Stereoselective synthesis of (-)-1-epi-ventiloquinone L and (+)-ventiloquinone L, the monomeric unit of cardinalin 3

Org Biomol Chem. 2012 Jun 14;10(22):4462-6. doi: 10.1039/c2ob25453k. Epub 2012 Apr 26.

Abstract

A stereoselective synthesis of (-)-1-epi-ventiloquinone L and (+)-ventiloquinone L, the monomeric unit of cardinalin 3 has been described. The synthesis is completed in 7 steps with 10.5% and 13% overall yields for (-)-1-epi-ventiloquinone L and (+)-ventiloquinone L respectively. The key steps involve Dötz benzannulation of carbene 5 with alkyne 6 to give a substituted naphthalene moiety and oxa-Pictet-Spengler reaction to install the 1,3-dimethylpyran moiety.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzoquinones / chemistry*
  • Molecular Structure
  • Naphthoquinones / chemical synthesis*
  • Pyrans / chemical synthesis*
  • Stereoisomerism

Substances

  • Benzoquinones
  • Naphthoquinones
  • Pyrans
  • cardinalin 3
  • ventiloquinone L