Total synthesis of (±)-maistemonine and (±)-stemonamide

Chem Commun (Camb). 2011 Feb 14;47(6):1836-8. doi: 10.1039/c0cc02612c. Epub 2010 Dec 1.

Abstract

The first total synthesis of polycyclic Stemona alkaloid maistemonine has been achieved. The efficient approach features a stereoselective intramolecular Schmidt reaction, a ketone-ester condensation, and a Reformatsky reaction. Additionally, another Stemona alkaloid stemonamide was divergently synthesized from a common intermediate.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Esters / chemistry
  • Ketones / chemistry
  • Models, Chemical
  • Polycyclic Compounds / chemical synthesis*
  • Polycyclic Compounds / chemistry
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry
  • Stemonaceae / metabolism*
  • Stereoisomerism

Substances

  • Alkaloids
  • Esters
  • Ketones
  • Polycyclic Compounds
  • Spiro Compounds
  • stemonamide