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

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

T-005

Supelco

(−)-trans-Δ⁹-THC solution, 1.0 mg/mL in methanol, ampule of 1 mL, certified reference material, Cerilliant^®

T-047

Supelco

(±)-Δ⁹-THC solution, 100 μg/mL in heptane, ampule of 1 mL, Cerilliant^®

T2386

Sigma-Aldrich

Δ⁹-Tetrahydrocannabinol solution, ethanol solution

T4764

Supelco

Δ⁹-Tetrahydrocannabinol solution, 1.0 mg/mL in methanol, analytical standard, for drug analysis