An aldol-based synthesis of (+)-peloruside a, a potent microtubule stabilizing agent.
A convergent synthesis of the marine natural product (+)-peloruside has been reported. This target has been assembled through the successive application of two methyl ketone boron aldol addition reactions to the latent C(7)-C(11) dialdehyde synthon. This approach afforded a 22-step synthesis of this natural product. The influence of resident stereocenters on aldol reaction diastereoselection has been examined in detail.
Evans
David A
DA
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA. evans@chemistry.harvard.edu
Welch
Dennie S
DS
Speed
Alexander W H
AW
Moniz
George A
GA
Reichelt
Andreas
A
Ho
Stephen
S
D000438:Alcohols; D000447:Aldehydes; D000818:Animals; D001688:Biological Products / Q000138:chemical synthesis; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis*; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism; D050257:Tubulin Modulators / Q000138:chemical synthesis
D000438:Alcohols; D000447:Aldehydes; D001688:Biological Products; D019086:Bridged Bicyclo Compounds, Heterocyclic; D007783:Lactones; D050257:Tubulin Modulators; C414085:peloruside A