A biomimetic synthesis of Δ1-tetrahydrocannabinol

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Abstract

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 Δ1-tetrahydrocannabinolate (14) in 55% isolated yield. Alkaline hydrolysis of 14 gave Δ-tetrahydrocannabinol (1, Δ1-THC). The synthesis is patterned after the biogenesis of 1. © 1982.

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Chan, T. H., & Chaly, T. (1982). A biomimetic synthesis of Δ1-tetrahydrocannabinol. Tetrahedron Letters, 23(29), 2935–2938. https://doi.org/10.1016/S0040-4039(00)87498-5

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