TOTALLY CHEMICAL SYNTHESIS OF AZASUGARS VIA THIAZOLE INTERMEDIATES - STEREODIVERGENT ROUTES TO (-)-NOJIRIMYCIN, (-)-MANNOJIRIMYCIN AND THEIR 3-DEOXY DERIVATIVES FROM SERINE

被引：58
作者：
DONDONI, A
MERINO, P
PERRONE, D
机构：
[1] Laboratorio di Chimica Organica, Dipartimento di Chimica, Università, Ferrara
来源：
TETRAHEDRON | 1993年 / 49卷 / 14期
关键词：
THIAZOLE; AZASUGARS; NOJIRIMYCIN; MANNOJIRIMYCIN; GLYCOSIDASE INHIBITORS;
D O I：
10.1016/S0040-4020(01)80389-6
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of the (-)-antipodes of the natural products nojirimycin (+)-1 and mannojirimycin (+)-2 has been carried out by stereocontrolled reduction of the thiazole ketone 7 as a common key intermediate. This ketone was in turn obtained from the L-serine derived aldehyde 3 by two convergent routes involving carbonylolefination and dihydroxylation processes. Moreover, 3-deoxy derivatives of (-)-1 and (-)-2 have been prepared from 3 and the lithium enolate of 2-acetylthiazole followed by stereocontrolled reduction of the resultant aldol.
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页码：2939 / 2956
页数：18
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