136954-91-1

Upstream product

• 80113-04-8 (+/-)-1-(1,3-dithianyl)-4-(1-hydroxy-1-methylethyl)cyclohex-2-enol 
• 104841-04-5 2-(2-Methoxy-4-trimethylsilanyloxy-cyclohex-3-enyl)-propan-2-ol 
• 67119-88-4 (+/-)-9-normethyl-9-(1,3-dithianyl)-Δ⁹-tetrahydrocannabinol 
• 67119-82-8 1-(2-Methoxy-4-trimethylsilanyloxy-cyclohex-3-enyl)-ethanone 
• 67119-85-1 (+/-)-4-(1-hydroxy-1-methylethyl)cyclohex-2-enone 
• 136954-90-0 (+/-)-9-normethyl-9-(1,3-dithianyl)-Δ⁹-tetrahydrocannabiol tert-butyldimethylsilyl ether 
• 52663-85-1 11-oxo-6a,10a-trans-Δ⁹-THC 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 104874-50-2 (+/-)-11-Nor-9-carboxy-Δ⁹-tetrahydrocannabinol 
• 138176-22-4 (+/-)-11-nor-9-carboxy-Δ⁹-tetrahydrocannabinol tert-butyldimethylsilyl ether 

Relevant academic research and scientific papers

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).

Studies on the synthesis of (-)-11-nor-9-carboxy-Δ9-tetrahydrocannabinol (THC) and related compounds: An improved oxidative procedure

A facile procedure is described whereby Δ9-THC aldehydes 4, as their tert-butyldimethylsilyl derivatives, are conveniently oxidized to the corresponding acids with sodium chlorite in the presence of a large excess of 2-methyl-2-butene without isomerization of the Δ9-double bond. Deprotection of the O-protecting group with tetrabutylammonium fluoride in tetrahydrofuran gave the acids 2 in an overall yield of ≥80%. A study of other oxidizing agents and protecting groups demonstrated that this is the procedure of choice for the preparation of 9-carboxy-Δ9-tetrahydrocannabinols.