biostudies-literatureRodriguez LGMinisterio de Ciencia e Innovación15693-15702https://www.ebi.ac.uk/biostudies/studies/S-EPMC9680033biostudies-literatureUnknown87(22)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 <b>4h</b>, bearing an enone moiety, which was active against eight cancer cell lines.The Journal of organic chemistryBase-Mediated Nitrophenyl Reductive Cyclization for the Synthesis of Hexahydro-2,6-methano-1-benzazocines.PMC9680033PID2019-104188GB-I00RTI2018-093901-B-I00Noe VBonjoch JCiudad CJBradshaw BRodriguez LGDelgado AfalseBase-Mediated Nitrophenyl Reductive Cyclization for the Synthesis of Hexahydro-2,6-methano-1-benzazocines.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 <b>4h</b>, bearing an enone moiety, which was active against eight cancer cell lines.2022-01-01T00:00:00Z2022 Nov2025-04-05T10:57:36.186Z2025-04-05T10:57:36.186ZS-EPMC96800333632956010.1021/acs.joc.2c02205