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

Cassidy M., Ozdemir A., PADWA A.

ORGANIC LETTERS, cilt.7, sa.7, ss.1339-1342, 2005 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 7 Sayı: 7
  • Basım Tarihi: 2005
  • Doi Numarası: 10.1021/ol0501323
  • Dergi Adı: ORGANIC LETTERS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1339-1342
  • İstanbul Teknik Üniversitesi Adresli: Hayır

Özet

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.