Synthesis of amphidinolide E C10-C26 fragment

Org Lett. 2008 Nov 6;10(21):4843-6. doi: 10.1021/ol801923y. Epub 2008 Oct 7.

Abstract

The key C10-C26 fragment in a total synthesis of (-)-amphidinolide E has been prepared from an oxolane-containing C10-C17 segment (9, derived from L-glutamic acid) via a Julia-Kocienski reaction with aldehyde 3, followed by a Sharpless AD to obtain the desired diol. The C22-C26 fragment was installed by means of an efficient Suzuki-Molander coupling, with an organotrifluoroborate reagent (4, arising from a cross-metathesis reaction between a vinylboronate and 2-methyl-1,4-pentadiene).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkalies / chemistry
  • Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry
  • Carbon / chemistry*
  • Cross-Linking Reagents / chemistry
  • Hydrogen-Ion Concentration
  • Hydroxylation
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Structure

Substances

  • Alkalies
  • Bridged Bicyclo Compounds, Heterocyclic
  • Cross-Linking Reagents
  • amphidinolide E
  • Carbon