General entries to C-aryl glycosides.: Formal synthesis of galtamycinone

被引:46
作者
Apsel, B [1 ]
Bender, JA [1 ]
Escobar, M [1 ]
Kaelin, DE [1 ]
Lopez, OD [1 ]
Martin, SF [1 ]
机构
[1] Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA
基金
美国国家卫生研究院;
关键词
C-aryl glycosides; Diels-Alder reaction; palladium-catalyzed ring openings;
D O I
10.1016/S0040-4039(02)02666-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Utilizing a general entry we had developed for the synthesis of C-aryl glycosides, we have prepared the juglone derivatives 18-20 as well as the juglone precursor 13. Because 19 had been previously converted in two steps by Suzuki into galtamycinone (1), its preparation constitutes a total synthesis of 1. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1075 / 1077
页数:3
相关论文
共 29 条
[1]  
BELITSKAYA LD, 1984, ZH ORG KHIM+, V20, P1920
[2]   Synthesis of a 2-deoxyglucosyl analogue of medermycin [J].
Brimble, MA ;
Brenstrum, TJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (14) :1624-1634
[3]   SYNTHESIS OF THE NAPHTHACENEQUINONE SS-228R [J].
CAMERON, DW ;
FEUTRILL, GI ;
GIBSON, CL ;
READ, RW .
TETRAHEDRON LETTERS, 1985, 26 (32) :3887-3888
[4]   SYNTHESIS OF NAPHTHACENEQUINONES BY CYCLOADDITION AND DEOXYGENATION METHODOLOGY - SYNTHESIS OF SS-228R [J].
CAMERON, DW ;
FEUTRILL, GI ;
GIBSON, CL .
TETRAHEDRON LETTERS, 1993, 34 (38) :6109-6110
[5]   Recent advances in stereoselective C-glycoside synthesis [J].
Du, YG ;
Linhardt, RJ ;
Vlahov, IR .
TETRAHEDRON, 1998, 54 (34) :9913-9959
[6]   PALLADIUM-CATALYZED STEREOSELECTIVE REDUCTIVE COUPLING REACTIONS OF ORGANIC HALIDES WITH 7-HETEROATOM NORBORNADIENES [J].
DUAN, JP ;
CHENG, CH .
TETRAHEDRON LETTERS, 1993, 34 (25) :4019-4022
[7]   SYNTHESIS OF C-GLYCOPYRANOSYL COMPOUNDS BY A PALLADIUM-CATALYZED COUPLING REACTION OF 1-TRIBUTYLSTANNYL-D-GLUCALS WITH ORGANIC HALIDES [J].
DUBOIS, E ;
BEAU, JM .
CARBOHYDRATE RESEARCH, 1992, 228 (01) :103-120
[8]   Nickel-catalyzed highly stereoselective ring opening of 7-oxa- and azanorbornenes with organic halides [J].
Feng, CC ;
Nandi, M ;
Sambaiah, T ;
Cheng, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) :3538-3543
[9]   THE PREPARATION OF C-ARYL GLUCALS VIA PALLADIUM-CATALYZED CROSS-COUPLING METHODS [J].
FRIESEN, RW ;
LOO, RW ;
STURINO, CF .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (05) :1262-1272
[10]  
Fuganti C, 1999, SYNLETT, P1241