- Using (+)-carvone to access novel derivatives of (+)-ent-cannabidiol: The first asymmetric syntheses of (+)-ent-CBDP and (+)-ent-CBDV
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(?)-Cannabidiol [(?)-CBD] has recently gained prominence as a treatment for neuro-inflammation and other neurodegenerative disorders; interest is also developing in its synthetic enantiomer, (+)-CBD, which has a higher affinity to CB1/CB2 receptors than the natural stereoisomer. We have developed an inexpensive, stereoselective route to access ent-CBD derivatives using (+)-carvone as a starting material. In addition to (+)-CBD, we report the first syntheses of (+)-cannabidivarin, (+)-cannabidiphorol as well as C-6/C-8 homologues.
- Golliher, Alexandra E.,Tenorio, Antonio J.,Dimauro, Nina O.,Mairata, Nicolas R.,Holguin, F. Omar,Maio, William
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supporting information
(2021/02/20)
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- Biosynthesis of primin and miconidin and its derivatives
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Numerous 2-methoxy-6-n-alkyl-1,4-benzoquinones with interesting biological activities have been found as constituents of plants and plant seeds. The most prominent is primin, the n-pentyl derivative, which is stored in trichomes on leaves and stems of Primula obconica and is responsible for primrose dermatitis. The biosynthesis of primin was studied by feeding experiments with radioactively labelled precursors and unlabelled homologues. Copyright
- Horper, Wolfgang,Marner, Franz-Josef
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p. 451 - 456
(2007/10/03)
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- BIOLOGICALLY ACTIVE PHENOLIC METABOLITES OF A VERTICICLADIELLA SPECIES
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The metabolites produced when a Verticicladiella species (Canadian Forestry Service strain C728), the causative agent of the black stain root disease of many conifers, is grown in liquid culture have been investigated.Orcinol, orcinol monomethyl ether, 1,3,6,8-tetrahydroxyanthraquinone, and the α-L-rhamnopyranosides of orcinol and orcinol methyl ether have been isolated and indentified.Orcinol methyl ether and its rhamnoside both show antibacterial activity and orcinol methyl ether also inhibits the growth of pine germlings.The general antibacterial activity of 5-alkylresorcinols and their monomethyl ethers is reported.-Key Word Index-Verticicladiella sp.; Deuteromycontina; blue-stain fungus; phytotoxin; phenols; methylorcinol rhamnoside; phenol monomethyl ethers; antiseptics.
- Ayer, William A.,Browne, Lois M.,Lovell, Sarah H.
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p. 2267 - 2272
(2007/10/02)
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