Catalytic enantioselective total synthesis of (+)-eucomic acid

被引：11
|
作者：
Estipona, Benzi I. [1 ]
Pritchett, Beau P. [1 ]
Craig, Robert A., II [1 ]
Stoltz, Brian M. [1 ]
机构：
[1] CALTECH, Warren & Katharine Schlinger Lab Chem & Chem Engn, 1200 E Calif Blvd,MC 101-20, Pasadena, CA 91125 USA
来源：
TETRAHEDRON | 2016年 / 72卷 / 26期
基金：
美国国家卫生研究院;
关键词：
Allylic alkylation; Enantioselective; Eucomic acid; Palladium; Total synthesis; HARRINGTONIA VAR DRUPACEA; (R)-EUCOMIC ACID; DERIVATIVES; (+)-DRAGMACIDIN-F; ALKYLATION; COMPLEXES; ALKALOIDS;
D O I：
10.1016/j.tet.2016.02.059
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A catalytic enantioselective synthesis of (+)-eucomic acid is reported. A palladium-catalyzed asymmetric allylic alkylation is employed to access the chiral tetrasubstituted alpha-hydroxyacid moiety found in the natural product. The protecting group strategy was investigated, and a protecting group manipulation was made without any appreciable deleterious effects in the allylic alkylation reaction. Non-natural (+)-eucomic acid is synthesized in a longest linear sequence of 13 steps. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3707 / 3712
页数：6
相关论文
共 50 条
  • [41] Atropisomeric lactam chemistry: catalytic enantioselective synthesis, application to asymmetric enolate chemistry and synthesis of key intermediates for NET inhibitors
    Takahashi, Masashi
    Tanabe, Hajime
    Nakamura, Tsuyoshi
    Kuribara, Daisuke
    Yamazaki, Toshiyuki
    Kitagawa, Osamu
    TETRAHEDRON, 2010, 66 (01) : 288 - 296
  • [42] A Concise Enantioselective Total Synthesis of (-)-Deoxoapodine
    Yoshida, Kei
    Okada, Kosuke
    Ueda, Hirofumi
    Tokuyama, Hidetoshi
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (51) : 23089 - 23093
  • [43] Enantioselective Total Synthesis of (+)-Nocardioazine B
    Shen, Xianfu
    Zhao, Jingfeng
    Xi, Yongkai
    Chen, Wen
    Zhou, Yongyun
    Yang, Xiaodong
    Zhang, Hongbin
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (23) : 14507 - 14517
  • [44] Enantioselective total synthesis of Wieland-Gumlich aldehyde and (-)-strychnine
    Solé, D
    Bonjoch, J
    García-Rubio, S
    Peidró, E
    Bosch, J
    CHEMISTRY-A EUROPEAN JOURNAL, 2000, 6 (04) : 655 - 665
  • [45] Catalytic Asymmetric Total Synthesis of (-)-Galanthamine and (-)-Lycoramine
    Li, Lei
    Yang, Qiao
    Wang, Yuan
    Jia, Yanxing
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (21) : 6255 - 6259
  • [46] An efficient homogeneous catalytic enantioselective synthesis of α-amino acid derivatives
    O'Donnell, MJ
    Delgado, F
    Hostettler, C
    Schwesinger, R
    TETRAHEDRON LETTERS, 1998, 39 (48) : 8775 - 8778
  • [47] A short enantioselective total synthesis of (R)- and (S)-pipecolic acid
    Chavan, Subhash P.
    Khairnar, Lalit B.
    Chavan, Prakash N.
    Kalbhor, Dinesh B.
    TETRAHEDRON-ASYMMETRY, 2014, 25 (16-17) : 1246 - 1251
  • [48] Catalytic enantioselective synthesis of axially chiral allenes
    Ogasawara, Masamichi
    TETRAHEDRON-ASYMMETRY, 2009, 20 (03) : 259 - 271
  • [49] Catalytic Enantioselective Desymmetrization of Meso Compounds in Total Synthesis of Natural Products: Towards an Economy of Chiral Reagents
    Merad, Jeremy
    Candy, Mathieu
    Pons, Jean-Marc
    Bressy, Cyril
    SYNTHESIS-STUTTGART, 2017, 49 (09): : 1938 - 1954
  • [50] Enantioselective Total Synthesis of (+)-Incargranine A Enabled by Bifunctional Iminophosphorane and Iridium Catalysis
    Miller, Anna A. M.
    Biallas, Phillip
    Shennan, Benjamin D. A.
    Dixon, Darren J.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (02)
12345