Synthesis of (-)-Delta9-trans-tetrahydrocannabinol: stereocontrol via Mo-catalyzed asymmetric allylic alkylation reaction.
[reaction: see text] Delta9-THC is synthesized in enantiomericaly pure form, where all of the stereochemistry is derived from the molybdenum-catalyzed asymmetric alkylation reaction of the extremely sterically congested bis-ortho-substituted cinnamyl carbonate in high regio- and enantioselectivity.
Trost
Barry M
BM
Department of Chemistry, Stanford University, Stanford, California 94305, USA. bmtrost@stanford.edu
Dogra
Kalindi
K
D000478:Alkylation; D000498:Allyl Compounds / Q000737:chemistry*; D002384:Catalysis; D013759:Dronabinol / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D008982:Molybdenum / Q000737:chemistry*; D013237:Stereoisomerism
D000498:Allyl Compounds; D013759:Dronabinol; D008982:Molybdenum