Pure Appl. Chem., 2007, Vol. 79, No. 4, pp. 667-676
doi: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.
Keywords: aldol; anticancer; macrolides; natural products; spiroacetal; stereocontrolled synthesis.
*Pure Appl. Chem. 79, 467-823 (2007) pp. 467-823. An issue of reviews and research papers based on lectures presented at the 25th International Symposium on Chemistry of Natural Products (ISCNP-25) and 5th International Conference on Biodiversity (ICOB-5), held jointly in Kyoto, Japan, 23-28 July 2006, on the theme of natural products.
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