Pure Appl. Chem., 2005, Vol. 77, No. 1, pp. 103-117
doi:10.1351/pac200577010103
Approaches to the stereoselective total synthesis of biologically active natural products*
Anne Baron, Matthew Ball, Benjamin Bradshaw, Sam Donnelly, Olivier Germay, Pilar C. Oller, Naresh Kumar, Nathaniel Martin, Matthew O’Brien, Hiroki Omori, Christopher Moore, and Eric J. Thomas‡
Department of Chemistry, University of Manchester, Manchester, M13 9PL, UK
Abstract:
Total syntheses of epothilone B and pamamycin 607, which feature reactions between functionalized allylstannanes and aldehydes to introduce a (Z)-trisubstituted double-bond and remote stereocenters stereoselectively, are discussed. Recent work concerned with carrying out this chemistry without the use of allylstannanes as starting materials and progress toward a total synthesis of bryostatins are also presented.
Keywords: allylmetal; bryostatin syntthesis; epothilone synthesis; organobismuth; organostannane; pamamycin synthesis; remote stereocontrol; stereoselectivity.
*Paper based on a presentation at the 24th International Symposium on the Chemistry of Natural Products and the 4th International Congress on Biodiversity, held jointly in Delhi, India, 26-31 January 2004. Other presentations are published in this issue, pp. 1-344.