A BIOMIMETIC SYNTHESIS OF 1Δ-TETRAHYDROCANNABIOL

DOI: 10.1016/S0040-4039(00)87498-5

Source and publish data:

Tetrahedron Letters p. 2935 - 2938 (1982)

Update date:2022-08-11

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Authors:

Chan, T. H.

Chaly, T.

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Article abstract of DOI:10.1016/S0040-4039(00)87498-5

Condensation of 1,3-bis(trimethylsiloxy)-1-methoxybutadiene with the acid chloride 12 gave methyl olivetolate (13).Condensation of 13 with (+)-p-mentha-2,8-dien-1-ol gave methyl ¹Δ-tetrahydrocannabiolate (14) in 55percent isolated yield.Alkaline hydrolysis of 14 gave ¹Δ-tetrahydrocannabinol (1, ¹Δ-THC).The synthesis is patterned after the biogenesis of 1.

Full text of DOI:10.1016/S0040-4039(00)87498-5

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