C-glycosides to fused polycyclic ethers

被引:94
作者
Allwein, SP [1 ]
Cox, JM [1 ]
Howard, BE [1 ]
Johnson, HWB [1 ]
Rainier, JD [1 ]
机构
[1] Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
基金
美国国家科学基金会; 美国国家卫生研究院;
关键词
C-glycosides; polycyclic ethers; annulation reactions;
D O I
10.1016/S0040-4020(02)00057-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This manuscript describes the synthesis of fused polycyclic ethers from the coupling of C-glycoside forming reactions with ring closing metathesis and acid mediated annulation reactions. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1997 / 2009
页数:13
相关论文
共 63 条
[1]   A CONVENIENT PREPARATION OF ACETONE SOLUTIONS OF DIMETHYLDIOXIRANE [J].
ADAM, W ;
BIALAS, J ;
HADJIARAPOGLOU, L .
CHEMISCHE BERICHTE, 1991, 124 (10) :2377-2377
[2]   TOTAL SYNTHESIS OF HALICHONDRIN-B AND NORHALICHONDRIN-B [J].
AICHER, TD ;
BUSZEK, KR ;
FANG, FG ;
FORSYTH, CJ ;
JUNG, SH ;
KISHI, Y ;
MATELICH, MC ;
SCOLA, PM ;
SPERO, DM ;
YOON, SK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (08) :3162-3164
[3]  
ALLWEIN SP, UNPUB
[4]   SIMPLE DESIGNS FOR THE CONSTRUCTION OF COMPLEX TRANS-FUSED POLYETHER TOXIN FRAMEWORKS - A LINEAR STRATEGY BASED ON ENTROPICALLY FAVORED OXIRANE RING ENLARGEMENT IN EPOXYCYCLOALKENES FOLLOWED BY CARBON-CARBON OR CARBON-OXYGEN BOND-FORMING CYCLIZATIONS [J].
ALVAREZ, E ;
DIAZ, MT ;
PEREZ, R ;
RAVELO, JL ;
REGUEIRO, A ;
VERA, JA ;
ZURITA, D ;
MARTIN, JD .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (10) :2848-2876
[5]  
Bailey JM, 1999, SYNLETT, P132
[6]   STEREOCONTROLLED SYNTHESIS OF C-GLYCOSIDES BY REACTION OF ORGANOCUPRATES WITH PROTECTED 1,2-ANHYDRO SUGARS, AND THEIR TRANSFORMATION INTO 2-DEOXY-C-GLYCOSIDES [J].
BELLOSTA, V ;
CZERNECKI, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (03) :199-200
[7]   The synthesis of some epoxyalkyl beta-C-glycosides as potential inhibitors of beta-glucan hydrolases [J].
Best, WM ;
Ferro, V ;
Harle, J ;
Stick, RV ;
Tilbrook, DMG .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1997, 50 (05) :463-472
[8]   A reiterative synthesis of trans-fused polypyrans via tungsten pentacarbonyl-promoted alkynol endocyclization [J].
Bowman, JL ;
McDonald, FE .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (11) :3680-3682
[9]   ORGANOBORANES .43. A CONVENIENT, HIGHLY EFFICIENT SYNTHESIS OF TRIORGANYLBORANES VIA A MODIFIED ORGANOMETALLIC ROUTE [J].
BROWN, HC ;
RACHERLA, US .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (04) :427-432
[10]   Preparation of C-1 glycals via olefin metathesis.: A convergent and flexible approach to C-glycoside synthesis [J].
Calimente, D ;
Postema, MHD .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (06) :1770-1771