
2.1: 98 percent / porcine liver esterase; aq. Na2HPO4; aq. K2HPO4 / acetone / 3 h / 20 °C / pH 7
3.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C
3.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C
4.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C
5.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C
5.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h
6.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
7.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
8.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
9.1: aq. HF / acetonitrile / 1.5 h / 20 °C
10.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
11.1: CH2Cl2 / Photolysis
12.1: aq. LiOH / dioxane / 1.5 h / 50 °C
13.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
14.1: aq. HCl
View Scheme

Multi-step reaction with 14 steps
1.1: 39 percent / methanol / 0 - 20 °C
2.1: 98 percent / porcine liver esterase; aq. Na2HPO4; aq. K2HPO4 / acetone / 3 h / 20 °C / pH 7
3.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C
3.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C
4.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C
5.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C
5.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h
6.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
7.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
8.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
9.1: aq. HF / acetonitrile / 1.5 h / 20 °C
10.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
11.1: CH2Cl2 / Photolysis
11.2: toluene / Heating
12.1: aq. LiOH / dioxane / 1.5 h / 50 °C
13.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
14.1: aq. HCl
View Scheme

: 1-Bromo-4-propyl-cyclobutane-1,2-dicarboxylic acid

: 743-51-1
(+)-byssochlamic acid

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1: diethyl ether / 1 h / 0 °C 2: 5.60 g / DBU / CHCl3 / 1 h / Heating 3: 72 percent / aq. LiOH / tetrahydrofuran / 1 h / 0 °C 4: 59 percent / NaI; DIPEA / 1,2-dimethoxy-ethane / 4 h / 20 - 70 °C 5: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7 6: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 7: aq. HF / acetonitrile / 1.5 h / 20 °C 8: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 9: CH2Cl2 / Photolysis 10: aq. LiOH / dioxane / 1.5 h / 50 °C 11: KMnO4 / H2O; dioxane / 1 h / 40 °C 12: aq. HCl View Scheme
Multi-step reaction with 12 steps 1.1: diethyl ether / 1 h / 0 °C 2.1: 5.60 g / DBU / CHCl3 / 1 h / Heating 3.1: 72 percent / aq. LiOH / tetrahydrofuran / 1 h / 0 °C 4.1: 59 percent / NaI; DIPEA / 1,2-dimethoxy-ethane / 4 h / 20 - 70 °C 5.1: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7 6.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 7.1: aq. HF / acetonitrile / 1.5 h / 20 °C 8.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 9.1: CH2Cl2 / Photolysis 9.2: toluene / Heating 10.1: aq. LiOH / dioxane / 1.5 h / 50 °C 11.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 12.1: aq. HCl View Scheme

Yield

Multi-step reaction with 12 steps
1: diethyl ether / 1 h / 0 °C
2: 5.60 g / DBU / CHCl3 / 1 h / Heating
3: 72 percent / aq. LiOH / tetrahydrofuran / 1 h / 0 °C
4: 59 percent / NaI; DIPEA / 1,2-dimethoxy-ethane / 4 h / 20 - 70 °C
5: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7
6: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
7: aq. HF / acetonitrile / 1.5 h / 20 °C
8: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
9: CH2Cl2 / Photolysis
10: aq. LiOH / dioxane / 1.5 h / 50 °C
11: KMnO4 / H2O; dioxane / 1 h / 40 °C
12: aq. HCl
View Scheme

Multi-step reaction with 12 steps
1.1: diethyl ether / 1 h / 0 °C
2.1: 5.60 g / DBU / CHCl3 / 1 h / Heating
3.1: 72 percent / aq. LiOH / tetrahydrofuran / 1 h / 0 °C
4.1: 59 percent / NaI; DIPEA / 1,2-dimethoxy-ethane / 4 h / 20 - 70 °C
5.1: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7
6.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
7.1: aq. HF / acetonitrile / 1.5 h / 20 °C
8.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
9.1: CH2Cl2 / Photolysis
9.2: toluene / Heating
10.1: aq. LiOH / dioxane / 1.5 h / 50 °C
11.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
12.1: aq. HCl
View Scheme

