Total synthesis of (-)-18-epi-peloruside A: an alkyne linchpin strategy

Org Lett. 2013 Oct 18;15(20):5274-7. doi: 10.1021/ol4024997. Epub 2013 Oct 4.

Abstract

A convergent synthetic route toward cytotoxic agent peloruside A that hinges on the use of an alkyne linchpin to assemble the natural product is described. Other highlights of this synthesis include an asymmetric desymmetrization reaction of a 1,3-diol, a one-pot conversion of a dibromoolefin to a stereodefined enone, and a diastereoselective aldol condensation. Misassignment of the absolute stereochemistry of the C18 stereocenter in our synthesis provided the natural product epimeric at the C18 ethyl stereocenter.

Publication types

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

MeSH terms

  • Biological Products / chemical synthesis
  • Biological Products / chemistry
  • Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry
  • Lactones / chemical synthesis*
  • Lactones / chemistry
  • Molecular Conformation
  • Stereoisomerism

Substances

  • Biological Products
  • Bridged Bicyclo Compounds, Heterocyclic
  • Lactones
  • peloruside A