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Studies on cannabinoids part vi synthesis and biological evaluation of trans 4a 10a 3 methyl 5 hydroxy 7 n pentyl 1 2 3 4 4a 9 10 10a octahydrophenanthrene



Studies on cannabinoids part vi synthesis and biological evaluation of trans 4a 10a 3 methyl 5 hydroxy 7 n pentyl 1 2 3 4 4a 9 10 10a octahydrophenanthrene



Indian Journal of Chemistry Section B Organic Chemistry Including Medicinal Chemistry 30(2): 195-200



The synthesis of a carbocyclic analog of .DELTA.9-tetrahydrocannabinol is described. Diels-Alder reaction of appropriately substituted cinnamic acid with 2-methylbutadiene gives an adduct with proper substituents and required stereochemistry which is then elaborated to the required molecules 23. When tested in mice it is found to possess mild analgesic activity. Thus replacement of pyran oxygen of tetrahydrocannabinol with a methylene group considerably reduces its analgesic activity.

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