A total synthesis of epothilones using solid-supported reagents and scavengers

被引:58
作者
Storer, RI [1 ]
Takemoto, T [1 ]
Jackson, PS [1 ]
Ley, SV [1 ]
机构
[1] Univ Cambridge, Chem Lab, Cambridge CB2 1EW, England
关键词
aldol reaction; antitumor agents; natural products; polyketides; polymers;
D O I
10.1002/anie.200351413
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A total synthesis of epothilone C(1) with concomitant formal synthesis of epothilone A is described, using immobilized reagents and scavengers to effect multistep synthetic transformations and purifications.
引用
收藏
页码:2521 / 2525
页数:5
相关论文
共 87 条
[1]   Total synthesis of (-)-epothilone A [J].
Balog, A ;
Meng, DF ;
Kamenecka, T ;
Bertinato, P ;
Su, DS ;
Sorensen, EJ ;
Danishefsky, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (23-24) :2801-2803
[2]  
Balog A, 1998, ANGEW CHEM INT EDIT, V37, P2675, DOI 10.1002/(SICI)1521-3773(19981016)37:19<2675::AID-ANIE2675>3.0.CO
[3]  
2-O
[4]  
Balog A., 1996, Angew. Chem, V108, P2976
[5]  
BALOG A, 1998, ANGEW CHEM, V110, P2821
[6]   Total synthesis of the amaryllidaceae alkaloid (+)-plicamine using solid-supported reagents [J].
Baxendale, IR ;
Ley, SV ;
Nessi, M ;
Piutti, C .
TETRAHEDRON, 2002, 58 (32) :6285-6304
[7]   Stereoselective syntheses of epothilones A and B via directed nitrile oxide cycloaddition [J].
Bode, JW ;
Carreira, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (15) :3611-3612
[8]   Stereoselective syntheses of epothilones A and B via nitrile oxide cycloadditions and related studies [J].
Bode, JW ;
Carreira, EM .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (19) :6410-6424
[9]  
BOLLAG DM, 1995, CANCER RES, V55, P2325
[10]   Development of a polymer bound Wittig reaction and use in multi-step organic synthesis for the overall conversion of alcohols to β-hydroxyamines [J].
Bolli, MH ;
Ley, SV .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (15) :2243-2246