- Enantioselective total synthesis of (-)-Δ8-THC and (-)-Δ9-THC via catalytic asymmetric hydrogenation and S(N)Ar cyclization.
Enantioselective total synthesis of (-)-Δ8-THC and (-)-Δ9-THC via catalytic asymmetric hydrogenation and S(N)Ar cyclization.
Organic letters (2013-01-26)
Li-Jie Cheng, Jian-Hua Xie, Yong Chen, Li-Xin Wang, Qi-Lin Zhou
PMID23346909
ABSTRACT
The highly efficient asymmetric total syntheses of (-)-Δ(8)-tetrahydrocannabinol ((-)-Δ(8)-THC) (13 steps, 35%) and (-)-Δ(9)-tetrahydrocannabinol ((-)-Δ(9)-THC) (14 steps, 30%) have been developed by using ruthenium-catalyzed asymmetric hydrogenation of racemic α-aryl cyclic ketones via dynamic kinetic resolution and intramolecular S(N)Ar cyclization.
MATERIALS
Product Number
Brand
Product Description
Supelco
(−)-trans-Δ9-THC solution, 1.0 mg/mL in methanol, ampule of 1 mL, certified reference material, Cerilliant®
Supelco
Δ9-Tetrahydrocannabinol solution, 1.0 mg/mL in methanol, analytical standard, for drug analysis