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標題: A C2-Symmetric Pool Based Flexible Strategy: An Enantioconvergent Synthesis of (+)-Valiolamine and (+)-Valienamine
作者: Lo, H.J.
Chen, C.Y.
Zheng, W.L.
Yeh, S.M.
Yan, T.H.
關鍵字: Amino pseudosugars;Chiral pool;Natural products;Cyclization;Inhibitors;ring-closing metathesis;enantiospecific syntheses;efficient synthesis;validoxylamine-g;(-)-quinic acid;valienamine;valiolamine;inhibitors;diastereomers;validamycin
Project: European Journal of Organic Chemistry
期刊/報告no:: European Journal of Organic Chemistry, Issue 14, Page(s) 2780-2785.
A new enantioconvergent strategy directed toward the synthesis of glucosidase inhibitors was developed by using a C2-symmetric element within the chiral pool and by applying an iodine-promoted cyclization of an unsaturated carbonimidothioate for the regio- and diastereocontrolled installation of amino and hydroxy units. Not only does this simple flexible strategy provide a convergent concise approach to (+)-valiolamine (1), but it can also be readily adopted for the synthesis of (+)-valienamine (2). Commercially available and cheap C2-symmetric D-tartaric acid served as the chiral building block.
ISSN: 1434-193X
DOI: 10.1002/ejoc.201101845
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