立体选择性地从（−）左旋葡萄糖酮中获得生物活性环丙烷(+)-PPCC和(1R,2S)-2-氨基甲基-1-芳基环丙烷-1-羧酰胺

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters Pub Date : 2025-04-18 DOI:10.1016/j.tetlet.2025.155620

Edward T. Ledingham, Johannes Puschnig, Ben W. Greatrex

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引用次数: 0

摘要

纤维素热解得到的手性合成物(−)-左旋葡萄糖酮（LGO）转化为两种已知的生物活性化合物：5 -羟色胺-去甲肾上腺素-多巴胺再摄取抑制剂(1R,2S)-2-（氨基甲基）- n， n-二乙基-1-（萘-2-基）环丙烷-1-羧酰胺和σ−受体配体(+)- ppcc。该工艺的关键步骤是通过Suzuki-Miyaura交叉偶联反应将LGO衍生物芳基化，然后在Johnson-Corey-Chaykovsky条件下进行环丙烷化。采用Baeyer-Villiger和NaIO4介导氧化进行脱同源化，然后官能团相互转化得到具有生物活性的环丙烷。每个目标的几个衍生物被开发，证明了芳基和胺基取代过程的多功能性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Stereoselective access to bioactive cyclopropanes (+)-PPCC and (1R,2S)-2-aminomethyl-1-arylcyclopropane-1-carboxamides from (−)-levoglucosenone

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Stereoselective access to bioactive cyclopropanes (+)-PPCC and (1R,2S)-2-aminomethyl-1-arylcyclopropane-1-carboxamides from (−)-levoglucosenone

The chiral synthon (−)-levoglucosenone (LGO) obtained from cellulose pyrolysis has been transformed into two known bioactive compounds: the serotonin-norepinephrine-dopamine reuptake inhibitor (1R,2S)-2-(aminomethyl)-N,N-diethyl-1-(naphthalen-2-yl)cyclopropane-1-carboxamide and the σ₋receptor ligand (+)-PPCC. The key steps in the process were the arylation of an LGO derivative via a Suzuki-Miyaura cross-coupling reaction, then cyclopropanation under Johnson-Corey-Chaykovsky conditions. Dehomologation was achieved using Baeyer-Villiger and NaIO₄ mediated oxidation, and then functional group interconversion gave the bioactive cyclopropanes. Several derivatives of each target were developed demonstrating the versatility of the process for aryl and amine group substitution.

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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.