Asymmetric synthesis of 2-acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazoles

被引：25

作者：

Cliff, MD ^{[1
]}

Pyne, SG ^{[1
]}

机构：

[1] UNIV WOLLONGONG,DEPT CHEM,WOLLONGONG,NSW 2522,AUSTRALIA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 04期

关键词：

D O I：

10.1021/jo961630f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for preparing the eight stereoisomers of the biologically active compound (1R,2S,3R)-2-acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazole (THI, 1) is reported. This method employs a palladium(0)-catalyzed coupling of 1-(ethoxymethyl)-4-iodoimidazole (7) to functionalized vinylstannanes (R)- or (S)-12a,b or 13a,b or 1-alkynylstannanes (R)- or (S)-6a,b to introduce the C-4 imidazole four-carbon side chain. The 1,2-dihydroxy functionality of the butyl side chain was introduced by Sharpless catalytic asymmetric dihydroxylation reactions.

引用

页码：1023 / 1032

页数：10

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