Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Syntheses of Cannabinoid Metabolites: Ajulemic Acid and HU-210

Version 1 : Received: 19 December 2023 / Approved: 20 December 2023 / Online: 20 December 2023 (08:34:17 CET)

A peer-reviewed article of this Preprint also exists.

Shao, W.; Liao, P.; Zhang, X.; Fan, B.; Chen, R.; Chen, X.; Zhao, X.; Liu, W. Syntheses of Cannabinoid Metabolites: Ajulemic Acid and HU-210. Molecules 2024, 29, 526. Shao, W.; Liao, P.; Zhang, X.; Fan, B.; Chen, R.; Chen, X.; Zhao, X.; Liu, W. Syntheses of Cannabinoid Metabolites: Ajulemic Acid and HU-210. Molecules 2024, 29, 526.

Abstract

Cannabinoid metabolites have been reported to be more potent than the parent compounds. Among them, Ajulemic acid (AJA) is a synthetic analogue of Δ9-THC-11-oic which will be a good template structure for discovery of more potent analogues. Herein, we optimized the key allylic oxidation step to introduce the C-11 hydroxy group with high yield. And a series of compounds were prepared with this condition applied including HU-210, 11-Nor-Δ8-Tetrahydrocannabinol-9-carboxylic acid and Δ9-THC-COOH.

Keywords

Phytocannabinoids; Metabolites; Ajulemic acid; Riley oxidation

Subject

Chemistry and Materials Science, Organic Chemistry

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