Diastereoselective synthesis of novel alkaloid-like 1,2,3,3a,7b,12-hexahydroindeno[2′,1′:2,3]indeno[1,2-c]pyrroles

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters Pub Date : 2024-11-02 DOI:10.1016/j.tetlet.2024.155358

Vladimir D. Fedorenko, Evgeny M. Buev, Vladimir S. Moshkin, Vyacheslav Y. Sosnovskikh

引用次数: 0

Abstract

2-Arylideneindan-1,3-diones readily undergo [3+2]-cycloaddition with N-methylazomethine ylide derived from sarcosine and formaldehyde to give 4′-aryl-1′-methylspiro[indene-2,3′-pyrrolidine]-1,3-diones, which were further cyclized in perchloric acid to (3aR*,7bR*,12aR*)-7b-hydroxy-2-methyl-2,3,3a,7b-tetrahydroindeno[2′,1′:2,3]indeno[1,2-c]pyrrol-12(1H)-ones in 33–100 % yields.

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新型生物碱样 1,2,3,3a,7b,12-六氢茚并[2′,1′:2,3]茚并[1,2-c]吡咯的非对映选择性合成

2-Arylideneindan-1,3-diones 很容易与从肌氨酸和甲醛中提取的 N-甲基氮杂环丁烷发生 [3+2]-cycloaddition 反应，生成 4′-芳基-1′-甲基螺[茚-2、3′-吡咯烷]-1,3-二酮，在高氯酸中进一步环化为(3aR*,7bR*,12aR*)-7b-羟基-2-甲基-2,3,3a,7b-四氢茚并[2′,1′：2,3]茚并[1,2-c]吡咯-12(1H)-酮，收率为 33-100%。

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来源期刊

Tetrahedron Letters 化学-有机化学

CiteScore

3.50

自引率

5.60%

发文量

521

审稿时长

28 days

期刊介绍： Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.