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
相关论文
共 50 条
  • [21] Palladium-catalyzed arene C-H activation/ketone C-H functionalization reaction: route to spirodihydroindenones
    Zhang, Bo-Sheng
    Hua, Hui-Liang
    Gao, Lu-Yao
    Liu, Ce
    Qiu, Yi-Feng
    Zhou, Ping-Xin
    Zhou, Zhao-Zhao
    Zhao, Jia-Hui
    Liang, Yong-Min
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (07): : 1376 - 1379
  • [22] Insights into directing group ability in palladium-catalyzed C-H bond functionalization
    Desai, Lopa V.
    Stowers, Kara J.
    Sanford, Melanie S.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (40) : 13285 - 13293
  • [23] Palladium-Catalyzed C-H Functionalization ol Heteroarenes with Aryl Bromides and Chlorides
    Tamba, Shunsuke
    Okubo, Youhei
    Tanaka, Shota
    Monguchi, Daiki
    Mori, Atsunoii
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (20): : 6998 - 7001
  • [24] Insights into directing group ability in palladium-catalyzed C-H bond functionalization
    Desai, Lopa V.
    Stowers, Kara J.
    Sanford, Melanie S.
    Journal of the American Chemical Society, 2008, 130 (40): : 13285 - 13293
  • [25] Novel C-H functionalization of arenes: palladium-catalyzed synthesis of diaryl sulfides
    Anbarasan, Pazhamalai
    Neumann, Helfried
    Beller, Matthias
    CHEMICAL COMMUNICATIONS, 2011, 47 (11) : 3233 - 3235
  • [26] Model Complexes for the Palladium-Catalyzed Transannular C-H Functionalization of Alicyclic Amines
    Aguilera, Ellen Y.
    Sanford, Melanie S.
    ORGANOMETALLICS, 2019, 38 (01) : 138 - 142
  • [27] Synthesis of Imides by Palladium-Catalyzed C-H Functionalization of Aldehydes with Secondary Amides
    Bian, Yong-Jun
    Chen, Chao-Yue
    Huang, Zhi-Zhen
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (03) : 1129 - 1133
  • [28] Palladium-catalyzed alkenation of thiophenes and furans by regioselective C-H bond functionalization
    Zhao, Jinlong
    Huang, Lehao
    Cheng, Kai
    Zhang, Yuhong
    TETRAHEDRON LETTERS, 2009, 50 (23) : 2758 - 2761
  • [29] Synthesis of Polynuclear Aromatic Hydrocarbons by Palladium-catalyzed C-H Bond Functionalization
    Dewan, Mitali
    Bera, Sachinath
    Samanta, Shubhankar
    Kundu, Debasish
    Jana, Rathin
    CURRENT ORGANIC CHEMISTRY, 2024, 28 (18) : 1387 - 1403
  • [30] Platinum model studies for palladium-catalyzed oxidative functionalization of C-H bonds
    Dick, AR
    Kampf, JW
    Sanford, MS
    ORGANOMETALLICS, 2005, 24 (04) : 482 - 485
12345