Total Synthesis of Oxidized Welwitindolinones and (-)-N-Methylwelwitindolinone C Isonitrile

被引：153

作者：

Quasdorf, Kyle W. ^{[1
]}

Huters, Alexander D. ^{[1
]}

Lodewyk, Michael W. ^{[2
]}

Tantillo, Dean J. ^{[2
]}

Garg, Neil K. ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

[2] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 03期

基金：

美国国家科学基金会;

关键词：

MULTIPLE-DRUG RESISTANCE; ISOTHIOCYANATE; WELWISTATIN; CONSTRUCTION; CORE; FISCHERINDOLES; HAPALINDOLES; NOBILISITINE; CYCLIZATION; EFFICIENT;

D O I：

10.1021/ja210837b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report the total synthesis of (-)-N-methylwelwitindolinone C isonitrile, in addition to the total syntheses of the 3-hydroxylated welwitindolinones. Our routes to these elusive natural products feature the strategic use of a deuterium kinetic isotope effect to improve the efficiency of a late-stage nitrene insertion reaction. We also provide a computational prediction for the stereochemical configuration at C3 of the hydroxylated welwitindolinones, which was confirmed by experimental studies.

引用

页码：1396 / 1399

页数：4

共 58 条

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