Formal synthesis of (±)-galanthamine and (±)-lycoramine using Rh(I)-catalyzed [(3 + 2) + 1] cycloaddition of 1-ene-vinylcyclopropane and CO

J Org Chem. 2015 Feb 6;80(3):1952-6. doi: 10.1021/jo502604p. Epub 2015 Jan 16.

Abstract

An efficient strategy using Rh(I)-catalyzed [(3 + 2) + 1] cycloaddition of 1-ene-vinylcyclopropane and CO as a key step to build the cis-hydrodibenzofuran skeleton has been developed and applied for the formal synthesis of (±)-galanthamine and (±)-lycoramine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amaryllidaceae Alkaloids / chemical synthesis*
  • Amaryllidaceae Alkaloids / chemistry*
  • Benzofurans / chemistry*
  • Catalysis
  • Cycloaddition Reaction
  • Galantamine / chemical synthesis*
  • Galantamine / chemistry*
  • Molecular Structure
  • Rhodium / chemistry*
  • Stereoisomerism
  • Vinyl Compounds / chemistry*

Substances

  • Amaryllidaceae Alkaloids
  • Benzofurans
  • Vinyl Compounds
  • Galantamine
  • Rhodium
  • lycoramine