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 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 7 Issue: 7
  • Publication Date: 2005
  • Doi Number: 10.1021/ol0501323
  • Journal Name: ORGANIC LETTERS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1339-1342
  • Istanbul Technical University Affiliated: No


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.