Abstract
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A method for preparing trihydroxybutyl analogues of the biologically active compound 2-acetyl-4(5)-(1, 2, 3, 4-tetrahydroxybutyl)imidazole (THI) is reported. This method employs a palladium(0)-catalyzed coupling of l-(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 dihy droxylation. �� 1995, American Chemical Society. All rights reserved.