A flexible synthesis of novel homoharringtonine ester chain

被引:2
|
作者
Thi Hong Nhung Nguyen [1 ]
Thai Thanh Thu Bui [1 ]
Phong Van Pham [2 ]
Dinh Hung Mac [1 ]
机构
[1] VNU Univ Sci, Med Chem Lab, Fac Chem, 19 Le Thanh Tong, Hanoi, Vietnam
[2] VNU Univ Sci, Catalysis Lab, Fac Chem, 19 Le Thanh Tong, Hanoi, Vietnam
关键词
Mizoroki-Heck reaction; Boronic acids; Homoharringtonine; D-Malic acid; HECK TYPE REACTION; ALKALOIDS; BOND;
D O I
10.1016/j.tetlet.2015.12.012
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New homoharringtonine ester chains bearing aryl substituents were obtained using a flexible synthesis. D-Malic acid was utilized to achieve the diastereoselective allylation at the C2' center. A key oxidative Mizoroki-Heck reaction allowed the coupling of various phenyl boronic acids with the allyl intermediate to provide arylated products in excellent yields. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:216 / 218
页数:3
相关论文
共 50 条
  • [1] Enantioselective synthesis of the ester side chain of homoharringtonine
    Keller, L
    Dumas, F
    d'Angelo, J
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (13) : 2488 - 2497
  • [2] Enantioselective synthesis of the ester side chain of homoharringtonine
    Keller, L
    Dumas, F
    d'Angelo, J
    TETRAHEDRON LETTERS, 2001, 42 (10) : 1911 - 1913
  • [3] Enantioselective synthesis of the ester side chain of homoharringtonine
    Hue, Vu T.
    Nhung, Nguyen T. H.
    Hung, Mac D.
    ARKIVOC, 2014, : 206 - 212
  • [4] Synthesis of the ester side chains of homoharringtonine and harringtonine using lactones as building blocks
    Dang, Fang-Fang
    Wang, Cui-Cui
    Han, Feng
    Zhang, Zhi-Wei
    SYNTHETIC COMMUNICATIONS, 2021, 51 (02) : 317 - 323
  • [6] Novel Polyaspartic Ester Polyureas Based on Flexible Polyaspartic Ester
    Lu, Ping
    Huang, Wei-bo
    Ma, Xue-qiang
    Liu, Xu-dong
    NEW AND ADVANCED MATERIALS, PTS 1 AND 2, 2011, 197-198 : 1294 - 1298
  • [7] TOTAL SYNTHESIS OF HOMOHARRINGTONINE
    HUDLICKY, T
    HIRANUMA, S
    SHIBATA, M
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1983, 185 (MAR): : 8 - ORGN
  • [8] Synthesis of novel organocobalt polymers with flexible aliphatic spacers in the main chain
    Rozhanskii, IL
    Tomita, I
    Endo, T
    MACROMOLECULES, 1996, 29 (06) : 1934 - 1938
  • [9] Synthesis of Homoharringtonine and Harringtonine
    Dong, Yu
    Li, Haibo
    Li, Jin
    Feng, Lei
    Zhang, Zhiwei
    PROGRESS IN CHEMISTRY, 2018, 30 (12) : 1827 - 1835
  • [10] A concise and scalable formal synthesis of the enantiopure side-chain diester of homoharringtonine
    Sun, Moran
    Jia, Xin
    Lai, Yaowen
    Yang, Hua
    JOURNAL OF CHEMICAL RESEARCH, 2015, (01) : 26 - 29