The synthesis of some 11-substituted tetrahydrocannabinol metabolites

John W. ApSimon, T. Lee Collier, Michael D. Guiver
1982 Canadian journal of chemistry (Print)  
npsi/ctrl?action=rtdoc&an=8934250〈=en http://nparc.cisti-icist.nrc-cnrc.gc.ca/npsi/ctrl?action=rtdoc&an=8934250〈=fr Access and use of this website and the material on it are subject to the Terms and Conditions set forth at . Can. J. Chem. 60,2804Chem. 60, (1982. 9-Bromo-l l-oxo-hexahydrocannabinol (5) was prepared from the ketocannabinoid 36 via the epoxysulfone 4. Thedehydrobromination of the bromoaldehyde 5 could be controlled to give either the thermodynamically more stable A8-aldehyde 2c,
more » ... e A8-aldehyde 2c, or the A9-aldehyde lc by an intramolecularly assisted elimination. Reduction of the unsaturated aldehydes gave the allylic alcohol metabolites 2a and la, respectively. JOHN W. APSIMON, T. LEE COLLIER et MICHAEL D. GUIVER. Can. J. Chem. 60,2804 (1982 . On a separe le bromo-9 0x0-11 hexahydrocannabinol(5) i partir du ~Ctocannabinoi'de 3b via 1'6poxysulfone 4. On peut controler la dehydrobromation du bromaldehyde 5 pour obtenir soit le As-aldehyde (2c) thermodynamiquement le plus stable, soit le A9-aldthyde (lc) par une elimination intramolCculaire assistee. La reduction des aldehydes insatures a conduit a I'alcool allylique des mttabolites 2n et la respectivement. [Traduit par le journal]
doi:10.1139/v82-403 fatcat:neakuxz4f5hsrhssgqwrsgikrq