Synthesis of the C1'-C11' oxazole-containing side chain of leucascandrolide A. Application of a Sonogashira cross-coupling

J Org Chem. 2002 Sep 20;67(19):6812-5. doi: 10.1021/jo0204000.

Abstract

An efficient, convergent synthesis of the C1'-C11' side chain (3) of leucascandrolide A (1) has been achieved. The key bond connection is made through the use of a palladium(0)-catalyzed Sonogashira cross-coupling between trifloyl oxazole (4) and alkynylmetal species (5).

Publication types

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

MeSH terms

  • Alkynes / chemistry*
  • Animals
  • Catalysis
  • Cross-Linking Reagents / chemistry*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Organometallic Compounds / chemistry
  • Oxazoles / chemistry*
  • Palladium / chemistry*
  • Porifera / chemistry*
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / chemistry
  • Structure-Activity Relationship

Substances

  • Alkynes
  • Cross-Linking Reagents
  • Organometallic Compounds
  • Oxazoles
  • Sesquiterpenes
  • leucascandrolide A
  • Palladium