Chemistry inspired by marine toxins I. Synthesis and functionalization of the ABCD domain of azaspiracid ; II. Ketene animal phosphates, dienes and organometallic couplings

Abstract

Discussed herein is the evolution of the strategies for the synthesis of the ABCD ring system of the novel marine toxin azaspiracid-1. Additionally, the methods utilized for the attachment of the C1-C4 side chain, the E-chain, and the FGHI domain are described. All of these efforts ultimately produced the first synthesis of the C5-C40 carbon chain of azaspiracid in enantiomencally pure form. Also described is the development of the methodology for the use of ketene aminal phosphates in synthesis. This is explored through their synthesis and further functionalization by organometallic chemistry.