Total synthesis of (+)-peloruside A

Org Lett. 2005 Mar 31;7(7):1303-5. doi: 10.1021/ol050070g.

Abstract

[reaction: see text] A total synthesis of (+)-peloruside A has been successfully achieved. The strategy was highlighted by a late stage aldol coupling of two complex fragments followed by an intramolecular hemi-ketal cyclization, a MOM group participated epoxide ring fragmentation reaction, and a highly selective methylation. This convergent route allows access to rationally designed analogues.

Publication types

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

MeSH terms

  • Animals
  • Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
  • Cyclization
  • Lactones / chemical synthesis*
  • Molecular Structure
  • Porifera / chemistry
  • Stereoisomerism

Substances

  • Bridged Bicyclo Compounds, Heterocyclic
  • Lactones
  • peloruside A