Universität Potsdam, Institut für Chemie, Karl-Liebknecht-Straße 24-25, D-14476 Potsdam-Golm, Germany.
J Org Chem. 2022 May 6;87(9):5904-5915. doi: 10.1021/acs.joc.2c00195. Epub 2022 Apr 7.
An efficient method for the preparation of arylnaphthalene lignans (ANLs) was developed, which is based on the Photo-Dehydro-Diels-Alder (PDDA) reaction. While intermolecular PDDA reactions turned out to be inefficient, the intramolecular variant using suberic acid as tether linking two aryl propiolic esters smoothly provided naphthalenophanes. The irradiations were performed with a previously developed annular continuous-flow reactor and UVB lamps. In this way, the natural products Alashinol D, Taiwanin C, and an unnamed ANL could be prepared.
开发了一种基于光脱氢 Diels-Alder（PDDA）反应的有效制备芳基萘烷木脂素（ANLs）的方法。虽然分子间 PDDA 反应效率不高，但使用琥珀酸作为连接两个芳基丙炔酸酯的连接物的分子内变体则顺利提供了萘烷环烷。辐照使用之前开发的环形连续流反应器和 UVB 灯进行。通过这种方式，可以制备天然产物 Alashinol D、Taiwanin C 和一种未命名的 ANL。
