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An updated asymmetric total synthesis of (+)-tronocarpine
Tetrahedron ( IF 2.1 ) Pub Date : 2020-10-03 , DOI: 10.1016/j.tet.2020.131641
Dong-Xing Tan , Jie Zhou , Fu-She Han

An updated route for the asymmetric total synthesis of (+)-tronocarpine is presented. By a careful modification of the synthetic strategies and methods for the construction of azepanone ring and for the incorporation of acetyl side group at C20 based on our experiences for the synthesis of chippiine-dippinine type indole alkaloids, the synthesis of (+)-tronocarpine could be shortened from 15 longest linear sequences (LLSs) to 11 LLSs starting from an easily prepared intermediate. The new synthetic route presented herein would provide a more efficient synthesis of (+)-tronocarpine as well as its analogues for biological evaluation which remained unexplored due to the paucity of natural sources.



中文翻译:

一种更新的不对称全合成(+)-香豆素

提供了更新的路线为(+)-tronocarpine不对称全合成。根据我们合成片上碱-二哌啶型吲哚生物碱的经验,合成(+)-香豆蔻碱的经验,通过仔细修改用于构建氮杂环庚酮环和在C 20引入乙酰基侧基的合成策略和方法从容易准备的中间体开始,可以将其从15个最长线性序列(LLS)缩短为11个LLS。本文提出的新的合成途径将提供更有效的(+)-香豆碱及其类似物的合成,以用于生物学评估,由于缺乏天然来源,该合成途径仍未开发。

更新日期:2020-11-12
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