The first asymmetric synthesis of (2S,3S,4R)-3-amino-2-hydroxymethyl-4-hydroxypyrrolidine

被引：19

作者：

Curtis, KL ^{[1
]}

Fawcett, J ^{[1
]}

Handa, S ^{[1
]}

机构：

[1] Univ Leicester, Dept Chem, Leicester LE1 7RH, Leics, England

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 32期

基金：

英国工程与自然科学研究理事会;

关键词：

amino pyrrolidine; glycosidase inhibitor; tethered aminohydroxylation;

D O I：

10.1016/j.tetlet.2005.06.025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The novel (2S,3S,4R)-3-amino-2-hydroxymethyl-4-hydroxypyrrolidine 5 has been produced in an efficient synthesis from trans-4-hydroxy-L-proline 8. The key step involves a tethered aminohydroxylation of the alkene 7 to introduce regio- and stereo-selectively the amino alcohol functionality in the resulting products 6 and 13. Subsequent deprotection steps furnish the target molecule 5 as well as several differentially protected analogues. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：5297 / 5300

页数：4

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