An aza-wittig/π-furan cyclization approach toward the homoerythrina alkaloid (±)-selaginoidine

Michael P. Cassidy; Ayse Daut Özdemir; Albert Padwa

doi:10.1021/ol0501323

An aza-wittig/π-furan cyclization approach toward the homoerythrina alkaloid (±)-selaginoidine

Michael P. Cassidy, Ayse Daut Özdemir, Albert Padwa^*

^*Corresponding author for this work

Emory University

Research output: Contribution to journal › Article › peer-review

34 Citations (Scopus)

Abstract

(Chemical Equation Presented) 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.

Original language	English
Pages (from-to)	1339-1342
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	7
DOIs	https://doi.org/10.1021/ol0501323
Publication status	Published - 31 Mar 2005
Externally published	Yes

Funding

Funders	Funder number
National Institute of General Medical Sciences	R01GM059384

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10.1021/ol0501323

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title = "An aza-wittig/π-furan cyclization approach toward the homoerythrina alkaloid (±)-selaginoidine",

abstract = "(Chemical Equation Presented) 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.",

author = "Cassidy, {Michael P.} and {\"O}zdemir, {Ayse Daut} and Albert Padwa",

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AU - Özdemir, Ayse Daut

AU - Padwa, Albert

PY - 2005/3/31

Y1 - 2005/3/31

N2 - (Chemical Equation Presented) 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.

AB - (Chemical Equation Presented) 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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An aza-wittig/π-furan cyclization approach toward the homoerythrina alkaloid (±)-selaginoidine

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