Construction of the benzylic quaternary carbon center of zoanthenol by intramolecular Mizoroki-Heck reaction of enone

Org Lett. 2002 May 2;4(9):1627-30. doi: 10.1021/ol025852d.

Abstract

[reaction: see text]. Stereocontrolled synthesis of the ABC ring framework of zoanthenol has been achieved. Our studies show that a beta,beta-disubstituted enone can act as a good acceptor of arylpalladium intermediates in the formation of a congested benzylic quaternary carbon center through an intramoleculer Mizoroki-Heck reaction. The cis B/C ring system was stereoselectively converted to the trans-fused framework through a SmI2-promoted deoxygenation of the alpha-hydroxy ketone.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Bridged-Ring Compounds / chemistry*
  • Catalysis
  • Cyclization
  • Heterocyclic Compounds, Bridged-Ring / chemistry*
  • Indicators and Reagents
  • Molecular Conformation
  • Palladium / chemistry

Substances

  • Alkaloids
  • Bridged-Ring Compounds
  • Heterocyclic Compounds, Bridged-Ring
  • Indicators and Reagents
  • zoanthenol
  • Palladium