Parallel kinetic resolution approach to the cyathane and cyanthiwigin diterpenes using a cyclopropanation/Cope rearrangement

Angew Chem Int Ed Engl. 2009;48(13):2398-402. doi: 10.1002/anie.200806154.

Abstract

Parallel effort: Stereodivergent parallel kinetic resolution of a racemic mixture of dienes using Davies' [Rh(2){(S)-dosp}(4)] or [Rh(2){(R)-dosp}(4)] catalysts promotes a tandem vinyl diazoacetate cyclopropanation/Cope rearrangement sequence to afford two diastereomeric, enantioenriched cycloheptadienes, which correspond to the natural antipodes of the title diterpenoids (see scheme).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclization
  • Diterpenes / chemical synthesis
  • Diterpenes / chemistry*
  • Kinetics
  • Rhodium / chemistry
  • Stereoisomerism

Substances

  • Diterpenes
  • cyanthiwigin F
  • cyanthiwigin U
  • cyathane
  • Rhodium