{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Rodriguez LG"],"funding":["Ministerio de Ciencia e Innovación"],"pagination":["15693-15702"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC9680033"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["87(22)"],"pubmed_abstract":["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."],"journal":["The Journal of organic chemistry"],"pubmed_title":["Base-Mediated Nitrophenyl Reductive Cyclization for the Synthesis of Hexahydro-2,6-methano-1-benzazocines."],"pmcid":["PMC9680033"],"funding_grant_id":["PID2019-104188GB-I00","RTI2018-093901-B-I00"],"pubmed_authors":["Noe V","Bonjoch J","Ciudad CJ","Bradshaw B","Rodriguez LG","Delgado A"],"additional_accession":[]},"is_claimable":false,"name":"Base-Mediated Nitrophenyl Reductive Cyclization for the Synthesis of Hexahydro-2,6-methano-1-benzazocines.","description":"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.","dates":{"release":"2022-01-01T00:00:00Z","publication":"2022 Nov","modification":"2025-04-05T10:57:36.186Z","creation":"2025-04-05T10:57:36.186Z"},"accession":"S-EPMC9680033","cross_references":{"pubmed":["36329560"],"doi":["10.1021/acs.joc.2c02205"]}}