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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.
|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.||摘要:||
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.
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