Multi-step application of immobilized reagents and scavengers: A total synthesis of epothilone C

被引:70
作者
Storer, RI
Takemoto, T
Jackson, PS
Brown, DS
Baxendale, IR
Ley, SV
机构
[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
[2] AstraZeneca, Mereside SK10 4TG, Cheshire, England
关键词
aldol reaction; antitumor agents; immobilized reagents; polyketides; polymers;
D O I
10.1002/chem.200305669
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The total synthesis of the cytotoxic antitumour natural product epothilone C has provided a stage for the exploitation and further development of immobilized reagent methods. A stereoselective convergent synthetic strategy was applied, incorporating polymer-supported reagents, catalysts, scavengers and catch-and-release techniques to avoid frequent aqueous work-up and chromatographic purification.
引用
收藏
页码:2529 / 2547
页数:19
相关论文
共 133 条
  • [1] ADAMS BA, 1935, J SOC CHEM IND LOND, P54
  • [2] Chiral synthetic block based on (R)-pantolactone
    Akbutina, FA
    Sadretdinov, IF
    Selezneva, NK
    Miftakhov, MS
    [J]. MENDELEEV COMMUNICATIONS, 2003, (03) : 151 - 152
  • [3] Total synthesis of (-)-epothilone A
    Balog, A
    Meng, DF
    Kamenecka, T
    Bertinato, P
    Su, DS
    Sorensen, EJ
    Danishefsky, S
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (23-24): : 2801 - 2803
  • [4] Balog A, 1998, ANGEW CHEM INT EDIT, V37, P2675, DOI 10.1002/(SICI)1521-3773(19981016)37:19<2675::AID-ANIE2675>3.0.CO
  • [5] 2-O
  • [6] Balog A., 1996, Angew. Chem, V108, P2976
  • [7] BALOG A, 1998, ANGEW CHEM, V110, P2821
  • [8] Polymer-supported reagents for multi-step organic synthesis: Application to the synthesis of sildenafil
    Baxendale, IR
    Ley, SV
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (17) : 1983 - 1986
  • [9] A concise synthesis of carpanone using solid-supported reagents and scavengers
    Baxendale, IR
    Lee, AL
    Ley, SV
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (16): : 1850 - 1857
  • [10] Baxendale IR, 2002, ANGEW CHEM INT EDIT, V41, P2194, DOI 10.1002/1521-3773(20020617)41:12<2194::AID-ANIE2194>3.0.CO