Lipase-catalyzed transesterification of methyl 2-substituted 3-hydroxy-4-pentenoates and its synthetic application to the taxol side chain

被引：14
|
作者：
Mandai, T [1 ]
Oshitari, T [1 ]
Susowake, M [1 ]
机构：
[1] Kurashiki Univ Sci & Arts, Dept Chem & Biosci, Kurashiki, Okayama 7128505, Japan
来源：
SYNLETT | 2002年 / 10期
关键词：
syn and anti-methyl 2-substituted 3-hydroxy-4-pentenoates; lipase-catalyzed kinetic resolution; 1,2-amino alcohols; the taxol side chain;
D O I：
10.1055/s-2002-34247
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Syn-and anti-methyl 2-substituted 3-hydroxy-4-pentenoates were efficiently resolved in lipase-catalyzed transesterification. This protocol was successfully applied to the synthesis of the taxol side chain.
引用
收藏
页码：1665 / 1668
页数：4
相关论文
共 50 条
  • [1] Lipase catalyzed transesterification of 2-substituted 3-hydroxy esters
    Kaga, H
    Hirosawa, K
    Takahashi, T
    Goto, K
    CHIRALITY, 1998, 10 (07) : 693 - 698
  • [2] Lipase-catalyzed transesterification as a practical route to homochiral syn-1,2-diols.: The synthesis of the taxol side chain
    Lee, D
    Kim, MJ
    TETRAHEDRON LETTERS, 1998, 39 (15) : 2163 - 2166
  • [3] LIPASE-CATALYZED RESOLUTION OF 2-SUBSTITUTED 3-CYCLOPENTEN-1-OL DERIVATIVES
    SAKAI, T
    IIDA, Y
    KIKUYAMA, S
    TSUBOI, S
    UTAKA, M
    CHEMISTRY LETTERS, 1991, (09) : 1651 - 1652
  • [4] Lipase-catalyzed enantioselective transesterification of 3-hydroxy-3-(2-thienyl) propanenitrile in liquid carbon dioxide
    Zhang, Jiaxin
    Li, Yazhuo
    Qian, Wenwei
    Zhang, Liu
    Li, Fengxi
    Chen, Peng
    Wang, Lei
    GREEN CHEMISTRY LETTERS AND REVIEWS, 2018, 11 (03) : 224 - 229
  • [5] Asymmetric synthesis of 2-substituted chroman-4-ones using lipase-catalyzed kinetic resolutions
    Kawasaki, M
    Kakuda, H
    Goto, M
    Kawabata, S
    Kometani, T
    TETRAHEDRON-ASYMMETRY, 2003, 14 (11) : 1529 - 1534
  • [6] LIPASE-CATALYZED KINETIC RESOLUTION OF METHYL 4-HYDROXY-5-TETRADECYNOATE AND ITS APPLICATION TO A FACILE SYNTHESIS OF JAPANESE-BEETLE PHEROMONE
    FUKUSAKI, E
    SENDA, S
    NAKAZONO, Y
    OMATA, T
    TETRAHEDRON, 1991, 47 (32) : 6223 - 6230
  • [7] A new synthetic route to (3R,4S)-3-hydroxy-4-phenylazetidin-2-one as a taxol side chain precursor
    Song, CE
    Lee, SW
    Roh, EJ
    Lee, SG
    Lee, WK
    TETRAHEDRON-ASYMMETRY, 1998, 9 (06) : 983 - 992
  • [8] A new synthetic route to (3R,4S)-@3-@hydroxy-@4-@phenylazetidin-@2-@one as a taxol side chain precursor
    Song, C. E.
    Lee, S. W.
    Roh, E. J.
    Lee, S.
    Tetrahedron: Asymmetry, 9 (06):
  • [9] Kinetic Resolution of (RS)-4-Hydroxy-3-methyl-2-(2′-propynyl)-2-cyclopentenone Acetate by Lipase-Catalyzed Alcoholysis in Organic Media
    Cheng Yongmei
    Wu Jianping
    Xu Gang
    Yang Lirong
    CHINESE JOURNAL OF CATALYSIS, 2010, 31 (02) : 225 - 228
  • [10] A general approach towards 2-substituted 3-hydroxy propanoates; Application to the synthesis of methyl tropinate
    Imogai, H
    Larcheveque, M
    TETRAHEDRON-ASYMMETRY, 1997, 8 (06) : 965 - 972
12345