A synthesis of the carbon skeleton of maoecrystal V

Org Lett. 2009 Nov 5;11(21):4774-6. doi: 10.1021/ol901963v.

Abstract

An enantioselective synthesis of the maoecrystal V (1) carbon skeleton is described. The key transformations include arylation of a 1,3-dicarbonyl compound with a triarylbismuth(V) dichloride species, oxidative dearomatization of a phenol, and a subsequent intramolecular Diels-Alder reaction.

Publication types

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

MeSH terms

  • Catalysis
  • Crystallography, X-Ray
  • Cyclization
  • Diterpenes / chemical synthesis*
  • Diterpenes / chemistry
  • Diterpenes / pharmacology
  • Drugs, Chinese Herbal / chemical synthesis*
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / pharmacology
  • Isodon / chemistry
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Stereoisomerism

Substances

  • Diterpenes
  • Drugs, Chinese Herbal
  • maoecrystal A