Asymmetric Total Synthesis and Stereochemical Revision of Gymnangiamide

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• 作者：Hitoshi Tone ; Marie Buchotte ; Cline Mordant ; Eric Guittet ; Tahar Ayad ; Virginie Ratovelomanana-Vidal
• 刊名：Organic Letters
• 出版年：2009
• 出版时间：May 7, 2009
• 年：2009
• 卷：11
• 期：9
• 页码：1995-1997
• 全文大小：136K
• 年卷期：v.11,no.9(May 7, 2009)
• ISSN：1523-7052

文摘

The asymmetric total synthesis of the originally proposed structure of gymnangiamide, a cytotoxic pentapeptide isolated from the marine hydroid Gymnangium regae Jaderholm, has been achieved. Key to the synthesis was the use of asymmetric hydrogenation of α-substituted β-ketoesters through dynamic kinetic resolution for the preparation of nonproteinogenic chiral amino acids. The disparity of the NMR spectra between the synthetic material containing the l-serine residue and the natural product required a revision of the proposed structure.