Enantiospecific Syntheses of Valiolamine and its (1R), (2R), (1R, 2R) Diastereomers from (−)-Quinic Acid


  • This work was supported by the RGC Earmarked Grant (CUHK69/92E).


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Applicable also for other pseudosugars, the simple reaction sequence for the preparation of α-D-glucosidase inhibitors valiolamine (1) and its three diastereoisomers starts with 1,3,4,5-tetrahydroxycyclohexanecarboxylic acid (quinic acid). Glycosidase inhibitors like 1 are used as chemotherapeutics, for example, against HIV.