Reductive SN2’ Reaction of Epoxydienoate with Borane and its Application to the Synthesis and Structural Revision of an Antitumor Active Torrubiellutin Analogue
Reductive SN2’ Reaction of Epoxydienoate with Borane and its Application to the Synthesis and Structural Revision of an Antitumor Active Torrubiellutin Analogue
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环氧二烯酸酯与硼烷的还原SN2’反应及其在抗肿瘤活性托鲁比鲁丁类似物的合成和结构修饰中的应用
DOI：
10.1002/asia.202200650
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发表时间：
2022
期刊：
影响因子：
--
通讯作者：
Nagumo Shinji
中科院分区：
文献类型：
--
作者：
Murokawa Shunsuke;Furukawa Koki;Kawano Yoshinori;Nihei Tsukasa;Suzuki Yuji;Yasui Eiko;Nagumo Shinji
开发了环氧二烯酸酯和环氧烯酸酯与硼烷的还原SN2’反应，以提供跳跃的二烯酸酯和非共轭烯酸酯，其中三取代的Z-烯烃在一侧或两侧连接到不对称中心。该反应成功应用于替代合成具有抗肿瘤活性的torrubiellutin C人工类似物，并合成了该人工类似物的α,β-不饱和酰胺的几何异构体。这些合成阐明了具有抗肿瘤活性的 Torrubiellutin C 人工类似物的真实结构。
A reductive SN2’ reaction of epoxydienoates and epoxyenoates with borane was developed to afford skipped dienoates and unconjugated enoates with trisubstitutedZ‐alkene linked to asymmetric centers on one side or both sides. This reaction was successfully applied to the alternative synthesis of an antitumor active artificial analogue of torrubiellutin C. A geometric isomer for α,β‐unsaturated amide of the artificial analogue was also synthesized. These syntheses clarified the true structure of the antitumor active artificial analogue of torrubiellutin C.