ASYMMETRIC-SYNTHESIS OF 2-ACETYL-4(5)-(1,2,4-TRIHYDROXYBUTYL)IMIDAZOLES

Authors
CLIFF MD PYNE SG
Citation
Md. Cliff et Sg. Pyne, ASYMMETRIC-SYNTHESIS OF 2-ACETYL-4(5)-(1,2,4-TRIHYDROXYBUTYL)IMIDAZOLES, Journal of organic chemistry, 60(8), 1995, pp. 2378-2383
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
60
Issue
8
Year of publication
1995
Pages
2378 - 2383
Database
ISI
SICI code
0022-3263(1995)60:8<2378:AO2>2.0.ZU;2-S
Abstract
A method for preparing trihydroxybutyl analogues of the biologically a ctive compound 2-acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazole (THI ) is reported. This method employs a palladium(0)catalyzed coupling of 1-(ethoxymethyl)-4-iodoimidazole (3a) to functionalized vinylstannane 11, 1-alkynylstannane 16, or alkyne 10 to introduce the C-4 imidazole 4-carbon side chain, The 1,2-dihydroxyfunctionality of the butyl side chain was introduced by a Sharpless catalytic asymmetric dihydroxylat ion.