A stereoselective construction of a bicyclo[m.n.1] ring system from enol-lactones

Abstract

A stereoselective one-pot transformation of simple enol-lactone derivatives into the corresponding more complex compounds having the bicyclo[m.n.1] ring system was investigated. Under improved reduction conditions using DIBAL-H, the enol-lactones efficiently provided the bicyclo[m.n.1] derivatives via tandem reduction of the lactone moiety, aldol reaction and subsequent reduction of the resulting carbonyl functionality.