Flexibility in the partial reduction of 2,5-disubstituted pyrroles: Application to the synthesis of DMDP

被引：53

作者：

Donohoe, TJ

Headley, CE

Cousins, RPC

Cowley, A

机构：

[1] Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England

[2] Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England

[3] GlaxoSmithKline, Med Res Ctr, Stevenage SG1 2NY, Herts, England

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 07期

关键词：

D O I：

10.1021/ol027504h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHIC] The partial reduction of electron-deficient 2,5-disubstituted pyrroles has been developed into a flexible procedure that gives control of relative stereochemistry by variation of the reduction conditions. After the reaction, the pyrroline products were dihydroxylated at C-3,4 to give either the cis or trans isomers; this flexibility means that a variety of polyhydroxylated pyrrolidines can be prepared in a short sequence. Finally, this method was applied to a synthesis of the naturally occurring glycosidase inhibitor DMDP.

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页码：999 / 1002

页数：4

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