A BIOMIMETIC SYNTHESIS OF 1Δ-TETRAHYDROCANNABIOL

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.