Enantioselective Total Synthesis of Cannabinoids via a Tandem Conjugate Addition/Enolate Alkylation Annulation with Ambiphilic Organoboronates
Jirong Luo, Jeremy A. May
Abstract
-Tetrahydrocannabinol and cannabidiol were synthesized via a tandem enantioselective conjugate addition/enolate alkylation annulation with a novel ambiphilic trifluoroborate in seven steps. A new class of alkenyl and aryl ambiphilic trifluoroborates were synthesized and showed great compatibility with various functional groups, high yields, and excellent enantio- and diastereoselectivity. A novel benzo-fused cannabinoid analogue and tandem quaternary stereocenter-containing reaction products were synthesized with good to excellent enantioselectivity.
Topics & Concepts
AnnulationChemistryConjugateAlkylationEnantioselective synthesisTandemStereochemistryCombinatorial chemistryOrganic chemistryCatalysisMathematicsMathematical analysisMaterials scienceComposite materialAsymmetric Hydrogenation and CatalysisPharmacological Receptor Mechanisms and EffectsCannabis and Cannabinoid Research