全合成
仿生合成
艾伦
化学
酮
串联
戒指(化学)
衍生工具(金融)
立体化学
生物碱
有机化学
催化作用
金融经济学
复合材料
经济
材料科学
作者
Yang Zhao,Qiuyuan Tan,Yan Jiang,Jiaojiao Yang,Xiaojiao Su,Zhen Qiao,Wenqiang Zhou,Ling He,Han‐Yue Qiu,Min Zhang
标识
DOI:10.1002/ange.202102416
摘要
Abstract We report here a concise, collective, and asymmetric total synthesis of sarpagine alkaloids and biogenetically related koumine alkaloids, which structurally feature a rigid cage scaffold, with L ‐tryptophan as the starting material. Two key bridged skeleton‐forming reactions, namely tandem sequential oxidative cyclopropanol ring‐opening cyclization and ketone α‐allenylation, ensure concurrent assembly of the caged sarpagine scaffold and installation of requisite derivative handles. With a common caged intermediate as the branch point, by taking advantage of ketone and allene groups therein, total synthesis of five sarpagine alkaloids (affinisine, normacusine B, trinervine, N a ‐methyl‐16‐epipericyclivine, and vellosimine) with various substituents and three koumine alkaloids (koumine, koumimine, and N ‐demethylkoumine) with more complex cage scaffolds has been accomplished.
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