Synthesis and pharmacology of the isomeric methylheptyl-Δ 8-tetrahydrocannabinols

…, J Liddle, SG Duncan, S Yu, BR Martin, JL Wiley

Index: Huffman, John W.; Liddle, John; Duncan Jr., Sammy G.; Yu, Shu; Martin, Billy R.; Wiley, Jenny L. Bioorganic and Medicinal Chemistry, 1998 , vol. 6, # 12 p. 2383 - 2396

Full Text: HTML

Citation Number: 31

Abstract

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 ...