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Asymmetric synthesis of 2-acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazoles

Journal Article


Abstract


  • 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.

Publication Date


  • 1997

Citation


  • Cliff, M. D., & Pyne, S. G. (1997). Asymmetric synthesis of 2-acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazoles. Journal of Organic Chemistry, 62(4), 1023-1032. doi:10.1021/jo961630f

Scopus Eid


  • 2-s2.0-0030981263

Web Of Science Accession Number


Start Page


  • 1023

End Page


  • 1032

Volume


  • 62

Issue


  • 4

Abstract


  • 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.

Publication Date


  • 1997

Citation


  • Cliff, M. D., & Pyne, S. G. (1997). Asymmetric synthesis of 2-acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazoles. Journal of Organic Chemistry, 62(4), 1023-1032. doi:10.1021/jo961630f

Scopus Eid


  • 2-s2.0-0030981263

Web Of Science Accession Number


Start Page


  • 1023

End Page


  • 1032

Volume


  • 62

Issue


  • 4