Enantioselective synthesis of (+)- and (-)-dihydroepiepoformin and (+)-epiepoformin

Org Lett. 2005 Mar 31;7(7):1419-22. doi: 10.1021/ol050287a.

Abstract

[reaction: see text] The enantioselective synthesis of both enantiomers of dihydroepiepoformin (1) and (+)-epiepoformin (2) was achieved from (p-tolylsulfinyl)methyl-p-quinols (SR)- or (SS)-3 and (4R,SR)-4, respectively. Key features include the stereocontrolled conjugate addition of AlMe3 to p-quinol 3 and retrocondensation to the ketone functionality, previous to oxidation of the beta-hydroxy sulfoxide moiety of advanced intermediates to the corresponding sulfone.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
  • Catalysis
  • Hydroquinones / chemistry*
  • Ketones / chemistry*
  • Molecular Structure
  • Oxidation-Reduction
  • Penicillium / chemistry
  • Stereoisomerism
  • Sulfoxides / chemistry*

Substances

  • Bridged Bicyclo Compounds, Heterocyclic
  • Hydroquinones
  • Ketones
  • Sulfoxides
  • dihydroepiepoformin
  • epiepoformin