Total synthesis of (+/-)-rhazinal using novel palladium-catalyzed cyclizations

J Org Chem. 2009 Feb 20;74(4):1581-6. doi: 10.1021/jo801791j.

Abstract

A concise synthesis of (+/-)-rhazinal that hinges on novel oxidative Heck cyclizations and palladium-catalyzed direct couplings is described. An X-ray structure of N-MOM-rhazinal, which provides insight into the conformation of the strained 9-membered lactam ring, is described.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemical synthesis*
  • Aldehydes / chemistry
  • Amides / chemistry
  • Catalysis
  • Cyclization
  • Indolizines / chemical synthesis*
  • Indolizines / chemistry
  • Oxidation-Reduction
  • Palladium / chemistry*
  • Pyrroles / chemistry
  • Stereoisomerism

Substances

  • Aldehydes
  • Amides
  • Indolizines
  • Pyrroles
  • rhazinal
  • indolizine
  • Palladium