Synthetic studies towards arcutinidine: An alternative strategy for construction of the complete carbon framework. (23rd April 2021)

• Record Type: Journal Article
• Authors: Wu, Xiaoqing; Nie, Wei; Fu, Min; Liu, Xiao-Yu; Xue, Fei; Qin, Yong
• Is Part Of: Tetrahedron. Volume 86:(2021)
• Publication Date: 2021-04-23
• Subjects: C20-diterpenoid alkaloids -- Arcutinidine -- Total synthesis -- Oxidative dearomatization/IMDA cascade -- Ketyl-olefin cyclization; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2021.132092
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A synthetic approach to the complete carbon framework of C20 -diterpenoid alkaloid arcutinidine has been achieved. The key steps include a 1, 4-conjugate addition and a palladium-catalyzed decarboxylative allylation to install the two vicinal all-carbon quaternary centers at C4 and C5; an oxidative dearomatization/IMDA cascade reaction to forge the C/D/F ring, and a ketyl-olefin cyclization to construct the B ring. Graphical abstract: Image 1 Highlights: Alternative approach to the complete carbon framework of C20 -diterpenoid alkaloid arcutinidine. Synthetic strategy based on the bioinspired late-stage formation of the pyrrolidine ring through C-H amination. A 1, 4-conjugate addition and a palladium-catalyzed decarboxylative allylation to forge the two vicinal C4, C5 all-carbon quaternary centers. atization/IMDA cascade reaction to forge the C/D/F ring in one-pot. SmI2 -mediated ketyl-olefin cyclization to construct the B ring.