立体选择性地加成烯丙基金属试剂到游离的和保护的 syn-α,β-二羟基酮，为甲基金三氧化杀癌醇 A 的有效合成途径提供了可能。
Diastereoselective additions of allylmetal reagents to free and protected syn-α,β-dihydroxyketones enable efficient synthetic routes to methyl trioxacarcinoside A.
机构信息
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
出版信息
Org Lett. 2012 Apr 6;14(7):1812-5. doi: 10.1021/ol300377a. Epub 2012 Mar 9.
Abstract
Two routes to the 2,6-dideoxysugar methyl trioxacarcinoside A are described. Each was enabled by an apparent α-chelation-controlled addition of an allylmetal reagent to a ketone substrate containing a free α-hydroxyl group and a β-hydroxyl substituent, either free or protected as the corresponding di-tert-butylmethyl silyl ether. Both routes provide practical access to gram quantities of trioxacarcinose A in a form suitable for glycosidic coupling reactions.
摘要
描述了通向 2,6-二去氧糖基三甲氧基碳环霉素 A 的两条路线。每条路线都是通过烯丙基金属试剂对含有游离α-羟基和β-羟基取代基的酮底物的明显α-螯合控制加成来实现的，所述取代基可以是游离的，也可以是作为相应的二叔丁基甲基硅醚保护的。两条路线都提供了实用的方法来获得克级数量的适合糖苷偶联反应的三氧碳环霉素 A 形式。
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