Synthesis and Rearrangement Control of Substituted Benzobicycloheptane Aziridines

Abstract

A general synthesis of various substituted benzonorbornene derivatives is described. Benzenesulfonyl aziridines of these compounds were prepared and their acetolysis was studied. The influence of various substitution patterns on the direction of the aziridine rearrangement is discussed and it is shown that the rearrangements may be used as a convenient approach to the synthesis of ring B bridged diterpene alkaloids. Considerable general synthetic utility of these techniques is anticipated.