弗勒根灵A和C的全合成
Total Syntheses of Phleghenrines A and C.
作者信息
Cai Xinpei, Li Lei, Wang Ye-Cheng, Zhou Jianhan, Dai Mingji
机构信息
Department of Chemistry and Center for Cancer Research, Purdue University, West Lafayette, Indiana 47907, United States.
Department of Chemistry, Emory University, Atlanta, Georgia 30322, United States.
出版信息
Org Lett. 2023 Jul 21;25(28):5258-5261. doi: 10.1021/acs.orglett.3c01784. Epub 2023 Jul 11.
Herein, we report the total syntheses of phleghenrines A and C from commercially available starting materials in 7 and 8 steps, respectively. Notable steps include an inverse electron-demand Diels-Alder reaction between a masked -benzoquinone and a -protected enamine to prepare one key intermediate with a bicyclo[2.2.2]octenone core, a Büchner-Curtius-Schlotterbeck one-carbon insertion to expand the bicyclo[2.2.2]octenone to a bicyclo[3.2.2]nonenone, and Trauner's modified 2-pyridone synthesis to install the 2-pyridone moiety.
在此，我们报道了分别以市售起始原料经7步和8步全合成法制备出了弗勒根灵A和C。值得注意的步骤包括在一个掩蔽的对苯醌与一个受保护的烯胺之间进行的逆电子需求的狄尔斯-阿尔德反应，以制备具有双环[2.2.2]辛烯酮核心的一个关键中间体；一个布赫纳-库尔提斯-施洛特贝克单碳插入反应，将双环[2.2.2]辛烯酮扩展为双环[3.2.2]壬烯酮；以及特劳纳改进的2-吡啶酮合成法，用于安装2-吡啶酮部分。
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