Dragmacidin E synthesis studies. Preparation of a model cycloheptannelated indole fragment

Ken S. Feldman; Paiboon Ngernmeesri

doi:10.1021/ol0522081

Dragmacidin E synthesis studies. Preparation of a model cycloheptannelated indole fragment

Ken S. Feldman
, Paiboon Ngernmeesri

Chemistry

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

42 Scopus citations

Abstract

(Chemical Equation Presented) The conversion of N-2,2-dichloropropionyl indole methyl ester into a tetracyclic cycloheptannelated indole model compound for the synthesis of dragmacidin E was accomplished in 10 steps. Key reactions include a Witkop cyclization to fashion a C-C bond at C(4) of the indole nucleus and a subsequent Dieckmann cyclization to deliver the desired cycloheptanoid ring.

Original language	English (US)
Pages (from-to)	5449-5452
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	24
DOIs	https://doi.org/10.1021/ol0522081
State	Published - Nov 24 2005

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol0522081

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title = "Dragmacidin E synthesis studies. Preparation of a model cycloheptannelated indole fragment",

abstract = "(Chemical Equation Presented) The conversion of N-2,2-dichloropropionyl indole methyl ester into a tetracyclic cycloheptannelated indole model compound for the synthesis of dragmacidin E was accomplished in 10 steps. Key reactions include a Witkop cyclization to fashion a C-C bond at C(4) of the indole nucleus and a subsequent Dieckmann cyclization to deliver the desired cycloheptanoid ring.",

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year = "2005",

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journal = "Organic Letters",

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AU - Feldman, Ken S.

AU - Ngernmeesri, Paiboon

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N2 - (Chemical Equation Presented) The conversion of N-2,2-dichloropropionyl indole methyl ester into a tetracyclic cycloheptannelated indole model compound for the synthesis of dragmacidin E was accomplished in 10 steps. Key reactions include a Witkop cyclization to fashion a C-C bond at C(4) of the indole nucleus and a subsequent Dieckmann cyclization to deliver the desired cycloheptanoid ring.

AB - (Chemical Equation Presented) The conversion of N-2,2-dichloropropionyl indole methyl ester into a tetracyclic cycloheptannelated indole model compound for the synthesis of dragmacidin E was accomplished in 10 steps. Key reactions include a Witkop cyclization to fashion a C-C bond at C(4) of the indole nucleus and a subsequent Dieckmann cyclization to deliver the desired cycloheptanoid ring.

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U2 - 10.1021/ol0522081

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EP - 5452

JO - Organic Letters

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ER -

Dragmacidin E synthesis studies. Preparation of a model cycloheptannelated indole fragment

Abstract

All Science Journal Classification (ASJC) codes

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