regioselectivity in the ring opening of epoxides for the synthesis of aminocyclitols from d-(-)-quinic acid区域选择性的合成环氧化合物开环的aminocyclitols从d -(-)奎尼酸.pdfVIP

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regioselectivity in the ring opening of epoxides for the synthesis of aminocyclitols from d-(-)-quinic acid区域选择性的合成环氧化合物开环的aminocyclitols从d -(-)奎尼酸.pdf

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regioselectivity in the ring opening of epoxides for the synthesis of aminocyclitols from d-(-)-quinic acid区域选择性的合成环氧化合物开环的aminocyclitols从d -(-)奎尼酸

Molecules 2012, 17, 4498-4507; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Regioselectivity in the Ring Opening of Epoxides for the Synthesis of Aminocyclitols from D-()-Quinic Acid Tzenge-Lien Shih * and Shu-Yu Yang Department of Chemistry, Tamkang University, No151 Yingzhuan Rd, 25137 Tamsui Dist., New Taipei City, Taiwan; E-Mail: 699180088@.tw * Author to whom correspondence should be addressed; E-Mail: tlshih@.tw; Tel./Fax: +886-2-8631-5024. Received: 26 March 2012; in revised form: 9 April 2012 / Accepted: 10 April 2012 / Published: 16 April 2012 Abstract: Efficient syntheses of four aminocyclitols are reported. Each synthesis is accomplished in eight steps starting from D-()-quinic acid. The key step involves a highly regioselective ring opening of epoxides by sodium azide. Keywords: aminocyclitols; epoxides; glycosidase inhibitors; D-()-quinic acid; regioselective ring opening 1. Introduction Aminocyclitols, also known as aminocarbasugars [1], contain at least one amino or substituted amino moiety in the cyclitols (polyhydroxylated cycloalkanes) [2]. Many natural and synthetic products containing aminocyclitol scaffolds have shown a variety of biological activities [3,4], such as, valienamine [5], pancratistatin [6], oseltamivir [7], and voglibose [4] (Figure 1). The synthesis of biological active aminocyclitols and assessment of their structure and activity