期刊
TETRAHEDRON LETTERS
卷 45, 期 39, 页码 7239-7242出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2004.08.030
关键词
phytosphingosine; regioselective asymmetric aminohydroxylation; olefin cross metathesis; oxazine
Use of MsCl/Et3N was proven to provide a convenient synthetic tool for the stereochemical intercoversion of the hydroxyl group in N-acetyl 1,3-aminoalcohols. Thus, under these conditions, the alcohols 4 and 6 smoothly converted to the oxazines 5 and 7, respectively, which were hydrolyzed to generate the corresponding inverted alcohols 6 and 4 in one pot. Further elaboration of 4 and 6 led to the efficient asymmetric synthesis of N-acetyl L-xylo- and L-arabino-phytosphingosines (11 and 15), respectively, via olefin cross metathesis reactions. (C) 2004 Published by Elsevier Ltd.
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