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Pure Appl. Chem., 2007, Vol. 79, No. 4, pp. 667-676

http://dx.doi.org/10.1351/pac200779040667

Progress toward a total synthesis of spirastrellolide A

Ian Paterson, Edward A. Anderson, Stephen M. Dalby, Jong Ho Lim, Olivier Loiseleur, Philip Maltas and Christian Moessner

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

Abstract: Progress toward a total synthesis of spirastrellolide A, a 38-membered marine macrolide, is reported. Syntheses of two diastereomers of the C1-C25 region, and an evolving Sharpless dihydroxylation strategy toward a C26-C40 fragment, are described. The syntheses exploit boron-mediated aldol chemistry to install key stereocenters, and feature late-stage thermodynamically controlled spiroacetalizations.