Biomimetic Total Synthesis of the Spiroindimicin Family of Natural Products

被引：8

作者：

Zheng, Xikang ^{[1
]}

Li, Yan ^{[1
]}

Guan, Mengtie ^{[1
]}

Wang, Lingyue ^{[1
]}

Wei, Shilong ^{[1
]}

Li, Yi-Cheng ^{[2
]}

Chang, Chin-Yuan ^{[2
]}

Xu, Zhengren ^{[1
]}

机构：

[1] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China

[2] Natl Yang Ming Chiao Tung Univ, Dept Biol Sci & Technol, Hsinchu 30010, Taiwan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2022年 / 61卷 / 38期

基金：

北京市自然科学基金; 中国国家自然科学基金;

关键词：

Bioinspired Synthesis; Chemo-Enzymatic Synthesis; Natural Products; Spirocyclization; Total Synthesis; LYCOGARUBIN C; GENE-CLUSTER; BIOSYNTHESIS; DERIVATIVES; TRYPTOPHAN; DISCOVERY; STAUROSPORINE; REBECCAMYCIN; STAP;

D O I：

10.1002/anie.202208802

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A unified strategy for the biomimetic total synthesis of the spiroindimicin family of natural products was reported. Key transformations include a one-pot two-enzyme-catalyzed oxidative dimerization of L-tryptophan/5-chloro-L-tryptophan to afford the bis-indole precursors chromopyrrolic acid/5 ',5 ''-dichloro-chromopyrrolic acid, and regioselective C3 '-C2 '' and C3 '-C4 '' bond formation converting a common bis-indole skeleton to two skeletally different natural products, including (+/-)-spiroindimicins D and G with a [5,5] spiro-ring skeleton, and (+/-)-spiroindimicins A and H with a [5,6] spiro-ring skeleton, respectively.

引用

页数：6

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