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    Title: Expeditious Synthesis of Tri- and Tetrahydroxyazepanes from d-(−)-Quinic Acid as Potent Glycosidase Inhibitors
    Authors: Shih, Tzenge-lien;Yang, Ru-ying;Li, Shiou-ting;Chiang, Cheng-fan;Lin, Chun-hung
    Contributors: 淡江大學化學學系
    Date: 2007-05-25
    Issue Date: 2009-12-01
    Publisher: Washington: American Chemical Society
    Abstract: Several new stereoisomers of 3,4,6-trihydroxyazepanes and 7-hydroxymethyl-3,4,5-trihydroxyazepanes as well as known 3,4,5-trihydroxyazepanes were synthesized as potent glycosidase inhibitors from D-(-)-quinic acid in an efficient manner. The key step employs dihydroxylation of protected chiral 1,4,5-cyclohex-2-enetriols under RuCl3/NaIO4/phosphate buffer (pH 7) condition, followed by reductive amino cyclization. We found the choice of an appropriate protecting group to C1-OH of chiral 1,4,5-cyclohex-2-enetriols would increase the yields of cyclization. The preliminary biological data indicate some of these azepanes possess potent inhibition against alpha-mannosidase and alpha-fucosidase.
    Relation: Journal of Organic Chemistry 72(11), pp.4258-4261
    DOI: 10.1021/jo070058x
    Appears in Collections:[化學學系暨研究所] 期刊論文

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