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Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/214253
Base-Mediated Nitrophenyl Reductive Cyclization for the Synthesis of Hexahydro-2,6-methano-1-benzazocines
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A Diels-Alder reaction leading to 4-nitrophenylcyclohexanones followed by a newly developed base-mediated reductive cyclization of the resulting ketone tethered to the nitrobenzene moiety gives access to the hexahydro-2,6-methano-1-benzazocine ring system present in several biologically interesting natural products such as aspernomine. The scope of the reaction was explored with eight substituted nitrobenzenes, obtaining yields of up to 87%. The highest cytotoxicity was observed in benzazocine 4h, bearing an enone moiety, which was active against eight cancer cell lines.
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RODRÍGUEZ, Laura G., et al. Base-Mediated Nitrophenyl Reductive Cyclization for the Synthesis of Hexahydro-2,6-methano-1-benzazocines. Journal of Organic Chemistry. 2022. Vol. 87, num. 22, pags. 15693-15702. ISSN 0022-3263. [consulted: 10 of June of 2026]. Available at: https://hdl.handle.net/2445/214253