The chemistry of zerumbone. Part 3: Stereospecific creation of five stereogenic centers by double Sharpless oxidation

Abstract The Sharpless asymmetric epoxidation was applied to zerumbol 2 in order to introduce chirality into the readily available achiral sesquiterpene zerumbone 1 . Single bisepoxides (+)- 3 and (−)- 3 were obtained in nearly 100% enantiomeric purity, characterized as the unexpected all erythro configuration by X-ray analysis.