A new procedure for the preparation of β-keto-δ-lactones from sugars and their transformation into glycosyl accepters in disaccharides synthesis

被引：12

作者：

Bartolozzi, A ^{[1
]}

Capozzi, G ^{[1
]}

Menichetti, S ^{[1
]}

Nativi, C ^{[1
]}

机构：

[1] Univ Florence, CNR, Ctr Chim Composti Eterociclici, Dipartimento Chim Organ, I-50121 Florence, Italy

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 03期

关键词：

D O I：

10.1021/ol991176c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Glycals are effective starting materials for the synthesis of enantiopure beta-ketone-delta-lactones, They are easily transformed, through a two-step, one pot reaction, into the corresponding alpha,alpha'-dioxothiones which in turn can be quantitatively trapped with dienophiles in inverse electron-demand [4 + 2] cycloadditions. The reaction of dioxothione 8b with endo and exo glucals allowed the elaboration of a new protocol to prepare 2-thio- or 2-deoxydisaccharides stereoselectively.

引用

页码：251 / 253

页数：3

共 19 条

[1] Regio- and stereoselective synthesis of 4′-thiaspiroacetals from carbohydrates [J].