Stereoselection in the prins-pinacol synthesis of 2,2-disubstituted 4-acyltetrahydrofurans. Enantioselective synthesis of (-)-citreoviral

Org Lett. 2000 Jan 27;2(2):223-6. doi: 10.1021/ol991315q.

Abstract

[reaction: see text] The condensation of allylic diols with unsymmetrical ketones proceeds with high stereoselection to form 2,2-disubstituted 4-acyltetrahydrofurans when the alpha-substituents of the ketone differ substantially in size. A Prins-pinacol condensation of this type is the central strategic step in an enantioselective synthesis of (-)-citreoviral.

Publication types

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

MeSH terms

  • Aurovertins / chemical synthesis*
  • Furans / chemical synthesis*
  • Mycotoxins / chemical synthesis
  • Neurotoxins / chemical synthesis
  • Stereoisomerism

Substances

  • Aurovertins
  • Furans
  • Mycotoxins
  • Neurotoxins
  • citreoviridin