Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 15, Pages 7839-7849Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00988
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Funding
- National Institutes of Health [DA009158, DA023142, DA007215, DA026795]
- Grants-in-Aid for Scientific Research [16K18850] Funding Source: KAKEN
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We report the design, synthesis, and biological evaluation of a novel class of cannabinergic ligands, namely C1 '-azacycloalkyl hexahydrocannabinols. Our synthetic approaches utilize an advanced common chiral intermediate triflate from which all analogues could be derived. Key synthetic steps involve microwave-assisted Liebeskind Srogl C-C cross-coupling and palladium-catalyzed decarboxylative coupling reactions. The C1'-N-methylazetidinyl and C1'-N-methylpyrrolidinyl analogues were found to be high affinity ligands for the CB1 and CB2 cannabinoid receptors..
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