Stereoselective formal synthesis of the potent proteasome inhibitor:: salinosporamide A

被引：55

作者：

Caubert, Virginie ^{[1
]}

Masse, Julien ^{[1
]}

Retailleau, Pascal ^{[1
]}

Langlois, Nicole ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 03期

关键词：

proteasome inhibitor; salinosporamide A; pyroglutamate; 1,3-dipolar cycloadditions; N-methylnitrone; selective O-benzylation;

D O I：

10.1016/j.tetlet.2006.11.087

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(2R,3S)-alpha-Methylenelactam 3, the key intermediate in Corey's syntheses of salmosporamide A, has been synthesized from (S)-methyl 2-hydroxymethylpyroglutamate through chemoselective O-protection, regio- and stereoselective N-methylnitrone cycloaddition and quaternarization-elimination reactions as the main steps. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：381 / 384

页数：4

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