Synthesis of (-)-pericosine B, the antipode of the cytotoxic marine natural product

Org Biomol Chem. 2009 Jan 21;7(2):315-8. doi: 10.1039/b813072h. Epub 2008 Nov 13.

Abstract

The stereoselective synthesis of (-)-pericosine B, which is the antipode of the cytotoxic metabolite of the fungus Periconia byssoides OUPS-N133 separated from the sea hare, was accomplished in 9 steps in 12% total yield from (-)-quinic acid, together with the synthesis of its epimer. Every crucial step of this total synthesis, including ring opening of a beta-epoxide and NaBH4 reduction of an unstable beta,gamma-unsaturated enone, proceeded with excellent stereoselectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Products / chemical synthesis
  • Biological Products / toxicity
  • Cell Line, Tumor
  • Humans
  • Shikimic Acid / analogs & derivatives*
  • Shikimic Acid / chemical synthesis
  • Shikimic Acid / toxicity
  • Stereoisomerism

Substances

  • Biological Products
  • pericosine B
  • Shikimic Acid