Total synthesis of (-)-stemospironine

Org Lett. 2001 Aug 23;3(17):2721-4. doi: 10.1021/ol016336a.

Abstract

[structure: see text]. A stereocontrolled total synthesis of the polycyclic Stemona alkaloid, (-)-stemospironine (1) has been achieved. Key transformations include the use of a Staudinger reaction leading to the aza-Wittig ring closure of the perhydroazepine system. Formation of the vicinal pyrrolidine butyrolactone is described via the stereoselective intramolecular capture of an intermediate aziridinium salt.

Publication types

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

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Magnetic Resonance Spectroscopy
  • Magnoliopsida / chemistry
  • Polycyclic Compounds / chemical synthesis*
  • Polycyclic Compounds / chemistry
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry

Substances

  • Alkaloids
  • Polycyclic Compounds
  • Spiro Compounds
  • stemospironine