Synthesis of 1,6-dideoxynojirimycin, 1,6-dideoxy-D-allo-nojirimycin, and 1,6-dideoxy-D-gulo-nojirimycin via asymmetric hetero-Diels-Alder reactions

被引：25

作者：

Defoin, A

Sarazin, H

Streith, J

机构：

[1] Ecl. Natl. Sup. de Chim. de Mulhouse, Université de Haute-Alsace, F-68093 Mulhouse Cedex, 3, rue Alfred Werner

来源：

HELVETICA CHIMICA ACTA | 1996年 / 79卷 / 02期

关键词：

D O I：

10.1002/hlca.19960790223

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Asymmetric Diels-Alder reaction of sorbaldehyde O-methyloxime 1d with chiral chloronitroso derivative 2 of D-mannose, followed by osmylation of the primary cycloadduct, led to diol 6a with excellent enantioselectivity (ee > 99%; Scheme 1). Catalytic hydrogenolysis of 6a gave 1,6-dideoxy-D-allo-nojirimycin (7a). Nucleophilic ring opening of cyclic sulfate 8 allowed a straightforwvard synthesis of 1,6-dideoxy-D-nojirimycin (11) and of 1,6-dideoxy-D-gulo-nojirimycin (12; Scheme 2).

引用

页码：560 / 567

页数：8

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