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
收藏
页码：1023 / 1032
页数：10
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