Total Synthesis of trans,trans-Sanguinamide B and Conformational Isomers

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• 作者：Erinprit K. Singh ; Deborah M. Ramsey ; Shelli R. McAlpine
• 刊名：Organic Letters
• 出版年：2012
• 出版时间：March 2, 2012
• 年：2012
• 卷：14
• 期：5
• 页码：1198-1201
• 全文大小：331K
• 年卷期：v.14,no.5(March 2, 2012)
• ISSN：1523-7052

文摘

The first total synthesis of Sanguinamide B is reported, prepared via an efficient synthetic strategy. The natural product, trans,trans-Sanguinamide B (1), was generated in a thermodynamic ratio with trans,cis-Sanguinamide B (2) and cis,cis-Sanguinamide B (3). Complete conversion of the cis,cis-Sanguinamide B conformer (3) to the natural product (1) and the trans,cis- conformer (2) was achieved by heating to 170 掳C. Biological evaluation indicated that the Sanguinamide B conformers disrupted the activity of a virulence determinant in P. aeruginosa.