ENANTIOSELECTIVE SYNTHESIS OF BOTH ENANTIOMERS OF ETODOLAC VIA A LIPASE-CATALYZED KINETIC RESOLUTION

被引：4
|
作者：
Akai, Shuji [1 ]
Nemoto, Hiroyuki [1 ]
Egi, Masahiro [1 ]
机构：
[1] Univ Shizuoka, Sch Pharmaceut Sci, Suruga Ku, Shizuoka 4228526, Japan
来源：
HETEROCYCLES | 2008年 / 76卷 / 02期
关键词：
Kinetic Resolution; Lipase; Indole; Oxidation; Chemoselective Reaction;
D O I：
10.3987/COM-08-S(N)118
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The efficient preparation of both enantiomers of etodolac 1 was achieved by the lipase-catalyzed kinetic resolution of the racemic primary alcohol (+/-)-2 followed by chemoselective oxidation.
引用
收藏
页码：1537 / 1547
页数：11
相关论文
共 50 条
  • [21] Dynamic Kinetic Resolution of 2-Hydroxybiaryl Atropisomers via Lipase-Catalyzed Enantioselective O-Acylation
    Dhiman, Neha
    Moustafa, Gamal A. I.
    Kasama, Kengo
    Aoyama, Hiroshi
    Kanomata, Kyohei
    Groeger, Harald
    Akai, Shuji
    CHEMCATCHEM, 2024, 16 (21)
  • [22] Lipase-catalyzed dynamic kinetic resolution of hemiaminals
    Sharfuddin, M
    Narumi, A
    Iwai, Y
    Miyazawa, K
    Yamada, S
    Kakuchi, T
    Kaga, H
    TETRAHEDRON-ASYMMETRY, 2003, 14 (11) : 1581 - 1585
  • [23] Resolution of secondary alcohols via Carica papaya lipase-catalyzed enantioselective acylation
    Miyazawa, Toshifumi
    Houhashi, Mika
    Inoue, Yusuke
    Murashima, Takashi
    Yamada, Takashi
    BIOTECHNOLOGY LETTERS, 2008, 30 (10) : 1783 - 1787
  • [24] Resolution of secondary alcohols via Carica papaya lipase-catalyzed enantioselective acylation
    Toshifumi Miyazawa
    Mika Houhashi
    Yusuke Inoue
    Takashi Murashima
    Takashi Yamada
    Biotechnology Letters, 2008, 30 : 1783 - 1787
  • [25] Lipase-Catalyzed Highly Enantioselective Kinetic Resolution of Boron-Containing Chiral Alcohols
    Andrade, Leandro H.
    Barcellos, Thiago
    ORGANIC LETTERS, 2009, 11 (14) : 3052 - 3055
  • [26] Resolution of racemic rhododendrol by lipase-catalyzed enantioselective acetylation
    Yuasa, Y
    Shibuya, S
    Yuasa, Y
    SYNTHETIC COMMUNICATIONS, 2003, 33 (09) : 1469 - 1475
  • [27] Highly enantioselective lipase-catalyzed kinetic resolution of 2-silyloxy-1-propanol
    Kawanami, Y
    Itoh, K
    CHEMISTRY LETTERS, 2005, 34 (05) : 682 - 683
  • [28] A FACILE SYNTHESIS OF N-PROTECTED STATINE AND ANALOGS VIA A LIPASE-CATALYZED KINETIC RESOLUTION
    BANZIGER, M
    MCGARRITY, JF
    MEUL, T
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15): : 4010 - 4012
  • [29] Synthesis of chiral oxazolidinone derivatives through lipase-catalyzed kinetic resolution
    Zhang, Yan
    Zhang, Yang
    Ren, Yansong
    Ramstrom, Olof
    JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2015, 122 : 29 - 34
  • [30] Preparation of Passion Fruit-Typical 2-Alkyl Ester Enantiomers via Lipase-Catalyzed Kinetic Resolution
    Strohalm, Hedwig
    Dold, Susanne
    Pendzialek, Kathrin
    Weiher, Monika
    Engel, Karl-Heinz
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2010, 58 (10) : 6328 - 6333
12345