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Org Lett. 2005 Nov 24;7(24):5449-52.

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

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1
Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA. ksf@chem.psu.edu

Abstract

[reaction: see text] 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.

PMID:
16288528
DOI:
10.1021/ol0522081
[Indexed for MEDLINE]
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