Approaches to the stereoselective total synthesis of biologically active natural products

Baron, Anne; Ball, Matthew; Bradshaw, Benjamin; Donnelly, Sam; Germay, Olivier; Oller, Pilar C.; Kumar, Naresh; Martin, Nathaniel; O’Brien, Matthew; Omori, Hiroki; Moore, Christopher; Thomas, Eric J.

doi:10.1351/pac200577010103

Pure Appl. Chem., 2005, Vol. 77, No. 1, pp. 103-117

http://dx.doi.org/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.