化学
差向异构体
立体化学
全合成
戒指(化学)
立体专一性
对映选择合成
分子
碎片(计算)
双键
绝对构型
级联
有机化学
催化作用
操作系统
色谱法
计算机科学
作者
Jun-Jie Yin,Yunpeng Wang,Jing-Bo Xue,Feng Zhou,Xiaonan Shan,Ruizhi Zhu,Kun Fang,Lei Shi,Shu‐Yu Zhang,Si‐Hua Hou,Wujiong Xia,Yong‐Qiang Tu
摘要
The first total syntheses of polycyclic diterpenes phomopsene (1), methyl phomopsenonate (2), and iso-phomopsene (3) have been accomplished through the unusual cascade reorganization of C-C single bonds. This approach features: (i) a synergistic Nazarov cyclization/double ring expansions in one-step, developed by authors, to rapid and stereospecific construction of the 5/5/5/5 tetraquinane scaffold bearing contiguous quaternary centers and (ii) a one-pot strategic ring expansion through Beckmann fragmentation/recombination to efficiently assemble the requisite 5/5/6/5 tetracyclic skeleton of the target molecules 1-3. This work enables us to determine that the correct structure of iso-phomopsene is, in fact, the C7 epimer of the originally assigned structure. Finally, the absolute configurations of three target molecules were confirmed through enantioselective synthesis.
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