Enantioselective total synthesis of (-)-Δ8-THC and (-)-Δ9-THC via catalytic asymmetric hydrogenation and S(N)Ar cyclization

Org Lett. 2013 Feb 15;15(4):764-7. doi: 10.1021/ol303351y. Epub 2013 Jan 24.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclization
  • Dronabinol / chemical synthesis*
  • Dronabinol / chemistry
  • Hydrogenation
  • Ketones / chemistry
  • Molecular Structure
  • Ruthenium / chemistry
  • Stereoisomerism

Substances

  • Ketones
  • Dronabinol
  • Ruthenium