Enantioselective total synthesis of the lignan (+)-linoxepin

Chemistry. 2014 Dec 15;20(51):17119-24. doi: 10.1002/chem.201404679. Epub 2014 Oct 24.

Abstract

An enantioselective total synthesis of the natural (+)-linoxepin (1) was accomplished in eleven steps from bromovanin (24). Key steps are a domino carbopalladation/ Mizoroki-Heck reaction with the formation of a pentacyclic system, an asymmetric hydroboration as well as an oxidative lactonization.

Keywords: asymmetric hydroboration; carbopalladation; lignans; natural products; total synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzaldehydes / chemistry*
  • Lignans / chemical synthesis*
  • Lignans / chemistry*
  • Molecular Structure
  • Oxidation-Reduction
  • Polycyclic Compounds / chemical synthesis*
  • Polycyclic Compounds / chemistry*
  • Stereoisomerism

Substances

  • Benzaldehydes
  • Lignans
  • Polycyclic Compounds
  • bromovanin
  • linoxepin