非对称3,3'-双香豆素的合成：蒿甲醚C、3,3'-双异嗪皮啶和双羟香豆素的全合成

Synthesis of Nonsymmetrical 3,3'-Bicoumarins: Total Synthesis of Arteminorin C, 3,3'-Biisofraxidin, and Biscopoletin.

作者信息

Castañón-García Mario, López-Mendoza Pedro, Galicia-Badillo Dazaet, Miranda Luis D

机构信息

Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior S.N., Ciudad Universitaria, Coyoacán, Ciudad de México 04510, Mexico.

Postdoctoral Associate CONAHCyT, Centro de Investigación de la Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla (BUAP), 14 Sur Esq. San Claudio, Col. San Manuel, 72570 Puebla, Mexico.

出版信息

Org Lett. 2025 May 30;27(21):5349-5354. doi: 10.1021/acs.orglett.5c01119. Epub 2025 May 20.

DOI:10.1021/acs.orglett.5c01119

PMID:40393027

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12131221/

Abstract

A strategy to access nonsymmetrical 3,3'-bicoumarins employing two consecutive Perkin reactions is reported. This approach is based on the initial formation of coumarin acetic acid from a salicylaldehyde derivative through a Perkin reaction. A second Perkin condensation between the previously formed coumarin acetic acid and a new functionalized salicylaldehyde allows the formation of nonsymmetrical 3,3'-bicoumarins. Using this approach, 17 nonsymmetrical and two symmetrical 3,3'-bicoumarins were prepared in yields ranging from 30% to 86%, and natural products arteminorin C, 3,3'-biisofraxidin, and biscopoletin were obtained.

摘要

报道了一种采用两个连续的珀金反应来合成非对称3,3'-联香豆素的策略。该方法基于通过珀金反应从水杨醛衍生物初步形成香豆素乙酸。先前形成的香豆素乙酸与新的功能化水杨醛之间的第二次珀金缩合反应可形成非对称3,3'-联香豆素。采用这种方法，制备了17种非对称和2种对称的3,3'-联香豆素，产率在30%至86%之间，并且获得了天然产物阿尔特米诺林C、3,3'-二异秦皮啶和双羟香豆素。