STEREOSELECTIVE TEMPLATE-DIRECTED C-GLYCOSIDATION - SYNTHESIS OF 5-MEMBERED OXYGEN HETEROCYCLES VIA CATION-MEDIATED INTRAMOLECULAR CYCLIZATION REACTIONS

被引：13

作者：

CRAIG, D ^{[1
]}

PENNINGTON, MW ^{[1
]}

WARNER, P ^{[1
]}

机构：

[1] ZENECA PHARMACEUT,MACCLESFIELD SK10 4TG,CHESHIRE,ENGLAND

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 52期

关键词：

D O I：

10.1016/S0040-4039(00)61379-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Construction of 5-membered oxygen heterocycles by intramolecular template-directed C-glycosidation is described. Alkylation of thioglycoside 5 with enone 6 followed by enol etherification gave cyclization substrates 8. Compound 8a underwent silver(I) trifluoromethanesulfonate-mediated ring-closure to give a 1.7:1 mixture of 9 alpha and 9 beta; isomer 8s gave an 8.5:1 ratio. Some derivatization reactions of the bicyclic products are described.

引用

页码：8539 / 8542

页数：4

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