Graduate School of Pharmaceutical Sciences, University of Tokyo, Tokyo, Japan.
Angew Chem Int Ed Engl. 2012 Sep 3;51(36):9160-3. doi: 10.1002/anie.201204726. Epub 2012 Aug 2.
What a core-ker! The title synthesis was achieved using a route featuring an intramolecular Mitsunobu reaction of a nosyl amide, stereoselective construction of the β-lactam, and formation of an enamide moiety by selenoxide elimination. The stereochemistry of the alkylation for the formation of the β-lactam was controlled by a secondary hydroxy group on the ten-membered ring. SEM=2-(trimethylsilyl)ethoxymethyl; TBS=tert-butyldimethylsilyl.
真是太棒了！标题的合成都采用了一种方法，该方法涉及亚硝酰酰胺的分子内 Mitsunobu 反应、β-内酰胺的立体选择性构建以及硒氧化物消除形成烯酰胺部分。β-内酰胺形成的烷基化的立体化学由十元环上的仲羟基控制。SEM=2-(三甲基甲硅烷基)乙氧基甲基；TBS=叔丁基二甲基硅基。
