Abstract
A synthetic approach to the complete carbon framework of C 20 -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. • Alternative approach to the complete carbon framework of C 20 -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. • SmI 2 -mediated ketyl-olefin cyclization to construct the B ring.
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