Total synthesis of dendrobate alkaloid (+)-241D, isosolenopsin and isosolenopsin A: application of a gold-catalyzed cyclization

Org Biomol Chem. 2012 Aug 7;10(29):5541-6. doi: 10.1039/c2ob25685a. Epub 2012 Jun 18.

Abstract

A new approach to total syntheses of piperidine alkaloids (+)-241D, isosolenopsin and isosolenopsin A has been developed from D-alanine. The key step to access the chiral pyridinone intermediate was achieved via a gold mediated cyclization. Finally, various reduction conditions afforded the natural products in few steps and good overall yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alanine / chemistry
  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Catalysis
  • Cyclization
  • Gold / chemistry*
  • Piperidines / chemical synthesis*
  • Piperidines / chemistry
  • Pyridones / chemistry
  • Stereoisomerism

Substances

  • 241D dendrobate alkaloid
  • Alkaloids
  • Piperidines
  • Pyridones
  • Solenopsin A
  • Gold
  • Alanine