An aza-Wittig/pi-furan cyclization approach toward the homoerythrina alkaloid (+/-)-selaginoidine |
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Authors: | Cassidy Michael P Ozdemir Ayse Daut Padwa Albert |
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Institution: | Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA. |
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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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