Synthesis of Optically Active Bicyclo[3.3.0]octane Skeleton Using Transannular Reaction

Abstract

Optically active 5-cyclooctene-1, 2-diol derivatives prepared by an enzymatic procedure have been converted into bicyclo[3.3.0]octane derivatives by transannular reaction with complete inversion of the stereogenic center linked to the leaving group. Formal synthesis of (+)-iridomyrmecin has been achieved starting from (S, S)-5-cyclooctene-1, 2-diol by using this process.