Synthesis of both enantiomers of nabilone from a common intermediate. Enantiodivergent synthesis of cannabinoids

…, MD Lee, RD Jordan, WT Pennington

Index: Huffman; Joyner; Lee; Jordan; Pennington Journal of Organic Chemistry, 1991 , vol. 56, # 6 p. 2081 - 2086

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Citation Number: 25

Abstract

Both enantiomers of the synthetic cannabinoid nabilone (4) have been synthesized from a common intermediate, enone 7. Enone 7 was prepared by reaction of [2, 6-dimethoxy-4-(l, l- dimethylheptyl) phenyl] lithium with (+)-apoverbenone (2), followed by PDC oxidation. Li/NH3 reduction of 7 gave saturated ketone 9, which, after ether cleavage to 10, afforded (6aS, lOaR)-hexahydrodibenzopyran 15 on reaction with SnC14 Isomerization to 6aR, ...

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