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Paper | Special issue | Vol 99, No. 1, 2019, pp.310-323
Published online, 3rd September, 2018
DOI: 10.3987/COM-18-S(F)26
Synthetic Studies on Plakinidines

Takahito Satoh, Touma Adachi, Kentaro Okano, Juri Sakata, and Hidetoshi Tokuyama*

*Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aoba, Aramaki, Aoba-ku, Sendai, 980-8578, Japan

Abstract

Synthetic studies on plakinidines are described. As a model study for the construction of the dihydropyridone ring at the final stage of the synthesis, we investigated a Meyer–Schuster rearrangement/aza-Michael cyclization cascade. The B,C,D,E ring system possessing a pyrrolo[2,3,4-kl]acridine structure was constructed via a benzyne-mediated cyclization/functionalization sequence that involved the formation of a β,β-diarylethylamine derivative and a palladium-catalyzed double aryl amination of a 3-arylindoline intermediate as key processes.