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Org Lett


Title:Efficient synthesis of a peculiar vicinal diamine semiochemical from Streptomyces natalensis
Author(s):Morin JB; Sello JK;
Address:"Department of Chemistry, Brown University, 324 Brook Street, Providence, Rhode Island 02912, USA"
Journal Title:Org Lett
Year:2010
Volume:12
Issue:15
Page Number:3522 - 3524
DOI: 10.1021/ol1013763
ISSN/ISBN:1523-7052 (Electronic) 1523-7052 (Linking)
Abstract:"The pimaricin-inducing (PI) factor, produced by Streptomyces natalensis is a proposed pheromone with a peculiar vicinal diamine structure. The first synthesis of this molecule is reported. It features oxidative dimerization of an aci-nitro anion derived from tris(hydroxymethyl)nitromethane and disproportionation catalyst-facilitated hydrogenation of the resulting vicinal tertiary dinitro compound. As the synthesis requires only four steps with no chromatographic separations, it provides a convenient route to prepare PI factor for biological studies and industrial applications"
Keywords:Catalysis Diamines/*chemical synthesis/chemistry Molecular Structure Natamycin/*isolation & purification/metabolism Streptomyces/*chemistry;
Notes:"MedlineMorin, Jesse B Sello, Jason K eng Research Support, Non-U.S. Gov't 2010/07/31 Org Lett. 2010 Aug 6; 12(15):3522-4. doi: 10.1021/ol1013763"

 
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