Synthesis of thiazole analogues of the immunosuppressive agent (1R,2S,3R)-2-acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazole

Authors

George R. Jeoffreys, University of Wollongong
Alison T. Ung, University of WollongongFollow
Stephen G. Pyne, University of WollongongFollow
Brian W. Skelton, University of Western Australia
Allan H. White, University of Western Australia

Publication Details

Jeoffreys, G. R., Ung, A. T., Pyne, S. G., Skelton, B. W. & White, A. H. (1999). Synthesis of thiazole analogues of the immunosuppressive agent (1R,2S,3R)-2-acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazole, Journal of the Chemical Society, Perkin Transactions 1, (16), 2281-2291.

Abstract

The synthesis of four of the diastereoisomers of 2-acetyl-5-(1,2,3,4-tetrahydroxybutyl)thiazole and two of the diastereoisomers of 2-acetyl-5-(1,2,3,4,5-pentahydroxypentyl)thiazole and 2-acetyl-4-(1,2,3,4,5-pentahydroxypentyl)thiazole are reported. These syntheses involve the condensation of 5- or 4-metallated 2-(1,1-dimethoxyethyl)thiazoles with 2,3-O-isopropylidene-D-erythrono-1,4-lactone or 5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-D-ribonolactone followed by reductive ring-opening of the resulting lactols. The stereochemistries and structures of some key compounds have been determined by single crystal X-ray structural analysis.