Total Synthesis of Halicylindramide A

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• 作者：Hyunju Seo ; Dongyeol Lim
• 刊名：Journal of Organic Chemistry
• 出版年：2009
• 出版时间：January 16, 2009
• 年：2009
• 卷：74
• 期：2
• 页码：906-909
• 全文大小：276K
• 年卷期：v.74,no.2(January 16, 2009)
• ISSN：1520-6904

文摘

A rapid and efficient Fmoc solid-phase synthesis of halicylindramide A is described. The strategy comprises resin attachment of the first amino acid via the side chain of aspartic acid, stepwise solid-phase synthesis of the linear peptide analog up to the cysteine residue, on-resin head-to-tail cyclization and linear peptide synthesis of the N-terminal region, and finally cysteine oxidation and formylation. The stereochemistry of the halicylindramide A was confirmed by comparison of NMR and RP-HPLC data with the natural molecule. A distinctive conformational change was observed from the CD spectra of the halicylindramide A in sodium dodecyl sulfate.