Short‐Cut Bio‐Inspired Synthesis of Tricyclic Guanidinic Motifs of Crambescidins and Batzelladines Marine Alkaloids,European Journal of Organic Chemistry

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Short‐Cut Bio‐Inspired Synthesis of Tricyclic Guanidinic Motifs of Crambescidins and Batzelladines Marine Alkaloids
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2020-06-25 , DOI: 10.1002/ejoc.202000744
Amr El-Demerdash ₁ , Ludmila Ermolenko ₂ , Emmanuelle Gros ₃ , Pascal Retailleau ₄ , Binh Nguyen Thanh ₅ , Gauvin-Bialecki Anne ₆ , Ali Al-Mourabit ₇

Affiliation

A convenient short synthesis of tricyclic guanidine‐containing natural products featuring four‐component reaction between 2,5‐dimethoxytetrahydrofuran, 2‐aminopyrimidine and two acylacetic or benzoylacetic acids is reported. A synthetic route combining the Robinson–Schöepf bioinspired strategy and biomechanistic analysis of the crambescidin and batzelladine alkaloids family is developed. An application of this strategy to the synthesis of two unnatural diastereoisomers of merobatzelladine B is described.

中文翻译：

短促生物启发的Crambescidins和Batzelladines海洋生物碱三环鸟苷酸基序的合成

据报道，一种方便的短合成三环含胍的天然产物具有2，5-二甲氧基四氢呋喃，2-氨基嘧啶与两种酰基乙酸或苯甲酰乙酸之间的四组分反应。开发了一条综合途径，结合了罗宾逊-舍弗夫的生物启发策略和克拉贝西丁和巴兹拉丁生物碱家族的生物力学分析。描述了该策略在合成甲巴非特拉丁B的两种非天然非对映异构体中的应用。

更新日期：2020-06-25

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