Asymmetric Synthesis of 2-Acetyl-4(5)-(l, 2, 4-trihydroxybutyl)imidazoles

Citation

• Cliff, M. D., & Pyne, S. G. (1995). Asymmetric Synthesis of 2-Acetyl-4(5)-(l, 2, 4-trihydroxybutyl)imidazoles. Journal of Organic Chemistry, 60(8), 2378-2383. doi:10.1021/jo00113a016

Digital Object Identifier (doi)

• 10.1021/jo00113a016

Scopus Eid

• 2-s2.0-0029028479

Web Of Science Accession Number

Start Page

• 2378

End Page

• 2383

Volume

• 60

Issue

• 8

Abstract

• 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.

UOW Authors

•   Pyne, Stephen

Publication Date

• 1995

Publisher

• American Chemical Society (ACS) 

Published In

• Journal of Organic Chemistry  Journal

Citation

• Cliff, M. D., & Pyne, S. G. (1995). Asymmetric Synthesis of 2-Acetyl-4(5)-(l, 2, 4-trihydroxybutyl)imidazoles. Journal of Organic Chemistry, 60(8), 2378-2383. doi:10.1021/jo00113a016

Digital Object Identifier (doi)

• 10.1021/jo00113a016

Scopus Eid

• 2-s2.0-0029028479

Web Of Science Accession Number

Start Page

• 2378

End Page

• 2383

Volume

• 60

Issue

• 8