Organoaluminum-Promoted Cyclization of Olefinic Epoxides. a New and Stereoselective Approach to Cyclohexane Frameworks

Article abstract of DOI:10.1246/bcsj.70.707

A new, general synthetic method of six-membered carbocycles has been demonstrated, which involves the stereo-controlled cyclization of olefinic epoxides with methylaluminum bis(4-bromo-2,6-di-t-butylphenoxide) (MABR) via the epoxide rearrangement and subsequent intramolecular ene reaction with high stereoselectivity. This strategy is shown to be highly useful in the stereoselective synthesis of the basic skeleton of various terpenes.