Efficient Synthesis of a Peculiar Vicinal Diamine Semiochemical from Streptomyces natalensis

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• 作者：Jesse B. Morin ; Jason K. Sello
• 刊名：Organic Letters
• 出版年：2010
• 出版时间：August 6, 2010
• 年：2010
• 卷：12
• 期：15
• 页码：3522-3524
• 全文大小：159K
• 年卷期：v.12,no.15(August 6, 2010)
• ISSN：1523-7052

文摘

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.