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

Journal Article


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.

Publication Date


  • 1995

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

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.

Publication Date


  • 1995

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

Scopus Eid


  • 2-s2.0-0029028479

Web Of Science Accession Number


Start Page


  • 2378

End Page


  • 2383

Volume


  • 60

Issue


  • 8