Improved synthesis and preparative scale resolution of racemic monastrol

被引：84

作者：

Dondoni, A ^{[1
]}

Massi, A ^{[1
]}

Sabbatini, S ^{[1
]}

机构：

[1] Univ Ferrara, Dipartmento Chim, Chim Organ Lab, I-44100 Ferrara, Italy

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 34期

关键词：

multicomponent reaction; Biginelli reaction; 3,4-dihydropyrimidine-2-thione; monastrol;

D O I：

10.1016/S0040-4039(02)01269-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Yb(OTf)(3) catalyzed Biginelli cyclocondensation reaction of 3-hydroxybenzaldehyde, ethyl acetoacetate and thiourea afforded the corresponding dihydropyrimidine-2-thione, called monastrol, in 95% isolated yield. The chiral resolution of racemic monastrol, a mitosis blocker by kinesin Eg5 inhibition, was carried out on a preparative scale (ca. 100 mg) through diastereomeric N-3 ribofuranosyl amides. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：5913 / 5916

页数：4

共 11 条

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