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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"