Enantioselective total synthesis of (-)-Δ8-THC and (-)-Δ9-THC via catalytic asymmetric hydrogenation and S(N)Ar cyclization.
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.
State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China.
Li-Jie
LJ
Cheng
Jian-Hua
JH
Xie
Yong
Y
Chen
Li-Xin
LX
Wang
Qi-Lin
QL
Zhou
D002384:Catalysis; D003500:Cyclization; D013759:Dronabinol / Q000138:chemical synthesis* / Q000737:chemistry; D006865:Hydrogenation; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism
D007659:Ketones; D013759:Dronabinol; D012428:Ruthenium