Formal synthesis of valienamine using ring-closing metathesis

被引：22

作者：

Cumpstey, I ^{[1
]}

机构：

[1] Univ Stockholm, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 37期

关键词：

valienamine; ring-closing metathesis; selective protection; glucosidase inhibitors;

D O I：

10.1016/j.tetlet.2005.07.054

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1R,2S,3S,4R)-2,3,4-Tri-O-benzyl-5-(benzyloxymethyl)-cyclohex-5-ene-l,2,3,4-tetrol, a precursor of the cc-glucosidase inhibitor, valienamine, was synthesised in eight steps from tetrabenzyl glucose. The key steps were the selective protection of an open-chain diol, and the formation of the cyclohexene ring by ring-closing metathesis with the trisubstituted olefin of valienamine correctly in place. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：6257 / 6259

页数：3

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