Total Synthesis of Anti-HIV Agent Chloropeptin I

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• 作者：Hongbo Deng ; Jae-Kyung Jung ; Tao Liu ; Kevin W. Kuntz ; Marc L. Snapper ; and Amir H. Hoveyda
• 刊名：Journal of the American Chemical Society
• 出版年：2003
• 出版时间：July 30, 2003
• 年：2003
• 卷：125
• 期：30
• 页码：9032 - 9034
• 全文大小：115K
• 年卷期：v.125,no.30(July 30, 2003)
• ISSN：1520-5126

文摘

A convergent diastereo- and enantioselective total synthesis of anti-HIV agent chloropeptin I is reported. Important features of the total synthesis include: (1) the use of Ti-catalyzed cyanide addition to imines to prepare a requisite amino acid moiety, (2) the discovery of the positive effect of MeOH in the Cu-mediated biaryl ether formation to afford one of the two macrocyclic peptide moieties, and (3) the discovery of the positive influence of collidine in the diastereoselective Pd-mediated cross-coupling to result in efficient formation of another macrocycle within this medicinally important molecule. This key step is performed in the presence of four unprotected phenols, two of which reside on dichlorophenylglycines.