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A one-step method for the .alpha.-arylation of camphor. Synthesis of (-)-cannabidiol and (-)-cannabidiol dimethyl ether
Vaillancourt,Valerie;Albizati,Kim
J. Org. Chem.
1992, Vol.57(13), pp.3627–3631
DOI: 10.1021/jo00039a022
Abstract
The syntheses of (-)-cannabidiol and (-)-cannibidiol dimethyl ether were accomplished via fragmentation of an appropriately substituted 9-bromocamphor derivative. A new method of a-arylation of 3,9-dibromocamphor was shown to provide a variety of a-arylated camphor derivatives in good yield.
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Benzoxocin and benzoxonin derivatives. Novel groups of terpenophenols with central nervous system activity
Houry,Schlomo;Mechoulam,Rapael
J. Med. Chem.
1974, Vol.17(3), pp.287–293
DOI: 10.1021/jm00249a006
Abstract
Condensation of carvone with olivetol gave a mixture of the two C-5 isomers of 5,6-dihydro-7-hydroxy-2-isopropyl-5-methyl-9-pentyl-2,6-methano-2H-1-benzoxin-4-(3H)-one (2a and 3a) and their positional isomer 4. These ketones were reduced to their respective alcohols, 5a, 6a, and 7a, which were converted to the olefins 8a, 9a, 12 and 13. Compounds 2a and 3a were deoxygenated to 10 and 11a. The benzoxonin 15a was obtained from the condensation of olivetol with a-pinene. The 1,2-dimethylheptyl homologs (on C-9) of 2a, 3a, 5a, 6a, 8a, 9a, 11a, and 15a were also prepared. Several of these compounds produced CNS depression in rats at doses equal to or less than those required for the natural ?6- and ?1-tetrahydrocannibinols.
A one-step method for the .alpha.-arylation of camphor. Synthesis of (-)-cannabidiol and (-)-cannabidiol dimethyl ether
Vaillancourt,Valerie;Albizati,Kim
J. Org. Chem.
1992, Vol.57(13), pp.3627–3631
DOI: 10.1021/jo00039a022
Abstract
The syntheses of (-)-cannabidiol and (-)-cannibidiol dimethyl ether were accomplished via fragmentation of an appropriately substituted 9-bromocamphor derivative. A new method of a-arylation of 3,9-dibromocamphor was shown to provide a variety of a-arylated camphor derivatives in good yield.
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Benzoxocin and benzoxonin derivatives. Novel groups of terpenophenols with central nervous system activity
Houry,Schlomo;Mechoulam,Rapael
J. Med. Chem.
1974, Vol.17(3), pp.287–293
DOI: 10.1021/jm00249a006
Abstract
Condensation of carvone with olivetol gave a mixture of the two C-5 isomers of 5,6-dihydro-7-hydroxy-2-isopropyl-5-methyl-9-pentyl-2,6-methano-2H-1-benzoxin-4-(3H)-one (2a and 3a) and their positional isomer 4. These ketones were reduced to their respective alcohols, 5a, 6a, and 7a, which were converted to the olefins 8a, 9a, 12 and 13. Compounds 2a and 3a were deoxygenated to 10 and 11a. The benzoxonin 15a was obtained from the condensation of olivetol with a-pinene. The 1,2-dimethylheptyl homologs (on C-9) of 2a, 3a, 5a, 6a, 8a, 9a, 11a, and 15a were also prepared. Several of these compounds produced CNS depression in rats at doses equal to or less than those required for the natural ?6- and ?1-tetrahydrocannibinols.


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