Synthetic Studies Towards Arcutinidine: An Alternative Strategy For Construction Of The Complete Carbon Framework

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. (C) 2021 Elsevier Ltd. All rights reserved.