: 1-Bromo-4-propyl-cyclobutane-1,2-dicarboxylic acid dimethyl ester

: 743-51-1
(+)-byssochlamic acid

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1: 5.60 g / DBU / CHCl3 / 1 h / Heating 2: 72 percent / aq. LiOH / tetrahydrofuran / 1 h / 0 °C 3: 59 percent / NaI; DIPEA / 1,2-dimethoxy-ethane / 4 h / 20 - 70 °C 4: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7 5: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 6: aq. HF / acetonitrile / 1.5 h / 20 °C 7: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 8: CH2Cl2 / Photolysis 9: aq. LiOH / dioxane / 1.5 h / 50 °C 10: KMnO4 / H2O; dioxane / 1 h / 40 °C 11: aq. HCl View Scheme
Multi-step reaction with 11 steps 1.1: 5.60 g / DBU / CHCl3 / 1 h / Heating 2.1: 72 percent / aq. LiOH / tetrahydrofuran / 1 h / 0 °C 3.1: 59 percent / NaI; DIPEA / 1,2-dimethoxy-ethane / 4 h / 20 - 70 °C 4.1: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7 5.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 6.1: aq. HF / acetonitrile / 1.5 h / 20 °C 7.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 8.1: CH2Cl2 / Photolysis 8.2: toluene / Heating 9.1: aq. LiOH / dioxane / 1.5 h / 50 °C 10.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 11.1: aq. HCl View Scheme

Yield

Multi-step reaction with 11 steps
1: 5.60 g / DBU / CHCl3 / 1 h / Heating
2: 72 percent / aq. LiOH / tetrahydrofuran / 1 h / 0 °C
3: 59 percent / NaI; DIPEA / 1,2-dimethoxy-ethane / 4 h / 20 - 70 °C
4: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7
5: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
6: aq. HF / acetonitrile / 1.5 h / 20 °C
7: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
8: CH2Cl2 / Photolysis
9: aq. LiOH / dioxane / 1.5 h / 50 °C
10: KMnO4 / H2O; dioxane / 1 h / 40 °C
11: aq. HCl
View Scheme

Multi-step reaction with 11 steps
1.1: 5.60 g / DBU / CHCl3 / 1 h / Heating
2.1: 72 percent / aq. LiOH / tetrahydrofuran / 1 h / 0 °C
3.1: 59 percent / NaI; DIPEA / 1,2-dimethoxy-ethane / 4 h / 20 - 70 °C
4.1: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7
5.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
6.1: aq. HF / acetonitrile / 1.5 h / 20 °C
7.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
8.1: CH2Cl2 / Photolysis
8.2: toluene / Heating
9.1: aq. LiOH / dioxane / 1.5 h / 50 °C
10.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
11.1: aq. HCl
View Scheme

: 301670-57-5
methyl (4R)-4-ethyl-2-hydroxymethylcyclopent-1-encarboxylate

: 743-51-1
(+)-byssochlamic acid

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C 2.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C 2.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h 3.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 4.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C 5.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 6.1: aq. HF / acetonitrile / 1.5 h / 20 °C 7.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 8.1: CH2Cl2 / Photolysis 9.1: aq. LiOH / dioxane / 1.5 h / 50 °C 10.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 11.1: aq. HCl View Scheme
Multi-step reaction with 11 steps 1.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C 2.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C 2.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h 3.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 4.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C 5.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 6.1: aq. HF / acetonitrile / 1.5 h / 20 °C 7.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 8.1: CH2Cl2 / Photolysis 8.2: toluene / Heating 9.1: aq. LiOH / dioxane / 1.5 h / 50 °C 10.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 11.1: aq. HCl View Scheme

Yield

Multi-step reaction with 11 steps
1.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C
2.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C
2.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h
3.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
4.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
5.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
6.1: aq. HF / acetonitrile / 1.5 h / 20 °C
7.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
8.1: CH2Cl2 / Photolysis
9.1: aq. LiOH / dioxane / 1.5 h / 50 °C
10.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
11.1: aq. HCl
View Scheme

Multi-step reaction with 11 steps
1.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C
2.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C
2.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h
3.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
4.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
5.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
6.1: aq. HF / acetonitrile / 1.5 h / 20 °C
7.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
8.1: CH2Cl2 / Photolysis
8.2: toluene / Heating
9.1: aq. LiOH / dioxane / 1.5 h / 50 °C
10.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
11.1: aq. HCl
View Scheme

