ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
When (-)-Δ8-6a, 10a-trans-THC (THC = Tetrahydrocannabinol), in the form of its diacetate, was irradiated in the presence of oxygen and a sensitizer, followed by reduction with NaBH4, three allylic alcohols were formed: (-)-8α-and (-)-8β-hydroxy-Δ9,11-THC (proportion 3:1) and (-)-9α-hydroxy-Δ7,8-THC. Acetylation of the epimeric 8-hydroxy-compounds with Ac2O/pyridine gave the corresponding diacetates.When (-)-Δ8-6a, 10a-trans-THC, in the form of its tetrahydropyranyl derivative, was heated with m-chloroperbenzoic acid, the two epimeric 8,9-epoxides were formed in equal amounts. These compounds, on treatment with butyllithium, afforded (-)-8α- and (-)-8β-hydroxy-Δ9,11- 6a, 10a-trans-THC-tetrahydropyranylether. After removing the protecting group and treatment with Ac2O/pyridine the same diacetates, as formed by photooxygenation of (-)-Δ8-THC-acetate, were obtained as a 1:1-mixture.On heating these epimeric diacetates to 290° they underwent allylic rearrangement to (-)-11-acetoxy-Δ8-THC-acetate. From this (-)-11-hydroxy-Δ8-6a, 10a-trans-THC was obtained by treatment with LiAlH4.
Additional Material:
6 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19740570112
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