Cannabinoids and cannabinoid acids and their derivatives

• Main Authors: Elliott, Daniel, Berkowitz, Barry A, Barrett, Anthony G
• Format: Patent
• Language: English
• Published: 28.06.2022
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; CHEMISTRY; HETEROCYCLIC COMPOUNDS; HUMAN NECESSITIES; HYGIENE; MEDICAL OR VETERINARY SCIENCE; METALLURGY; ORGANIC CHEMISTRY; PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES

The present invention relates to novel cannabinoids 1 and 2, synthesized from simple starting materials using a cascade sequence of allylic rearrangement, aromatization and, for tetracyclic cannabinoids, further highly stereoselective and regioselective cyclization. These synthesized cannabinoids can more easily be obtained at high purity levels than cannabinoids isolated or synthesized via known methods. The cannabinoids 2 are obtained containing very low levels of isomeric cannabinoids such as the undesirable Δ8-tetrahydrocannabinol. The analogues with variation in aromatic ring substituents, whilst easily synthesized with the new methodology, would be much more difficult to make from any of the components of cannabis oil. Novel compounds of the formulas 3, 4, 5 and 6, as intermediates for the synthesis of the cannabinoids of the formulas 1 and 2 are also disclosed.