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

Cassidy, MP; Ozdemir, Ayşe; PADWA, A

doi:10.1021/ol0501323

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

Atıf İçin Kopyala

Cassidy M., Ozdemir A. , PADWA A.

ORGANIC LETTERS, cilt.7, ss.1339-1342, 2005 (SCI İndekslerine Giren Dergi)

Cilt numarası: 7 Konu: 7
Basım Tarihi: 2005
Doi Numarası: 10.1021/ol0501323
Dergi Adı: ORGANIC LETTERS
Sayfa Sayıları: ss.1339-1342

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.