Catalytic enantioselective total synthesis of (-)-platyphyllide and its structural revision

J Org Chem. 2010 Jun 4;75(11):3871-4. doi: 10.1021/jo1003746.

Abstract

The catalytic asymmetric total synthesis of platyphyllide has been accomplished. A key highly substituted cyclohexene derivative has been obtained by the catalytic asymmetric Diels-Alder reaction of Danishefsky diene with an electron-deficient alkene. The Diels-Alder adduct was converted to a protected cyclohexane-1,3-dione in chiral form by catalytic Ito-Saegusa oxidation. Although the reported structure of platyphyllide was successfully synthesized, the optical rotation was opposite that of the natural compound. The absolute configuration of natural (-)-platyphyllide is revised to be a (6S,7S)-enantiomer.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry
  • Benzofurans
  • Catalysis
  • Cyclohexanes
  • Cyclohexenes / chemical synthesis*
  • Cyclohexenes / chemistry*
  • Ketones
  • Molecular Structure
  • Optical Rotation
  • Stereoisomerism

Substances

  • Alkenes
  • Benzofurans
  • Cyclohexanes
  • Cyclohexenes
  • Ketones
  • platyphyllide
  • cyclohexene
  • Cyclohexane