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Synthesis 2013; 45(20): 2888-2892
DOI: 10.1055/s-0033-1339658
DOI: 10.1055/s-0033-1339658
paper
Biology-Orientated Synthesis of Putrescine Bisamides Gigantamide A, Dasyclamide, and Cucullamide
Weitere Informationen
Publikationsverlauf
Received: 01. Mai 2013
Accepted after revision: 01. August 2013
Publikationsdatum:
15. August 2013 (online)
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 - synthesisSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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