Asymmetric synthetic approach to a functionalized azabicyclo[3.3.1]nonane moiety of (+)-sarain A

Abstract

This paper describes our efforts toward the asymmetric synthesis of sarain A which led to efficient preparation of a functionalized azabicyclo[3.3.1]nonane moiety. The key to the synthesis relied on a base-catalyzed asymmetric Diels-Alder cycloaddition to establish multiple stereocenters of a highly substituted cyclohexenone unit and a facile intramolecular aza-Michael addition to form the desired bicyclic system.