Formal syntheses of (+/-)-stemonamine and (+/-)-cephalotaxine

J Org Chem. 2009 Apr 17;74(8):3211-3. doi: 10.1021/jo900113s.

Abstract

A short and efficient approach to aza-quaternary pyrrolo[1,2-a]azepine 8 and aza-quaternary indolizine 23, as the crucial intermediates for syntheses of stemonamine (1a) and cephalotaxine (1b), has been developed on the basis of the key intramolecular Schmidt reaction of symmetric azido-diones 5 and 18, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemical synthesis
  • 4-Butyrolactone / chemistry
  • Azepines / chemical synthesis
  • Azepines / chemistry*
  • Azides / chemistry*
  • Catalysis
  • Harringtonines / chemical synthesis*
  • Harringtonines / chemistry
  • Homoharringtonine
  • Magnetic Resonance Spectroscopy
  • Molecular Structure

Substances

  • Azepines
  • Azides
  • Harringtonines
  • stemonamine
  • Homoharringtonine
  • 4-Butyrolactone