Synthesis of dihydroxylated prolines and iminocyclitols from five-membered endocyclic enecarbamates.: Total synthesis of the potent glycosidase inhibitor (2R,3R,4R,5R)-2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine (DMDP)

被引：45

作者：

Garcia, ALL ^{[1
]}

Correia, CRD ^{[1
]}

机构：

[1] Univ Estadual Campinas, Inst Quim, BR-13083970 Campinas, SP, Brazil

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 08期

基金：

巴西圣保罗研究基金会;

关键词：

D O I：

10.1016/S0040-4039(03)00017-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

cis- and trans-3,4-Dihydroxylated prolines and the iminocyclitol 1,4-dideoxy-1,4-imino ribitol were synthesized employing a strategy involving the Heck arylation of five-membered endocyclic enecarbarnates with aryldiazonium salts followed by oxidative cleavage of the electron-rich aromatic ring. The total synthesis of the potent alpha- and beta-glucosidase inhibitor (2R,3R,4R,5R)-2,5-hydroxymethyl-3,4-dihydroxypyrrolidine (DMDP) was also achieved by the same strategy in ten steps from a chiral five-membered enecarbamate in 12% overall yield. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：1553 / 1557

页数：5

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