A NEW SYNTHETIC ROUTE TO CHIRAL, MULTIPLY FUNCTIONALIZED CYCLOPENTANE RINGS

被引:11
作者
CONTELLES, JM
RUIZ, P
SANCHEZ, B
JIMENO, ML
机构
关键词
D O I
10.1016/S0040-4039(00)79149-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The tributyltin hydride mediated free radical cyclization of sugar derivatives 4-6 gives the annulated furanoses 9-11 in good yield and high diastereoselectivity. This protocol is a new synthetic route for the preparation of complex cyclopentanoid molecules.
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页码:5261 / 5264
页数:4
相关论文
共 30 条
[1]   RADICAL CYCLIZATION ON CARBOHYDRATE PYRANOSIDES - A CONTROLLED FORMATION OF FUNCTIONALIZED RING-FUSED BICYCLIC ACETALS [J].
AUDIN, C ;
LANCELIN, JM ;
BEAU, JM .
TETRAHEDRON LETTERS, 1988, 29 (30) :3691-3694
[2]  
BARTLETT PA, 1988, J AM CHEM SOC, V110, P1638
[3]   REGIO-SELECTIVITY AND STEREO-SELECTIVITY OF ALKENYL RADICAL RING-CLOSURE - A THEORETICAL-STUDY [J].
BECKWITH, ALJ ;
SCHIESSER, CH .
TETRAHEDRON, 1985, 41 (19) :3925-3941
[4]  
BIKWAH A, 1989, J CHEM SOC CHEM COMM, P1160
[5]  
Bindra J. S., 1977, PROSTAGLANDIN SYNTHE
[6]  
Giese B., 1986, RADICALS ORGANIC SYN
[7]  
HART DJ, 1981, TETRAHEDRON LETT, V26, P3749
[8]   CYCLOPENTANE-ANNELATED PYRANOSIDES - A NEW APPROACH TO CHIRAL IRIDOID SYNTHESIS [J].
HASHIMOTO, H ;
FURUICHI, K ;
MIWA, T .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (13) :1002-1003
[9]  
HASNOOT CAG, 1980, TETRAHEDRON, V36, P2783
[10]   ELECTRON-SPIN-RESONANCE SPECTROSCOPIC INVESTIGATION OF CARBOHYDRATE RADICALS .3. CONFORMATION IN DEOXYPYRANOSAN-2-YL, DEOXYPYRANOSAN-3-YL, AND DEOXYPYRANOSAN-4-YL RADICALS [J].
KORTH, HG ;
SUSTMANN, R ;
GRONINGER, KS ;
WITZEL, T ;
GIESE, B .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1986, (09) :1461-1464