Chemical predisposition in synthesis: application to the preparation of the pyrrolidine natural products, plakoridines A and B

Abstract

The pyrrolidine natural products, plakoridines A and B, as well as an array of unnatural analogues, have been prepared using a five-step synthetic sequence modelled on a biogenetic theory. The key transformation involves a ‘Mannich/Michael/internal-redox’ cascade, which proceeds in yields of 31–63%.