Intramolecular cyclopropanation of glycals: studies toward the synthesis of canadensolide, sporothriolide, and xylobovide

Org Lett. 2001 Aug 9;3(16):2563-6. doi: 10.1021/ol016239h.

Abstract

[reaction: see text] The first examples of copper-catalyzed intramolecular cyclopropanations of glycal-derived diazoacetates are reported. The new cyclopropanes are converted into advanced intermediates for the synthesis of bislactone natural products. Synthetic highlights include the selective monodeprotection of a di-tert-butylsilylene ether and a zinc-mediated ring opening cascade reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Crystallography, X-Ray
  • Cyclization
  • Furans / chemical synthesis*
  • Indicators and Reagents
  • Lactones / chemical synthesis*
  • Molecular Conformation
  • Palladium
  • Propane / chemistry

Substances

  • Furans
  • Indicators and Reagents
  • Lactones
  • canadensolide
  • xylobovide
  • sporothriolide
  • Palladium
  • Propane