: 301670-38-2
(R)-4-Ethyl-cyclopent-1-ene-1,2-dicarboxylic acid monomethyl ester

: 743-51-1
(+)-byssochlamic acid

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C 1.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C 2.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C 3.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C 3.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h 4.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 5.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C 6.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 7.1: aq. HF / acetonitrile / 1.5 h / 20 °C 8.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 9.1: CH2Cl2 / Photolysis 10.1: aq. LiOH / dioxane / 1.5 h / 50 °C 11.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 12.1: aq. HCl View Scheme
Multi-step reaction with 12 steps 1.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C 1.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C 2.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C 3.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C 3.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h 4.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 5.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C 6.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 7.1: aq. HF / acetonitrile / 1.5 h / 20 °C 8.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 9.1: CH2Cl2 / Photolysis 9.2: toluene / Heating 10.1: aq. LiOH / dioxane / 1.5 h / 50 °C 11.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 12.1: aq. HCl View Scheme

Yield

Multi-step reaction with 12 steps
1.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C
1.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C
2.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C
3.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C
3.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h
4.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
5.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
6.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
7.1: aq. HF / acetonitrile / 1.5 h / 20 °C
8.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
9.1: CH2Cl2 / Photolysis
10.1: aq. LiOH / dioxane / 1.5 h / 50 °C
11.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
12.1: aq. HCl
View Scheme

Multi-step reaction with 12 steps
1.1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C
1.2: 89 percent / NaBH4 / H2O / 0.5 h / 0 °C
2.1: 93 percent / TsOH monohydrate / CH2Cl2 / 1 h / 20 °C
3.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C
3.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h
4.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
5.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
6.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
7.1: aq. HF / acetonitrile / 1.5 h / 20 °C
8.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
9.1: CH2Cl2 / Photolysis
9.2: toluene / Heating
10.1: aq. LiOH / dioxane / 1.5 h / 50 °C
11.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
12.1: aq. HCl
View Scheme

: 301670-67-7
3-propyl-cyclobut-1-ene-1,2-dicarboxylic acid 2-methylsulfanylmethyl ester

: 743-51-1
(+)-byssochlamic acid

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 2: aq. HF / acetonitrile / 1.5 h / 20 °C 3: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 4: CH2Cl2 / Photolysis 5: aq. LiOH / dioxane / 1.5 h / 50 °C 6: KMnO4 / H2O; dioxane / 1 h / 40 °C 7: aq. HCl View Scheme
Multi-step reaction with 7 steps 1.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 2.1: aq. HF / acetonitrile / 1.5 h / 20 °C 3.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 4.1: CH2Cl2 / Photolysis 4.2: toluene / Heating 5.1: aq. LiOH / dioxane / 1.5 h / 50 °C 6.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 7.1: aq. HCl View Scheme

: 301670-65-5
bis-(methylthio)methyl 3-n-propylcyclobut-1-en-1,2-dicarboxylate

: 743-51-1
(+)-byssochlamic acid

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7 2: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 3: aq. HF / acetonitrile / 1.5 h / 20 °C 4: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 5: CH2Cl2 / Photolysis 6: aq. LiOH / dioxane / 1.5 h / 50 °C 7: KMnO4 / H2O; dioxane / 1 h / 40 °C 8: aq. HCl View Scheme
Multi-step reaction with 8 steps 1.1: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7 2.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 3.1: aq. HF / acetonitrile / 1.5 h / 20 °C 4.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 5.1: CH2Cl2 / Photolysis 5.2: toluene / Heating 6.1: aq. LiOH / dioxane / 1.5 h / 50 °C 7.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 8.1: aq. HCl View Scheme

Yield

Multi-step reaction with 8 steps
1: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7
2: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
3: aq. HF / acetonitrile / 1.5 h / 20 °C
4: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
5: CH2Cl2 / Photolysis
6: aq. LiOH / dioxane / 1.5 h / 50 °C
7: KMnO4 / H2O; dioxane / 1 h / 40 °C
8: aq. HCl
View Scheme

Multi-step reaction with 8 steps
1.1: pig liver esteraze; Na2HPO4; K2HPO4 / acetone / 3 h / 20 °C / pH 7
2.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
3.1: aq. HF / acetonitrile / 1.5 h / 20 °C
4.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
5.1: CH2Cl2 / Photolysis
5.2: toluene / Heating
6.1: aq. LiOH / dioxane / 1.5 h / 50 °C
7.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
8.1: aq. HCl
View Scheme

: 301670-62-2
(4R)-4-ethyl-2-(tert-butyldimethylsilyloxy)methylcyclopent-1-enmethanol

