- CANNABINOID DERIVATIVES, PRECURSORS AND USES
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The present disclosure relates to new cannabinoid derivatives and precursors and processes for their preparation. The disclosure also relates to pharmaceutical and analytical uses of the new cannabinoid derivatives.
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- Improved accessibility to the desoxy analogues of Δ9- tetrahydrocannabinol and cannabidiol
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Desoxy analogues of Δ9-tetrahydrocannabinol (THC) and cannabidiol (CBD) have been reported to provide a novel mode of analgesia whilst avoiding the psychotropic side effects associated with most cannabinoid drugs. A detailed and improved synthesis of desoxy THC, desoxy CBD and didesoxy CBD is reported here. The key improvements include a concentration-dependent boron trifluoride mediated electrophilic aromatic substitution which was used to synthesize both THC and CBD analogues. The synthetic route is general and could be applied to the development of a library of modified desoxy THC and desoxy CBD analogues.
- Wilkinson, Shane M.,Price, Jason,Kassiou, Michael
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supporting information
p. 52 - 54
(2013/02/22)
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- Asymmetric addition of diethylzinc to aldehydes catalyzed by β-amino alcohols derived from limonene oxide
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A series of β-amino alcohols, conveniently prepared from limonene oxide, were evaluated as catalysts for the enantioselective addition of dialkylzinc to benzaldehyde. These limonene-based amino alcohols are of particular interest because they are easily synthesized in both enantiomeric forms. Ethylation of benzaldehyde using diethylzinc and catalyzed by limonene derived amino alcohols proceeded with enantioselection of up to 87% ee. This is an unusually high level of induction for amino alcohols possessing a trans relationship between the amino and alcohol functionalities. Both enantiomers of 1-phenyl-1-propanol can be synthesized with equal control since both enantiomers of the chiral catalyst are readily available. When (1S,2S,4R)-limonene amino alcohols are used as chiral catalysts, (R)-1-phenyl-1-propanol is obtained as the major product. A plausible mechanism is proposed to explain the facial selectivity determining the asymmetric induction observed in these reactions.
- Steiner, Derek,Sethofer, Steven G.,Goralski, Christian T.,Singaram, Bakthan
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p. 1477 - 1483
(2007/10/03)
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- A New Synthesis of (-)-Furodysin
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A synthesis of furodysin from trans-limonene oxide involves transformation into the phenylcarbamate of 2,8-menthadien-1-ol, allylic displacement with lithium di(β-furylmethyl)cuprate, and cyclization.
- Ho, Tse-Lok,Lee, Kwang-Yuan
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p. 947 - 948
(2007/10/02)
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- Identification and Synthesis of (Z)-(1'S,3'R,4'S)(-)-2-(3',4'-Epoxy-4'-methylcyclohexyl)-6-methylhepta-2,5-diene, the Sex Pheromone of the Southern Green Stinkbug, Nezara viridula (L.)
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The sex pheromone of the male green stinkbug, Nezera viridula (L.) has been shown to be a novel epoxybisabolene (Z)-(1'S,3'R,4'S)(-)-2-(3',4'-epoxy-4'-methylcyclohexyl)6-methylhepta-2,5-diene, whose structure has been confirmed by spectroscopic studies and synthesis of the eight possible stereoisomers.
- Baker, Raymond,Borges, Miguel,Cooke, Nigel G.,Herbert, Richard H.
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p. 414 - 416
(2007/10/02)
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