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Synthesis 2013; 45(20): 2888-2892
DOI: 10.1055/s-0033-1339658
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© Georg Thieme Verlag Stuttgart · New York

Biology-Orientated Synthesis of Putrescine Bisamides Gigantamide A, Dasyclamide, and Cucullamide

Ramesh U. Batwal
Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune 411 008, India   Fax: +91(20)25902629   Email: np.argade@ncl.res.in
,
Narshinha P. Argade*
Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune 411 008, India   Fax: +91(20)25902629   Email: np.argade@ncl.res.in
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Publication History

Received: 01 May 2013

Accepted after revision: 01 August 2013

Publication Date:
15 August 2013 (online)

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Abstract

Starting from putrescine and the requisite carboxylic acids­, first syntheses of bioactive natural products gigantamide A, dasyclamide, and cucullamide were accomplished in very good overall yields using an appropriate sequence of dehydrative coupling reactions. The syntheses of the corresponding dehomo analogues of these natural products are also described. Regioselective diisobutylaluminum hydride reduction of an unhindered carbonyl group in citraconimide is the key step.

Key words

diamines - dehydrative coupling reactions - regioselective reduction - natural and unnatural bisamides - synthesis

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