STEREOSELECTIVE OXIDATIVE SPIROKETALIZATION OF A C-ARYLGLUCAL DERIVED FROM PALLADIUM-CATALYZED COUPLING - SYNTHESIS OF THE C-ARYLGLUCOSIDE SPIROKETAL NUCLEUS OF THE PAPULACANDINS

被引:60
作者
FRIESEN, RW
STURINO, CF
机构
[1] Department of Chemistry, University of Toronto, Lash Miller Chemical Laboratories, Toronto, Ontario
关键词
D O I
10.1021/jo00310a004
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
: The synthesis of the C-arylglucoside tricyclic spiroketal nucleus of the papulacandins 5b was achieved utilizing two key steps, namely the palladium-catalyzed coupling of the aryl bromide 6 and the stannyl glucal 2 and stereoselective oxidative spiroketalization of the derived C-arylglucal 7. © 1990, American Chemical Society. All rights reserved.
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页码:5808 / 5810
页数:3
相关论文
共 20 条
[1]  
BAERTSCHI SW, 1988, J AM CHEM SOC, V110, P1988
[2]   PAPULACANDIN-B - INHIBITOR OF GLUCAN SYNTHESIS IN YEAST SPHEROPLASTS [J].
BAGULEY, BC ;
ROMMELE, G ;
GRUNER, J ;
WEHRLI, W .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1979, 97 (02) :345-351
[3]  
BRIGL PZ, 1922, Z PHYSL CHEM, V122, P245
[4]   A FULLY SYNTHETIC ROUTE TO THE PAPULACANDINS - STEREOSPECIFIC SPIROACETALIZATION OF A C-1-ARYLATED METHYL GLYCOSIDE [J].
DANISHEFSKY, S ;
PHILLIPS, G ;
CIUFOLINI, M .
CARBOHYDRATE RESEARCH, 1987, 171 :317-327
[5]   THE PREPARATION OF C-ARYLGLYCALS - THE PALLADIUM-CATALYZED COUPLING OF 3,4,6-TRI-O-(TERT-BUTYLDIMETHYLSILYL)-1-(TRIBUTYLSTANNYL)-D-GLUCAL AND ARYL BROMIDES [J].
FRIESEN, RW ;
STURINO, CF .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (09) :2572-2574
[6]   PAPULACANDIN, A NEW ANTIBIOTIC, ACTIVE ESPECIALLY AGAINST YEASTS [J].
GRUNER, J ;
TRAXLER, P .
EXPERIENTIA, 1977, 33 (01) :137-137
[7]  
Hacksell U, 1985, Prog Med Chem, V22, P1, DOI 10.1016/S0079-6468(08)70228-5
[8]   ON THE DIRECT EPOXIDATION OF GLYCALS - APPLICATION OF A REITERATIVE STRATEGY FOR THE SYNTHESIS OF BETA-LINKED OLIGOSACCHARIDES [J].
HALCOMB, RL ;
DANISHEFSKY, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (17) :6661-6666
[9]   FORMATION OF C-GLYCOSIDES BY POLARITY INVERSION AT THE ANOMERIC CENTER [J].
HANESSIAN, S ;
MARTIN, M ;
DESAI, RC .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (12) :926-927
[10]   A CHEMICAL SYNTHESIS OF SUCROSE - A CONFORMATIONAL ANALYSIS OF THE REACTIONS OF 1,2-ANHYDRO-ALPHA-D-GLUCOPYRANOSE TRIACETATE [J].
LEMIEUX, RU ;
HUBER, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (16) :4117-4119