Studies toward a synthesis of (–)-secu'amamine A

Abstract

The Securinega alkaloids are characterized by their tetracyclic chemical backbone, butenolide moiety, and azabicyclo[3.2.1]octane ring system.1 Further study of the Securinega alkaloids has revealed such additional qualities as antimalarial,3 antibacterial,4 and cytotoxic.5 In addition to possessing the valuable biological activities of the Securinega alkaloids, the structure of (–)-secu'amamine A is appealing for its fused tetracyclic ring system consisting of an indolizidine ring (inherently bicyclic), a cyclohexene ring, and an α,β-unsaturated γ-lactone ring. To date only two total syntheses of (–)-secu’amamine A have been reported, both of which are linear syntheses. Here we proposed two different pathways which would allow for the convergent synthesis of (–)-secu'amamine A.