Aconitine synthesis studies. A modeling construction of the functionalized BCDE tetracyclic ring system. Issue 3 (19th December 2022)

• Record Type: Journal Article
• Authors: Guo, Tianyuan; Peng, Fuli; Song, Xueqin; Lei, Jiang; Yu, Fangzhou; Chu, Hongping; Yang, Keyang; Xu, Liang
• Is Part Of: Organic chemistry frontiers. Volume 10:Issue 3(2023)
• Page Start: 675
• Page End: 679
• Publication Date: 2022-12-19
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d2qo01740g
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A highly functionalized BCDE model ring system of aconitine has been synthesized for the first time via a strategy involving oxidative dearomatization/IMDA, Wagner–Meerwein rearrangement, Michael addition and reductive cyclization. Abstract : The first model synthesis of the fully functionalized BCDE tetracyclic analogue 2 of aconitine has been accomplished. A tricyclic intermediate was prepared through highly stereospecific reduction of the ketone intermediates 14 and 16 as well as the following facile Wagner–Meerwein rearrangement. A stereoselective Michael addition and reductive cyclization involving a sequential nitrile hydration and silane promoted reduction were exploited to construct the nitrogen containing six-membered E ring bearing vicinal tertiary and quaternary centers.