Total synthesis of (-)-sessilifoliamide J

J Org Chem. 2013 Jan 4;78(1):35-41. doi: 10.1021/jo3014484. Epub 2012 Sep 14.

Abstract

An efficient synthesis of the Stemona alkaloid (-)-sessilifoliamide J (1) in 12 steps and 7.7% overall yield from the known building block 8 is presented. The synthesis features the Corey lactonization reaction and a highly diastereoselective α-methylation reaction to build the spiro-lactone moiety.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Lactones / chemical synthesis*
  • Lactones / chemistry
  • Molecular Structure
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry
  • Stemonaceae / chemistry
  • Stereoisomerism

Substances

  • Alkaloids
  • Lactones
  • Spiro Compounds
  • sessilifoliamide J