Multi-step reaction with 14 steps
1.1: trifluorormethanesulfonic acid / dichloromethane; cyclohexane / 0.5 h / 20 °C / Inert atmosphere
2.1: diisobutylaluminium hydride / dichloromethane; hexane / 0.08 h / -78 °C / Inert atmosphere
3.1: L-(+)-diisopropyl tartrate; titanium(IV) isopropylate; tert.-butylhydroperoxide / dichloromethane; decane / -20 °C / Inert atmosphere; Molecular sieve
4.1: dimethyl sulfoxide; sulfur trioxide pyridine complex; triethylamine / dichloromethane / 1.5 h / 0 °C / Inert atmosphere
5.1: dichloromethane / 0.02 h / 0 °C / Inert atmosphere
6.1: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; tributylphosphine; formic acid; triethylamine / 1,4-dioxane / 9.5 h / 20 °C / Inert atmosphere
7.1: 2,6-dimethylpyridine / dichloromethane / 0.33 h / 0 °C / Inert atmosphere
8.1: diisobutylaluminium hydride / dichloromethane; hexane / 0.12 h / -78 °C / Inert atmosphere
9.1: D-(-)-diisopropyl tartrate; titanium(IV) isopropylate; tert.-butylhydroperoxide / dichloromethane; decane / 4 h / -20 °C / Inert atmosphere; Molecular sieve
10.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite; sodium chlorite / acetonitrile / 1.5 h / pH 7 / Inert atmosphere
11.1: diethyl ether / 0 °C / Inert atmosphere
12.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.77 h / 0 °C / pH 7 / Inert atmosphere
13.1: camphor-10-sulfonic acid / dichloromethane / 5 h / 20 °C / Inert atmosphere
14.1: sodium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 °C / Inert atmosphere
14.2: 1.5 h / 0 - 20 °C / Inert atmosphere
With
2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium hypochlorite; sodium chlorite; formic acid; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; L-(+)-diisopropyl tartrate; tributylphosphine; trifluorormethanesulfonic acid; camphor-10-sulfonic acid; sulfur trioxide pyridine complex; sodium hydride; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; 1,4-dioxane; diethyl ether; decane; hexane; dichloromethane; cyclohexane; acetonitrile; mineral oil;
3.1: |Sharpless Asymmetric Epoxidation / 4.1: |Parikh-Doering Oxidation / 5.1: |Horner-Wadsworth-Emmons Olefination / 9.1: |Sharpless Asymmetric Epoxidation;
DOI:10.1021/jo400260m