Bioorganic and Medicinal Chemistry p. 2383 - 2396 (1998)
Update date:2022-08-05
Topics:
Huffman, John W.
Liddle, John
Duncan Jr., Sammy G.
Yu, Shu
Martin, Billy R.
Wiley, Jenny L.
The synthesis of the 3-heptyl, and the eleven isomeric 3-methylheptyl-Δ8-tetrahydrocannabinols (3-7, R and S methyl epimers, and 8) has been carried out. The synthetic approach entailed the synthesis of substituted resorcinols, which were subjected to acid catalyzed condensation with trans-para-menthadienol to provide the Δ8-THC analogue. The 1'-, 2'- and 3'-methylheptyl analogues (3-5) are considerably more potent than Δ8-THC. The 4'-, 5'- and 6'-methylheptyl isomers (6-8) are approximately equal in potency to Δ8-THC. Copyright (C) 1998 Elsevier Science Ltd.
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