文献类型：期刊文献

中文题名：基于光氧化反应的1-苯甲酰基-3,4-二氢异喹啉类生物碱Nelumstemine和Longifolonine的首次全合成

英文题名：First Total Syntheses of 1-Benzoyl-3,4-dihydroisoquinoline Alkaloids Nelumstemine and Longifolonine Based on the Photo-oxidation

作者：黄永康[1];解文静[1];罗永强[1];范琪琦[1];朱星亮[1];刘世领[2];施小新[1]

机构：[1]华东理工大学药学院制药工程与过程化学教育部工程研究中心,上海200237;[2]青平药业有限公司,上海201710

年份：2020

卷号：40

期号：5

起止页码：1281

中文期刊名：有机化学

外文期刊名：Chinese Journal of Organic Chemistry

收录：CSTPCD;;Scopus;WOS:【SCI-EXPANDED(收录号:WOS:000550196500017)】；北大核心:【北大核心2017】；CSCD:【CSCD2019_2020】；

基金：Project supported by the National Natural Science Foundation of China (Nos. 20972048, 20172015).

语种：中文

中文关键词：苯甲酰基二氢异喹啉生物碱;光氧化;Nelumstemine;Longifolonine

外文关键词：benzoyl dihydroisoquinoline alkaloids;photo-oxygenation;nelumstemine;longifolonine

摘要：研究了1-苯甲酰基-3,4-二氢异喹啉生物碱的一条新的合成路线.以3,4-二甲氧基苯甲醛为起始原料,通过6步反应,以50%的总收率首次全合成得到生物碱Nelumstemine;另外,以香兰醛为起始原料,通过9步反应,以35%的总收率首次全合成得到生物碱Longifolonine.上述全合成的关键步骤为,可见光照射下1-苄基-3,4-二氢异喹啉在室温下被空气氧化为1-苯甲酰基-3,4-二氢异喹啉的反应,并对此温和的光化学反应进行了详细研究.
A novel synthetic route for the total syntheses of 1-benzoyl-3,4-dihydroisoquinoline alkaloids was developed.Nelumstemine was synthesized for the first time via 6 steps in 50%overall yield starting from 3,4-dimethoxybenzaldehyde,and longifolonine was also synthesized for the first time via 9 steps in 35%overall yield starting from vanillin.The key step of these total syntheses is photo-oxidation of 1-benzyl-3,4-dihydroisoquinolines to 1-benzoyl-3,4-dihydroisoquinolines by air under visible-light irradiation at room temperature.The unique mild photo-oxidation of 1-benzyl-3,4-dihydro-isoquinolines has been studied in detail.