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Drugs derived from Cannabinoids. Part 8. The Synthesis of Side-chain Analogues of Δ6a,10a-Tetrahydrocannabinol

DOI: 10.1039/P19810002825

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2825 - 2829 (1981)

Update date:2022-08-03

Topics: Propargylation   Phase-transfer catalysis  

Authors:

Meltzer, Peter C.Meltzer, Peter C.

Dalzell, Haldean C.Dalzell, Haldean C.

Razdan, Raj K.Razdan, Raj K.

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Article abstract of DOI:10.1039/P19810002825

The continuation of studies on the synthesis of side-chain analogues of Δ6a,10a-tetrahydrocannabinol as potential therapeutic agents has led to the syntheses of a possible metabolite 1-hydroxy-6,6,9-trimethyl-7,8,9,10-tetrahydro-6H-dibenzopyran-3-ylacetic acid (1) and 2-(1-hydroxy-6,6,9-trimethyl-7,8,9,10-tetrahydro-6H-dibenzopyran-3-yl)pent-4-ynoic acid (17c).The Pechmann condensation of ethyl 4-methyl-2-oxocyclohexane-1-carboxylate with methyl 3,5-dihydroxyphenylacetate (11), followed by Grignard reaction, was utilized to produce the pyran (1).The key step in the synthesis of the propargylacetic acid (17c) was propargylation of the malonate (15) under phase-transfer catalysis.

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