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  • Title: An aza-Wittig/pi-furan cyclization approach toward the homoerythrina alkaloid (+/-)-selaginoidine.
    Author: Cassidy MP, Ozdemir AD, Padwa A.
    Journal: Org Lett; 2005 Mar 31; 7(7):1339-42. PubMed ID: 15787501.
    Abstract:
    [reaction: see text] 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.
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