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Asymmetric Total Syntheses of Schizozygane Alkaloids
Journal of the American Chemical Society ( IF 15.0 ) Pub Date : 2021-11-19 , DOI: 10.1021/jacs.1c10279
Wenqiang Zhou 1 , Tao Zhou 1 , Mengxing Tian 1 , Yan Jiang 1 , Jiaojiao Yang 1 , Shuai Lei 1 , Qi Wang 1 , Chongzhou Zhang 1 , Hanyue Qiu 1 , Ling He 1 , Zhen Wang 1 , Jun Deng 1 , Min Zhang 1
Affiliation  

The concise, collective, and asymmetric total syntheses of four schizozygane alkaloids, which feature a “Pan lid”-like hexacyclic core scaffold bearing up to six continuous stereocenters, including two quaternary ones, are described. A new method of dearomative cyclization of cyclopropanol onto the indole ring at C2 was developed to build the ABCF ring system of the schizozygane core with a ketone group. Another key skeleton-building reaction, the Heck/carbonylative lactamization cascade, ensured the rapid assembly of the hexacyclic schizozygane core and concurrent installation of an alkene group. By strategic use of these two reactions and through late-stage diversifications of the functionalized schizozygane core, the first and asymmetric total syntheses of (+)-schizozygine, (+)-3-oxo-14α,15α-epoxyschizozygine, and (+)-α-schizozygol and the total synthesis of (+)-strempeliopine have been accomplished in 11–12 steps from tryptamines.

中文翻译:

裂合生物碱的不对称全合成

描述了四种裂合生物碱的简明、集体和不对称的全合成,其特征在于具有多达六个连续立体中心(包括两个四元立体中心)的“盘盖”状六环核心支架。开发了一种环丙醇在C2处的吲哚环上脱芳环的新方法,以构建具有酮基的裂合核的ABCF环系统。另一个关键的骨架构建反应,即 Heck/羰基化内酰胺化级联反应,确保了六环裂合核的快速组装和烯烃基团的同时安装。通过战略性地利用这两个反应和通过功能化裂合核的后期多样化,(+)-裂合子、(+)-3-oxo-14α,15α-epoxyschizozygine 的第一次和不对称全合成,
更新日期:2021-12-01
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