Application of a Palladium-Catalyzed C-H Functionalization/Indolization Method to Syntheses of cis-Trikentrin A and Herbindole B

被引：33
|
作者：
Leal, Raul A. [1 ]
Bischof, Caroline [1 ]
Lee, Youjin V. [1 ]
Sawano, Shota [1 ]
McAtee, Christopher C. [1 ]
Latimer, Luke N. [2 ]
Russ, Zachary N. [2 ]
Dueber, John E. [2 ]
Yu, Jin-Quan [3 ]
Sarpong, Richmond [1 ]
机构：
[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
[2] Univ Calif Berkeley, Dept Bioengn, Berkeley, CA 94720 USA
[3] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 39期
基金：
美国国家科学基金会;
关键词：
C-H activation; desymmetrization; indole alkaloids; indolization; natural products; C(SP(3))-H BONDS; NATURAL HERBINDOLES; ABSOLUTE STRUCTURES; ARYL CHLORIDES; (+/-)-CIS-TRIKENTRIN-A; DESYMMETRIZATION; AMINATION; (+/-)-TRANS-TRIKENTRIN-A; (+/-)-HERBINDOLE; AMIDATION;
D O I：
10.1002/anie.201605475
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We describe herein formal syntheses of the indole alkaloids cis-trikentrin A and herbindole B from a common meso-hydroquinone intermediate prepared by a ruthenium-catalyzed [2+2+1+1] cycloaddition that has not been used previously in natural product synthesis. Key steps include a sterically demanding Buchwald-Hartwig amination as well as a unique C(sp(3))-H amination/indole formation. Studies toward a selective desymmetrization of the meso-hydroquinone are also reported.
引用
收藏
页码：11824 / 11828
页数：5
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