Multi-step reaction with 13 steps
1.1: potassium carbonate / acetonitrile / 20 °C / Reflux
2.1: 16 h / 200 °C / Inert atmosphere
3.1: potassium carbonate / acetone / 6 h / Reflux
4.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / 20 °C
4.2: 6 h / Reflux
5.1: pyridinium chlorochromate / dichloromethane / 5 h / 0 - 20 °C / Molecular sieve
6.1: dichloromethane / 18 h / 20 °C
7.1: diisobutylaluminium hydride / toluene / 4 h / 0 - 20 °C / Inert atmosphere
8.1: titanium(IV) isopropylate; tert.-butylhydroperoxide / dichloromethane; decane / 18 h / -25 °C / Molecular sieve
9.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 2 h / 20 °C
9.2: 3 h / 0 °C
9.3: 0.67 h / 0 - 20 °C
10.1: toluene-4-sulfonic acid / 0.5 h / 20 °C
11.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C
12.1: toluene-4-sulfonic acid; water / methanol / 12 h / Reflux
13.1: sodium periodate; water / methanol / 2 h / 0 °C
13.2: 1 h / 0 - 20 °C
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium periodate; water; hydrogen; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; 9-borabicyclo[3.3.1]nonane; pyridinium chlorochromate;
palladium 10% on activated carbon;
In
tetrahydrofuran; methanol; decane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
2.1: Claisen Rearrangement / 6.1: Wittig Reaction / 8.1: Sharpless Epoxidation;