: 743-51-1
(+)-byssochlamic acid

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 2: aq. HF / acetonitrile / 1.5 h / 20 °C 3: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 4: CH2Cl2 / Photolysis 5: aq. LiOH / dioxane / 1.5 h / 50 °C 6: KMnO4 / H2O; dioxane / 1 h / 40 °C 7: aq. HCl View Scheme
Multi-step reaction with 7 steps 1.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 2.1: aq. HF / acetonitrile / 1.5 h / 20 °C 3.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 4.1: CH2Cl2 / Photolysis 4.2: toluene / Heating 5.1: aq. LiOH / dioxane / 1.5 h / 50 °C 6.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 7.1: aq. HCl View Scheme

: 301670-59-7
(4S)-4-ethyl-2-(2-tetrahydropyranyloxy)methylcyclopent-1-enmethanol

: 743-51-1
(+)-byssochlamic acid

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 2: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C 3: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 4: aq. HF / acetonitrile / 1.5 h / 20 °C 5: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 6: CH2Cl2 / Photolysis 7: aq. LiOH / dioxane / 1.5 h / 50 °C 8: KMnO4 / H2O; dioxane / 1 h / 40 °C 9: aq. HCl View Scheme
Multi-step reaction with 9 steps 1.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 2.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C 3.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 4.1: aq. HF / acetonitrile / 1.5 h / 20 °C 5.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 6.1: CH2Cl2 / Photolysis 6.2: toluene / Heating 7.1: aq. LiOH / dioxane / 1.5 h / 50 °C 8.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 9.1: aq. HCl View Scheme

Yield

Multi-step reaction with 9 steps
1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
2: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
3: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
4: aq. HF / acetonitrile / 1.5 h / 20 °C
5: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
6: CH2Cl2 / Photolysis
7: aq. LiOH / dioxane / 1.5 h / 50 °C
8: KMnO4 / H2O; dioxane / 1 h / 40 °C
9: aq. HCl
View Scheme

Multi-step reaction with 9 steps
1.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
2.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
3.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
4.1: aq. HF / acetonitrile / 1.5 h / 20 °C
5.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
6.1: CH2Cl2 / Photolysis
6.2: toluene / Heating
7.1: aq. LiOH / dioxane / 1.5 h / 50 °C
8.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
9.1: aq. HCl
View Scheme

: 301670-58-6
methyl (4R)-4-ethyl-2-(2-tetrahydropyranyloxy)methylcyclopent-1-encarboxylate

: 743-51-1
(+)-byssochlamic acid

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C 1.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h 2.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 3.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C 4.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 5.1: aq. HF / acetonitrile / 1.5 h / 20 °C 6.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 7.1: CH2Cl2 / Photolysis 8.1: aq. LiOH / dioxane / 1.5 h / 50 °C 9.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 10.1: aq. HCl View Scheme
Multi-step reaction with 10 steps 1.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C 1.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h 2.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 3.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C 4.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 5.1: aq. HF / acetonitrile / 1.5 h / 20 °C 6.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 7.1: CH2Cl2 / Photolysis 7.2: toluene / Heating 8.1: aq. LiOH / dioxane / 1.5 h / 50 °C 9.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 10.1: aq. HCl View Scheme

Yield

Multi-step reaction with 10 steps
1.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C
1.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h
2.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
3.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
4.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
5.1: aq. HF / acetonitrile / 1.5 h / 20 °C
6.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
7.1: CH2Cl2 / Photolysis
8.1: aq. LiOH / dioxane / 1.5 h / 50 °C
9.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
10.1: aq. HCl
View Scheme

Multi-step reaction with 10 steps
1.1: DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C
1.2: 91 percent / Rochelle's salt / CH2Cl2 / 0.33 h
2.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
3.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C
4.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C
5.1: aq. HF / acetonitrile / 1.5 h / 20 °C
6.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating
7.1: CH2Cl2 / Photolysis
7.2: toluene / Heating
8.1: aq. LiOH / dioxane / 1.5 h / 50 °C
9.1: KMnO4 / H2O; dioxane / 1 h / 40 °C
10.1: aq. HCl
View Scheme

: 302350-30-7
(R)-14-Ethyl-6-propyl-3,10-dioxa-tricyclo[10.3.0.05,8]pentadeca-1(12),5(8)-diene-4,9-dione

