Tetrahedron p. 1557 - 1576 (1997)
Update date:2022-08-03
Topics:
Huffman, John W.
Lainton, Julia A.H.
Banner, W. Kenneth
Duncan Jr., Sammy G.
Jordan, Robert D.
Yu, Shu
Dai, Dong
Martin, Billy R.
Wiley, Jenny L.
Compton, David R.
The synthesis of both side chain epimers of 1'- (4), 2'- (5), 3'-methyl- (6) and 4'-methyl-Δ8-tetrahydrocannobinol (7) has been carried out. The synthetic approach entailed the acid catalyzed condensation of the appropriate substituted resorcinol with menthadienol to provide the Δ8-THC analogue. Both isomers of 1'- (4) and 2'-Δ8-THC (5) were more potent than Δ8-THC, both in vitro and in vivo. The 3'-methyl isomers (6) were approximately equal in potency to Δ8-THC, and 4'-methyl-Δ8-THC was less potent. There was relatively little difference in potency between the epimers of 4, 5, and 6.
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