Expeditious Synthesis of Tri- and Tetrahydroxyazepanes from D-(-)-Quinic Acid as Potent Glycosidase Inhibitors

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• 作者：Tzenge-Lien Shih ; Ru-Ying Yang ; Shiou-Ting Li ; Cheng-Fan Chiang ; Chun-Hung Lin
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：May 25, 2007
• 年：2007
• 卷：72
• 期：11
• 页码：4258 - 4261
• 全文大小：104K
• 年卷期：v.72,no.11(May 25, 2007)
• ISSN：1520-6904

文摘

Several new stereoisomers of 3,4,6-trihydroxyazepanes and7-hydroxymethyl-3,4,5-trihydroxyazepanes as well as known3,4,5-trihydroxyazepanes were synthesized as potent glycosidase inhibitors from D-(-)-quinic acid in an efficientmanner. The key step employs dihydroxylation of protectedchiral 1,4,5-cyclohex-2-enetriols under RuCl₃/NaIO₄/phosphate buffer (pH 7) condition, followed by reductive aminocyclization. We found the choice of an appropriate protectinggroup to C1-OH of chiral 1,4,5-cyclohex-2-enetriols wouldincrease the yields of cyclization. The preliminary biologicaldata indicate some of these azepanes possess potent inhibitionagainst -mannosidase and -fucosidase.