: 743-51-1
(+)-byssochlamic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: CH2Cl2 / Photolysis 2: aq. LiOH / dioxane / 1.5 h / 50 °C 3: KMnO4 / H2O; dioxane / 1 h / 40 °C 4: aq. HCl View Scheme
Multi-step reaction with 4 steps 1.1: CH2Cl2 / Photolysis 1.2: toluene / Heating 2.1: aq. LiOH / dioxane / 1.5 h / 50 °C 3.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 4.1: aq. HCl View Scheme

: 302350-31-8
10-ethyl-4-propyl-4,5,8,9,10,11-hexahydro-1H-2,7-dioxa-dicyclopenta[a,e]cyclononene-3,6-dione

: 743-51-1
(+)-byssochlamic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: aq. LiOH / dioxane / 1.5 h / 50 °C 2: KMnO4 / H2O; dioxane / 1 h / 40 °C 3: aq. HCl View Scheme

: 301670-60-0
(4R)-1-(tert-butyldimethylsilyloxy)methyl-4-ethyl-2-(2-tetrahydropyranyloxy)methyl-cyclopent-1-ene

: 743-51-1
(+)-byssochlamic acid

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C 2: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 3: aq. HF / acetonitrile / 1.5 h / 20 °C 4: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 5: CH2Cl2 / Photolysis 6: aq. LiOH / dioxane / 1.5 h / 50 °C 7: KMnO4 / H2O; dioxane / 1 h / 40 °C 8: aq. HCl View Scheme
Multi-step reaction with 8 steps 1.1: 71 percent / MgBr2 / diethyl ether / 5 h / 20 °C 2.1: 60 percent / EDCl; DMAP / CH2Cl2 / 4 h / 20 °C 3.1: aq. HF / acetonitrile / 1.5 h / 20 °C 4.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 5.1: CH2Cl2 / Photolysis 5.2: toluene / Heating 6.1: aq. LiOH / dioxane / 1.5 h / 50 °C 7.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 8.1: aq. HCl View Scheme

: 3-Propyl-cyclobut-1-ene-1,2-dicarboxylic acid 1-((S)-4-ethyl-2-hydroxymethyl-cyclopent-1-enylmethyl) ester 2-methylsulfanylmethyl ester

: 743-51-1
(+)-byssochlamic acid

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 2: CH2Cl2 / Photolysis 3: aq. LiOH / dioxane / 1.5 h / 50 °C 4: KMnO4 / H2O; dioxane / 1 h / 40 °C 5: aq. HCl View Scheme
Multi-step reaction with 5 steps 1.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 2.1: CH2Cl2 / Photolysis 2.2: toluene / Heating 3.1: aq. LiOH / dioxane / 1.5 h / 50 °C 4.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 5.1: aq. HCl View Scheme

: (1Z,4Z)-(R)-7-Ethyl-5,9-bis-hydroxymethyl-2-propyl-cyclonona-4,9-diene-1,4-dicarboxylic acid

: 743-51-1
(+)-byssochlamic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: KMnO4 / H2O; dioxane / 1 h / 40 °C 2: aq. HCl View Scheme

: 301670-69-9
3-propyl-cyclobut-1-ene-1,2-dicarboxylic acid 1-[2-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethyl-cyclopent-1-enylmethyl] ester 2-methylsulfanylmethyl ester

: 743-51-1
(+)-byssochlamic acid

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: aq. HF / acetonitrile / 1.5 h / 20 °C 2: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 3: CH2Cl2 / Photolysis 4: aq. LiOH / dioxane / 1.5 h / 50 °C 5: KMnO4 / H2O; dioxane / 1 h / 40 °C 6: aq. HCl View Scheme
Multi-step reaction with 6 steps 1.1: aq. HF / acetonitrile / 1.5 h / 20 °C 2.1: 23.6 mg / DCC; DMAP*HCl / CHCl3 / 20 h / Heating 3.1: CH2Cl2 / Photolysis 3.2: toluene / Heating 4.1: aq. LiOH / dioxane / 1.5 h / 50 °C 5.1: KMnO4 / H2O; dioxane / 1 h / 40 °C 6.1: aq. HCl View Scheme

: C10H10O5

: 743-51-1
(+)-byssochlamic acid

Conditions

Conditions	Yield
With BfL10 ketosteroid isomerase obtained from E. coli Reagent/catalyst; Enzymatic reaction;

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