Novel total syntheses of oxoaporphine alkaloids enabled by mild Cu-catalyzed tandem oxidation/aromatization of 1-Bn-DHIQs

Bo Zheng; Hui-Ya Qu; Tian-Zhuo Meng; Xia Lu; Jie Zheng; Yun-Gang He; Qi-Qi Fan; Xiao-Xin Shi

doi:10.1039/c8ra05338c

Novel total syntheses of oxoaporphine alkaloids enabled by mild Cu-catalyzed tandem oxidation/aromatization of 1-Bn-DHIQs

RSC Adv. 2018 Aug 14;8(51):28997-29007. doi: 10.1039/c8ra05338c.

Authors

Bo Zheng¹, Hui-Ya Qu¹, Tian-Zhuo Meng¹, Xia Lu¹, Jie Zheng¹, Yun-Gang He¹, Qi-Qi Fan¹, Xiao-Xin Shi¹

Affiliation

¹ Shanghai Key Laboratory of Chemical Biology and Department of Pharmaceutical Engineering, School of Pharmacy, East China University of Science and Technology 130 Mei-Long Road Shanghai 200237 P. R. China xxshi@ecust.edu.cn.

Abstract

Novel total syntheses of oxoaporphine alkaloids such as liriodenine, dicentrinone, cassameridine, lysicamine, oxoglaucine and O-methylmoschatoline were developed. The key step of these total syntheses is Cu-catalyzed conversion of 1-benzyl-3,4-dihydro-isoquinolines (1-Bn-DHIQs) to 1-benzoyl-isoquinolines (1-Bz-IQs) via tandem oxidation/aromatization. This novel Cu-catalyzed conversion has been studied in detail, and was successfully used for constructing the 1-Bz-IQ core.