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

RÉSUMÉ

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.