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.


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.



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