Stereoselective syntheses of epothilones A and B via directed nitrile oxide cycloaddition

被引:139
作者
Bode, JW [1 ]
Carreira, EM [1 ]
机构
[1] Swiss Fed Inst Technol, Organ Chem Lab, CH-8092 Zurich, Switzerland
关键词
D O I
10.1021/ja0155635
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
引用
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页码:3611 / 3612
页数:2
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共 29 条
[1]  
Altmann KH, 2000, CHIMIA, V54, P612
[2]   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
[3]   HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS [J].
BLANCHETTE, MA ;
CHOY, W ;
DAVIS, JT ;
ESSENFELD, AP ;
MASAMUNE, S ;
ROUSH, WR ;
SAKAI, T .
TETRAHEDRON LETTERS, 1984, 25 (21) :2183-2186
[4]   A novel application of a Pd(0)-catalyzed nucleophilic substitution reaction to the regio- and stereoselective synthesis of lactam analogues of the epothilone natural products [J].
Borzilleri, RM ;
Zheng, XP ;
Schmidt, RJ ;
Johnson, JA ;
Kim, SH ;
DiMarco, JD ;
Fairchild, CR ;
Gougoutas, JZ ;
Lee, FYF ;
Long, BH ;
Vite, GD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (37) :8890-8897
[5]   Enantioselective addition of 2-methyl-3-butyn-2-ol to aldehydes:: Preparation of 3-hydroxy-1-butynes [J].
Boyall, D ;
López, F ;
Sasaki, H ;
Frantz, D ;
Carreira, EM .
ORGANIC LETTERS, 2000, 2 (26) :4233-4236
[6]   A NOVEL METHOD FOR THE INSITU GENERATION OF ALKOXYDIALKYLBORANES AND THEIR USE IN THE SELECTIVE PREPARATION OF 1,3-SYN DIOLS [J].
CHEN, KM ;
GUNDERSON, KG ;
HARDTMANN, GE ;
PRASAD, K ;
REPIC, O ;
SHAPIRO, MJ .
CHEMISTRY LETTERS, 1987, (10) :1923-1926
[7]   Cleavage of N-O bonds promoted by samarium diiodide: Reduction of free or N-acylated O-alkylhydroxylamines [J].
Chiara, JL ;
Destabel, C ;
Gallego, P ;
MarcoContelles, J .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (01) :359-360
[8]   NUCLEOPHILIC ADDITIONS TO AND REDUCTIONS OF 5-FORMYL-2-ISOXAZOLINE AND 5-ACYL-2-ISOXAZOLINE (4,5-DIHYDROISOXAZOLES) - A STEREOSELECTIVE ROUTE TO BETA,GAMMA-DIHYDROXY KETONES [J].
CURRAN, DP ;
ZHANG, JC .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (11) :2613-2625
[9]   PREPARATION AND USE OF TETRA-NORMAL-BUTYLAMMONIUM PER-RUTHENATE (TBAP REAGENT) AND TETRA-NORMAL-PROPYLAMMONIUM PER-RUTHENATE (TPAP REAGENT) AS NEW CATALYTIC OXIDANTS FOR ALCOHOLS [J].
GRIFFITH, WP ;
LEY, SV ;
WHITCOMBE, GP ;
WHITE, AD .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (21) :1625-1627
[10]   REACTIONS WITH ALPHA,BETA-UNSATURATED NITRILE OXIDES - SYNTHETIC STUDIES IN THE TERPENE FIELD - SYNTHESIS OF TAGETONES, OCIMENONES, DEODARONE AND ATLANTONE [J].
ISAGER, P ;
THOMSEN, I ;
TORSSELL, KBG .
ACTA CHEMICA SCANDINAVICA, 1990, 44 (08) :806-813