Stereoselective Synthesis of the Epimeric Δ7-Tetrahydrocannabinols

Authors

John W. Huffman, Clemson University
W. Kenneth Banner, Clemson University
Grace K. Zaroob, Clemson University
H. Howard Joyner, Clemson University
Patricia H. Reggio, Kennesaw State UniversityFollow
Billy R. Martin, Medical College of VirginiaFollow
David R. Compton, Medical College of VirginiaFollow

Document Type

Article

Publication Date

1-1995

Abstract

Both C9 epimers of Δ⁷-THC (3 and 4) have been synthesized from Δ⁸-THC methyl ether (12). Hydroboration of 12 gave a mixture of stereoisomeric 8-hydroxyhexahydrocannabinols. The 8α-ol was converted into the 9β-methyl epimer (4) of Δ⁷-THC, while the 8β-ol was converted into 3. Molecular modeling indicated that 4 should have significant cannabinoid activity, while 3 was predicted to be weakly active. These predictions were borne out by both in vitro and in vivo pharmacology.