Asymmetric synthesis of 1-deoxynojirimycin and its congeners from a common chiral building block

被引：75

作者：

Takahata, H

Banba, Y

Sasatani, M

Nemoto, H

Kato, A

Adachi, I ^{[1
]}

机构：

[1] Tohoku Pharmaceut Univ, Fac Pharmaceut Sci, Sendai, Miyagi 9818558, Japan

[2] Toyama Med & Pharmaceut Univ, Fac Pharmaceut Sci, Toyama 9300194, Japan

[3] Toyama Med & Pharmaceut Univ, Dept Hosp Pharm, Toyama 9300194, Japan

来源：

TETRAHEDRON | 2004年 / 60卷 / 37期

关键词：

iminosugars; garner aldehyde; asymmetric synthesis;

D O I：

10.1016/j.tet.2004.06.112

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new, promising chiral building block 9 for the synthesis of 1-deoxy-4,5-trans-oriented azasugars such as 1-deoxynojirimycin (1) was prepared in only four steps from the Garner aldehyde 10 using catalytic ring-closing metathesis (RCM) for the construction of the piperidine ring. In practical test, the first synthesis of all four isomers (1 and 6-8) of trans-4,5-orientated 1-deoxyiminosugars using 9 as a common chiral building block was demonstrated. (C) 2004 Elsevier Ltd. All rights reserved.

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页码：8199 / 8205

页数：7

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