含有1,4-苯二氧杂环的反式二氢精氨酸衍生物的立体选择性合成。

IF 1.7 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Monatshefte Fur Chemie Pub Date : 2018-01-01 Epub Date: 2018-10-26 DOI:10.1007/s00706-018-2287-7

Gábor Varró, Balázs Pogrányi, Alajos Grün, András Simon, László Hegedűs, István Kádas

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引用次数: 4

摘要

摘要/ Abstract摘要:利用我们最近发展的可行而高效的方法，立体选择性合成了一些新的含1,4-苯二氧杂环的反式二氢精氨酸衍生物。这些新的非硝唑酮生物碱类似物有外消旋和旋光性两种形式。应用(8S,9S)-9-氨基(9-脱氧)epiquinine作为有机催化剂，获得了高的对映选择性(高达99% ee)。由于副反应，还制备了各种甲氧菲那啶区域异构体，从而进一步合成了在菲那啶支架a环上修饰的反式二氢精氨酸类似物。图形化的简介:

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Stereoselective synthesis of trans-dihydronarciclasine derivatives containing a 1,4-benzodioxane moiety.

Abstract: Some new trans-dihydronarciclasine derivatives containing a 1,4-benzodioxane moiety were stereoselectively synthesised using our feasible and efficient method developed recently. These new phenanthridone alkaloid analogues were obtained in both racemic and optically active forms. High enantioselectivities (up to 99% ee) were achieved by applying (8S,9S)-9-amino(9-deoxy)epiquinine as an organocatalyst. Due to a side reaction, various methoxyphenanthridine regioisomers were also prepared which afforded further synthetic trans-dihydronarciclasine analogues modified in the ring A of the phenanthridone scaffold.

Graphical abstract:

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来源期刊

Monatshefte Fur Chemie 化学-化学综合

CiteScore

3.70

自引率

5.60%

发文量

116

审稿时长

3.3 months

期刊介绍： "Monatshefte für Chemie/Chemical Monthly" was originally conceived as an Austrian journal of chemistry. It has evolved into an international journal covering all branches of chemistry. Featuring the most recent advances in research in analytical chemistry, biochemistry, inorganic, medicinal, organic, physical, structural, and theoretical chemistry, Chemical Monthly publishes refereed original papers and a section entitled "Short Communications". Reviews, symposia in print, and issues devoted to special fields will also be considered.