Total synthesis of cytotoxic marine macrolides: Callipeltoside A, aurisides A and B, and dolastatin 19

Abstract

Synthetic studies pertaining to a novel class of structurally related glycosidic 14-membered macrolides of marine origin are reported. The evolution of a versatile aldol-based strategy that culminated in the total syntheses of callipeltoside A and aurisides A and B is detailed. Using a combination of biogenetic considerations and conformational analysis, a revised stereochemical assignment for the related polyketide dolastatin 19 was proposed and validated by total synthesis. © 2008 IUPAC.