Template-directed intramolecular C-glycosidation. Stereoselective synthesis of bicyclic ketooxetanes from anomeric sulfones

被引:15
作者
Craig, D [1 ]
Tierney, JP [1 ]
Williamson, C [1 ]
机构
[1] GLAXO RES & DEV LTD,GREENFORD UB6 0HE,MIDDX,ENGLAND
关键词
D O I
10.1016/S0040-4039(97)00808-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Lewis acid-mediated cyclisations of sugar-derived anomeric sulfone-enol ethers 5 and 6 to give respectively the bicyclic ketooxetanes 11/12 and 16/17 are reported. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:4153 / 4156
页数:4
相关论文
共 13 条
[1]   USE OF 2-PHENYLSULFONYL CYCLIC ETHERS IN THE PREPARATION OF TETRAHYDROPYRAN AND TETRAHYDROFURAN ACETALS AND IN SOME GLYCOSIDATION REACTIONS [J].
BROWN, DS ;
LEY, SV ;
VILE, S ;
THOMPSON, M .
TETRAHEDRON, 1991, 47 (07) :1329-1342
[2]   STEREOSELECTIVE TEMPLATE-DIRECTED C-GLYCOSIDATION - SYNTHESIS OF 5-MEMBERED OXYGEN HETEROCYCLES VIA CATION-MEDIATED INTRAMOLECULAR CYCLIZATION REACTIONS [J].
CRAIG, D ;
PENNINGTON, MW ;
WARNER, P .
TETRAHEDRON LETTERS, 1993, 34 (52) :8539-8542
[3]   STEREOSELECTIVE TEMPLATE-DIRECTED C-GLYCOSIDATION - SILVER(I)-MEDIATED INTRAMOLECULAR REACTIONS OF (2-PYRIDYLTHIO)GLYCOSIDIC SILYL ENOL ETHERS [J].
CRAIG, D ;
MUNASINGHE, VRN .
TETRAHEDRON LETTERS, 1992, 33 (05) :663-666
[5]  
CRAIG D, 1995, TETRAHEDRON LETT, V36, P5815
[6]  
DYATKINA NB, 1984, SYNTHESIS-STUTTGART, P961
[7]  
EMDE H, 1982, SYNTHESIS-STUTTGART, P1
[9]   INTRAMOLECULAR REACTIONS OF 2-O-ORGANOSILYL GLYCOSIDES - HIGHLY STEREOSELECTIVE SYNTHESIS OF C-FURANOSIDES [J].
MARTIN, OR ;
RAO, SP ;
KURZ, KG ;
ELSHENAWY, HA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (26) :8698-8700
[10]   TOTAL SYNTHESIS OF NATURAL (+)-SESBANIMIDE-A AND (-)-SESBANIMIDE-B [J].
MATSUDA, F ;
TERASHIMA, S .
TETRAHEDRON, 1988, 44 (15) :4721-4736