Asymmetric synthesis of the chlorocyclopropane-containing callipeltoside A side chain

Org Lett. 2001 Feb 22;3(4):503-5. doi: 10.1021/ol0155182.

Abstract

[reaction: see text] The callipeltoside A chlorocyclopropyl-containing dienyne side chain has been synthesized in nine steps and 33% overall yield from commercially available 1,2,5,6-O-dicyclohexylidene-D-mannitol. The key steps in the synthesis are a highly diastereoselective cyclopropanation of a vinyl chloride allylic ether and a Suzuki cross-coupling to complete the carbon framework.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Cyclopropanes / chemical synthesis*
  • Macrolides*
  • Mannitol / analogs & derivatives
  • Mannitol / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • 1,2,5,6-O-dicyclohexylidenemannitol
  • Anti-Bacterial Agents
  • Cyclopropanes
  • Macrolides
  • callipeltoside A
  • Mannitol