Total synthesis of jimenezin via an intramolecular allylboration

Org Lett. 2006 Aug 17;8(17):3829-31. doi: 10.1021/ol0614471.

Abstract

[structure: see text] An efficient total synthesis of the annonaceous acetogenin jimenezin was achieved. The key steps used were a highly stereoselective intramolecular allylboration to establish the tetrahydropyran ring and an intramolecular Williamson reaction to close the tetrahydrofuran ring.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetogenins
  • Fatty Alcohols / chemistry
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Lactones / chemistry
  • Molecular Structure
  • Plants, Medicinal / chemistry
  • Pyrans / chemical synthesis*
  • Pyrans / chemistry
  • Rollinia / chemistry
  • Stereoisomerism

Substances

  • Acetogenins
  • Fatty Alcohols
  • Furans
  • Lactones
  • Pyrans
  • jimenezin