化学
全合成
立体中心
立体化学
戒指(化学)
酮
烯烃
对映选择合成
吲哚试验
组合化学
有机化学
催化作用
作者
Wenqiang Zhou,Tao Zhou,Meng-Xing Tian,Yan Jiang,Jiaojiao Yang,Shuai Lei,Qi Wang,Chongzhou Zhang,Han‐Yue Qiu,Ling He,Zhen Wang,Jun Deng,Min Zhang
摘要
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.
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