89002-23-3

Upstream product

• 499106-04-6 tert-Butyl-((R)-6-isopropenyl-1-oxa-spiro[2.5]oct-4-en-2-yloxy)-dimethyl-silane 
• 89064-04-0 (1S,2S,6R)-7-oxabicyclo[4.1.0]heptan-2-ol 
• 5503-12-8 L-perillaldehyde 
• 123331-86-2 tert-Butyl-[(R)-4-isopropenyl-cyclohex-2-en-(E)-ylidenemethoxy]-dimethyl-silane 
• 89064-05-1 (3S,4R)-3,4-epoxy-1-cyclohexene 
• 6426-26-2 (S)-cyclohex-2-en-1-ol 
• 89002-21-1 (1R,4R)-4-isopropenyl-2-cyclohexen-1-ol 

Downstream Products

• 123331-90-8 (R)-1-[1,3]Dithian-2-yl-4-isopropenyl-cyclohex-2-enol 
• 123331-88-4 (R)-4-(2-Methyl-oxiranyl)-cyclohex-2-enone 
• 67119-86-2 (4R)-1-(1,3-dithianyl)-4-(2-(2-hydroxypropanyl))-2-cyclohexen-1-ol 
• 123331-89-5 (4R)-1-(1,3-dithianyl)-4-(2-propenylepoxy)-2-cyclohexen-1-ol 
• 28623-60-1 (+/-)-11-hydroxy-Δ⁹-tetrahydrocannabinol 
• 89064-07-3 (4S,5S)-2-(Bis-methylsulfanyl-methylene)-4-isopropenyl-5-methyl-5-vinyl-cyclohexanone 
• 51371-13-2 (3S,4S)-3-Methyl-4-isopropyl-3-vinyl-1-cyclohexanone 
• 89064-06-2 (S)-(+)-4-isopropenyl-3-methyl-2-cyclohexen-1-one 

Relevant academic research and scientific papers

TETRAHYDROCANNABINOID ANTIGENS AND METHOD OF USE

The present invention is directed to Δ8-THC and Δ9-THC compounds useful for the covalent attachment to immunogenic molecules to form antigens for the preparation of specific binding molecules to Δ9-Tetrahydrocannabinol, Δ9-Tetrahydrocannabinoids, Δ8-Tetrahydrocannabinol, and Δ8-Tetrahydrocannabinoids, and their derivatives and metabolites. The present invention is directed to the compounds, their method of preparation, cell lines producing the specific binding molecules, methods of using the antigens to produce the specific binding molecules, and test devices containing the antigens, haptens, or specific binding molecules of the invention.

Synthesis of Racemic and Optically Active Δ9-Tetrahydrocannabinol (THC) Metabolites

The preparation of racemic and optically active Δ9-THC metabolites is described from synthon 13.Racemic synthon 13 is prepared in four steps (46percent) from Danishefsky's diene.Optically active synthon 13 is prepared from perillaldehyde via the enone 22 in six steps (23percent yield).Alternatively, nopinone can be converted to 13 in three steps (50percent yield) via a cyclobutane ring cleavage.The acid-catalyzed condensation of 13 with olivetol (6a) and subsequent conversion to 11-hydroxy and 9-carboxyl Δ9-THC metabolites 2a and 4a is described, as well as the preparation of 1',1'-dimethylheptyl THC analogues 2b, 3b, and 4 b from 5-(1',1'-dimethylheptyl)resorcinol (6c).

An Optically Active Terpenic Synthon for Δ9-Cannabinoids: Synthesis of (-)-11-Hydroxy-Δ9-tetrahydrocannabinol (THC) and Its 1'.1'-Dimethylheptyl Analogue

A facile entry into Δ9-tetrahydrocannabinoids has been achieved via synthon 1, synthesized from (R)-(+)-perillaldehyde in a six-step process (23percent overall yield).

STEREOSELECTIVE TOTAL SYNTHESIS OF (4S)-trans-β-ELEMENONE FROM (S)-2-CYCLOHEXEN-1-OL

Stereoselective first total synthesis of (4S)-trans-β-elemenone was achieved from (S)-2-cyclohexen-1-ol, prepared easily by the asymmetric reduction of 2-cyclohexen-1-one with chiral hydride reagent.