Regioselective Baeyer-Villiger lactonization of 2-substituted pyrrolidin-4-one. Synthesis of statine

被引：15

作者：

Chang, Meng-Yang ^{[1
]}

Kung, Yung-Hua

Chen, Shui-Tein

机构：

[1] Natl Univ Kaohsiung, Dept Appl Chem, Kaohsiung 811, Taiwan

[2] Acad Sinica, Inst Biol Chem, Taipei 115, Taiwan

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 28期

关键词：

trans-(2S; 4R)-4-hydroxyproline; prolinol; 1,3-amino alcohol; regio selectivity; Baeyer-Villiger lactonization; tetrahydro-1,3oxazin-6-one; statine;

D O I：

10.1016/j.tetlet.2006.05.027

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nine 2-substituted pyrrolidin-4-ones 4a-i were obtained via a series of functional group transformation of known prolinol 5 by facile six kinds of methodologies. The target structure of 1,3-amino alcohols 2a-i was constructed in the regioselective Baeyer-Villiger lactonization of ketones 4a-i and reduction of the resulting 4-substituted tetrahydro-1,3-oxazin-6-ones 3a-i. A new and straightforward synthesis of (3S,4S)-statine (6) has been established starting from trans-(2S,4R)-4-hydroxyproline (1). (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：4865 / 4870

页数：6

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