Total Synthesis of the Marine Natural Product Solomonamide B Necessitates Stereochemical Revision

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• 作者：K. Kashinath ; Gorakhnath R. Jachak ; Paresh R. Athawale ; Udaya Kiran Marelli ; Rajesh G. Gonnade ; D. Srinivasa Reddy
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：July 1, 2016
• 年：2016
• 卷：18
• 期：13
• 页码：3178-3181
• 全文大小：379K
• 年卷期：0
• ISSN：1523-7052

文摘

The first total synthesis of the proposed structure of solomonamide B has been achieved. However, the ¹H and ¹³C NMR spectral data of the synthesized compound was not exactly matching with that of the natural solomonamide B. This prompted us to revise the originally proposed structure, in particular, the stereochemistry of the nonpeptide part, which was confirmed by its total synthesis. During the course of the synthesis, we have developed an interesting hydroxy group directed Wacker oxidation of internal olefins in a macrocyclic setting.