1981
DOI: 10.1002/chin.198113386 View full text |Buy / Rent full text
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Abstract: Im Zusammenhang mit Untersuchungen über die Struktur‐Aktivitäts‐ Beziehungen in der Cannabinoid‐Reihe werden die Cannabinol‐Derivate (VI) synthetisiert.

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“…Treatment of the mixture with boron tribromide provided a corresponding 3:1 mixture of the demethylated products, 5-bornylresorcinol ( 6a ) and 5-isobornylresorcinol ( 6b ). Following a well-established protocol, condensation of the mixture of resorcinols 6a and 6b with (+)- trans - p -mentha-2,8-dien-1-ol ( 7 ) catalyzed by p -toluenesulfonic acid monohydrate gave a 3:1 mixture of the corresponding epimeric Δ 8 -tetrahydrocannabinol analogues, which were separated by flash column chromatography. The major product was bornyl-Δ 8 -THC 8a , which exhibited the characteristic “W” coupling between the C2′-H exo benzylic proton (δ 2.89) and C6′-H exo .…”
Section: Resultsmentioning
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“…Treatment of the mixture with boron tribromide provided a corresponding 3:1 mixture of the demethylated products, 5-bornylresorcinol ( 6a ) and 5-isobornylresorcinol ( 6b ). Following a well-established protocol, condensation of the mixture of resorcinols 6a and 6b with (+)- trans - p -mentha-2,8-dien-1-ol ( 7 ) catalyzed by p -toluenesulfonic acid monohydrate gave a 3:1 mixture of the corresponding epimeric Δ 8 -tetrahydrocannabinol analogues, which were separated by flash column chromatography. The major product was bornyl-Δ 8 -THC 8a , which exhibited the characteristic “W” coupling between the C2′-H exo benzylic proton (δ 2.89) and C6′-H exo .…”
Section: Resultsmentioning