An aldol-based synthesis of (+)-peloruside a, a potent microtubule stabilizing agent

David A Evans; Dennie S Welch; Alexander W H Speed; George A Moniz; Andreas Reichelt; Stephen Ho

doi:10.1021/ja900020a

An aldol-based synthesis of (+)-peloruside a, a potent microtubule stabilizing agent

J Am Chem Soc. 2009 Mar 25;131(11):3840-1. doi: 10.1021/ja900020a.

Authors

David A Evans¹, Dennie S Welch, Alexander W H Speed, George A Moniz, Andreas Reichelt, Stephen Ho

Affiliation

¹ Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA. evans@chemistry.harvard.edu

Abstract

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.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Alcohols
Aldehydes
Animals
Biological Products / chemical synthesis
Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
Lactones / chemical synthesis*
Porifera / chemistry
Stereoisomerism
Tubulin Modulators / chemical synthesis

Substances

Alcohols
Aldehydes
Biological Products
Bridged Bicyclo Compounds, Heterocyclic
Lactones
Tubulin Modulators
peloruside A

Abstract

Publication types

MeSH terms

Substances

Grants and funding