Novel Skeleton Transformation Reaction of α-pyrone Derivatives to spirobicyclo[3.1.0]hexane Derivatives Using Dimethylsulfoxonium Methylide

Org Lett. 2012 Dec 7;14(23):6048-51. doi: 10.1021/ol302942m. Epub 2012 Nov 19.

Abstract

By applying a skeleton transformation reaction using dimethylsulfoxonium methylide, a novel reaction was identified by which 5,6,7,8-tetrahydrocoumarin with the electron-withdrawing group at C3 was led to the spirobicyclo[3.1.0]hexane-cyclohexane derivative. Moreover, by establishing the scope of this reaction, it was confirmed that it is possible to apply this reaction to not only ring-fused α-pyrone derivatives but also alkyl-chain-substituted α-pyrone derivatives in moderate to good yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bridged Bicyclo Compounds / chemical synthesis*
  • Bridged Bicyclo Compounds / chemistry
  • Hexanes / chemistry*
  • Molecular Structure
  • Pyrones / chemistry*
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry
  • Stereoisomerism
  • Sulfonium Compounds / chemistry*

Substances

  • Bridged Bicyclo Compounds
  • Hexanes
  • Pyrones
  • Spiro Compounds
  • Sulfonium Compounds
  • dimethylsulfoxonium methylide
  • n-hexane