C-GLYCOSIDES .9. STEREOSPECIFIC SYNTHESIS OF C-GLYCOSIDIC SPIROKETAL OF THE PAPULACANDINS

被引:43
作者
CZERNECKI, S
PERLAT, MC
机构
[1] Laboratoire de Chimie des Glucides, Université Pierre et Marie Curie, 75005 Paris, T 74, E6, 4, place Jussieu
关键词
D O I
10.1021/jo00022a014
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of ortho-lithiated triphenylmethyl benzyl ether with perbenzylated D-gluconolactone 1 followed by cyclization by BF3.Et2O provides a new stereospecific synthesis of C-glycosidic spiroketals. The structure of the peracetylated derivative was determined by X-ray diffraction. This methodology is applied to the synthesis of the spiroketal unit of papulacandins.
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页码:6289 / 6292
页数:4
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