Enantioselective synthesis of the ester side chain of homoharringtonine

被引：27
|
作者：
Keller, L [1 ]
Dumas, F [1 ]
d'Angelo, J [1 ]
机构：
[1] Univ Paris Sud, Ctr Etud Pharmaceut, CNRS, Unite Associee, F-92296 Chatenay Malabry, France
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 2003卷 / 13期
关键词：
asymmetric synthesis; Michael additions; ozonolysis; protecting groups; total synthesis;
D O I：
10.1002/ejoc.200300111
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Details of the synthesis of the methyl ester of the side chain of homoharringtonine, a natural product with antileukemic properties, are reported below. The key tactical element involved a Michael addition between the known chiral imine 4 and 2-acetoxyacrylonitrile (5), furnishing the adduct (2R,1'R)-6 with a high degree of regio- and stereoselectivity. This adduct was then converted into the target compound (R)-2 by a linear sequence of ten chemical operations, in 6.0% overall yield. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).
引用
收藏
页码：2488 / 2497
页数：10
相关论文
共 50 条
  • [31] A concise and enantioselective synthesis of a C-6O-acyl side chain equivalent of zaragozic acid A
    Nakamura, S
    Inagaki, J
    Kitaguchi, J
    Tatani, K
    Hashimoto, S
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1999, 47 (09) : 1330 - 1333
  • [32] Synthesis of Homoharringtonine and Harringtonine
    Dong, Yu
    Li, Haibo
    Li, Jin
    Feng, Lei
    Zhang, Zhiwei
    PROGRESS IN CHEMISTRY, 2018, 30 (12) : 1827 - 1835
  • [33] SYNTHESIS OF CLAVULONE DERIVATIVES - SELECTIVE CLEAVAGE OF ESTER BONDS AND ELONGATION OF ALPHA-SIDE CHAIN IN CLAVULONE
    IGUCHI, K
    KANETA, S
    NAGAOKA, H
    YAMADA, Y
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (01) : 65 - 68
  • [34] Synthesis and characterization of chiral side-chain liquid-crystalline polymer containing menthol ester
    Jiang, TY
    Zhang, BY
    Tian, M
    Wang, Y
    JOURNAL OF APPLIED POLYMER SCIENCE, 2003, 89 (10) : 2845 - 2851
  • [35] Synthesis and characterization of chiral side-chain liquid-crystalline polymer containing menthol ester
    Zhang, B.-Y. (baoyanzhang@hotmail.com), 1600, John Wiley and Sons Inc. (89):
  • [36] Synthetic studies of the HIV-1 protease inhibitive didemnaketals: stereocontrolled synthesis of an ester side chain
    Zhao, XZ
    Tu, YQ
    Peng, L
    Li, XQ
    Jia, YX
    TETRAHEDRON LETTERS, 2004, 45 (19) : 3713 - 3716
  • [37] Synthesis of ester side chain functionalized all-conjugated diblock copolythiophenes via the Rieke method
    Kudret, Suleyman
    Van den Brande, Niko
    Defour, Maxime
    Van Mele, Bruno
    Lutsen, Laurence
    Vanderzande, Dirk
    Maes, Wouter
    POLYMER CHEMISTRY, 2014, 5 (06) : 1832 - 1837
  • [38] Cinnamate ester containing liquid crystalline side chain polymers
    Whitcombe, M.J., 1600, (29):
  • [39] Synthesis of D-glucose-based azacrown ethers with phosphonoalkyl side chain and their application to enantioselective reaction.
    Novák, T
    Bakó, P
    Pete, B
    Keglevich, G
    Ludányi, K
    Töke, L
    MAGYAR KEMIAI FOLYOIRAT, 2000, 106 (04): : 171 - 176
  • [40] Asymmetric epoxidation of cis-alkenes with arabinose-derived ketones:: enantioselective synthesis of the side chain of Taxol®
    Shing, Tony K. M.
    Luk, To
    Lee, Chi M.
    TETRAHEDRON, 2006, 62 (28) : 6621 - 6629
12345