Stereocontrolled and Efficient Total Synthesis of (−)-Stephanotic Acid Methyl Ester and (−)-Celogentin C

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• 作者：Weimin Hu ; Fengying Zhang ; Zhengren Xu ; Qiang Liu ; Yuxin Cui ; Yanxing Jia
• 刊名：Organic Letters
• 出版年：2010
• 出版时间：March 5, 2010
• 年：2010
• 卷：12
• 期：5
• 页码：956-959
• 全文大小：244K
• 年卷期：v.12,no.5(March 5, 2010)
• ISSN：1523-7052

文摘

A highly stereocontrolled and efficient total synthesis of (−)-stephanotic acid methyl ester and (−)-celogentin C was accomplished in longest linear 14 steps (4.6% overall yield) and in 20 steps (1.6% overall yield) from l-tryptophan, respectively. Highlights of the synthesis include a tandem asymmetric Michael addition/bromination/azidation strategy for a ready access to the leucine-tryptophan moiety (Leu-Trp linkage) and an oxidative coupling reaction to form the indole-imidazole linkage.