Journal of the Chemical Society. Perkin transactions I p. 2825 - 2829 (1981)
Update date:2022-08-03
Topics: Lithium di-isopropylamide and ethyl chloroformate Propargylation Phase-transfer catalysis Tetra-n-butylammonium hydroxide High-pressure liquid chromatography N.m.r. spectroscopy
Meltzer, Peter C.
Dalzell, Haldean C.
Razdan, Raj K.
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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(1981)