An Aza-Wittig/pi-Furan cyclization approach toward the homoerythrina alkaloid (+/-)-selaginoidine

Cassidy M., Ozdemir A. , PADWA A.

ORGANIC LETTERS, vol.7, no.7, pp.1339-1342, 2005 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 7 Issue: 7
  • Publication Date: 2005
  • Doi Number: 10.1021/ol0501323
  • Title of Journal : ORGANIC LETTERS
  • Page Numbers: pp.1339-1342

Abstract

A one-pot procedure was developed to efficiently prepare hexahydroindolinones containing a tethered furan ring. Reaction of a furanyl azide with Bu3P delivered the iminophosphorane, which was allowed to react with 1-methyl-(2-oxocyclohexyl)acetic acid to give the desired hexahydroindolinone ring system. Further treatment with trifluoroacetic acid afforded the tetracyclic lactam skeleton found in the alkaloid (+/-)-selaginoidine.