3 years ago

Synthesis of Polycyclic δ-Lactams with Bridged Benzomorphan Skeleton: Selectivity and Diversity Driven by Substituents

Synthesis of Polycyclic
δ-Lactams with
Bridged Benzomorphan Skeleton: Selectivity and Diversity Driven by
Substituents
Jacek G. Sośnicki, Aleksandra Borzyszkowska, Łukasz Struk, Tomasz J. Idzik, Gabriela Maciejewska
An efficient synthesis of bromofunctionalized 2,6-methano- and 1,5-methano-benzomorphanones, starting from easily available 6-benzyl-3,6-dihydropyridin-2(1H)-ones, is described. Furthermore, the synthesis of bridged benzomorphanones with hitherto not known polycyclic systems containing 2- or 3-azabicyclo[4.1.0]heptane units is developed upon treatment of both 2,6- and 1,5-methanobromobenzomorphans with t-BuOK. The effects of substituents on the diversity and stereoselectivity of both transformations are studied.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b02509

DOI: 10.1021/acs.joc.7b02509

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