Cannabimovone, a Cannabinoid with a Rearranged Terpenoid Skeleton from Hemp

@article{TaglialatelaScafati2010CannabimovoneAC,
  title={Cannabimovone, a Cannabinoid with a Rearranged Terpenoid Skeleton from Hemp},
  author={Orazio Taglialatela‐Scafati and Alberto Pagani and Fernando Scala and Luciano Petrocellis and Vincenzo Di Marzo and Gianpaolo Grassi and Giovanni Appendino},
  journal={European Journal of Organic Chemistry},
  year={2010},
  volume={2010},
  pages={2067-2072}
}
An investigation of the polar fractions from a nonpsychotropic variety of hemp (Cannabis sativa L.) afforded cannabimovone (6), a polar cannabinoid with a rearranged 2(3→4) abeo-terpenoid skeleton, biogenetically originating from the intramolecular aldolization of a 2',3'-seco-menthanyl precursor. The structure of cannabimovone was elucidated by spectroscopic analysis, whereas attempts to mimic its biogenetic derivation from cannabidiol (2) gave only anhydrocannabimovone (12), the… 
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References

SHOWING 1-8 OF 8 REFERENCES
Synthesis and antitumor activity of quinonoid derivatives of cannabinoids.
TLDR
Three cannabis constituents, cannabidiol (1), Delta(8)-tetrahydrocannabinol (3), and cannabinol (5), were oxidized to their respective para-quinones 2, 4, and 6, and quinone 2 significantly reduced cancer growth of HT-29 cancer in nude mice.
Pheromone Synthesis, CLXXXVI. Synthesis of (1S,2R,5R)‐Bicolorin, the Aggregation Pheromone of Male Beech Bark Beetles (Taphrorychus bicolor), and Its (1R,2R,5S) Isomer
(−)-Bicolorin [(1S,2R,5R)-(−)-2-ethyl-1,5-dimethyl-6,8-dioxabicyclo[3.2.1]octane (1)], the male-produced pheromone of Taphrorychus bicolor, and its (1R,2R,5S) isomer 2 were synthesized by starting
Hashish. I. The structure of cannabidiol.