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Pure Appl. Chem., 2008, Vol. 80, No. 8, pp. 1773-1782

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

Ian Paterson and Alison D. Findlay

University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, UK

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.