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Title: | Base-Mediated Nitrophenyl Reductive Cyclization for the Synthesis of Hexahydro-2,6-methano-1-benzazocines |
Author: | Rodríguez, Laura G. Delgado, Ana Ciudad i Gómez, Carlos Julián Noé Mata, Verónica Bonjoch i Sesé, Josep Bradshaw, Ben |
Keywords: | Hidrocarburs Cromatografia Purificació Hydrocarbons Chromatography Purification |
Issue Date: | 3-Nov-2022 |
Publisher: | American Chemical Society |
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 4h, bearing an enone moiety, which was active against eight cancer cell lines. |
Note: | Reproducció del document publicat a: https://doi.org/10.1021/acs.joc.2c02205 |
It is part of: | Journal of Organic Chemistry, 2022, vol. 87, num.22, p. 15693-15702 |
URI: | http://hdl.handle.net/2445/214253 |
Related resource: | https://doi.org/10.1021/acs.joc.2c02205 |
ISSN: | 0022-3263 |
Appears in Collections: | Articles publicats en revistes (Institut de Biomedicina (IBUB)) Articles publicats en revistes (Bioquímica i Fisiologia) |
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