Synthesis of (-)-Delta9-trans-tetrahydrocannabinol: stereocontrol via Mo-catalyzed asymmetric allylic alkylation reaction

Org Lett. 2007 Mar 1;9(5):861-3. doi: 10.1021/ol063022k. Epub 2007 Feb 1.

Abstract

[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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Allyl Compounds / chemistry*
  • Catalysis
  • Dronabinol / chemical synthesis*
  • Dronabinol / chemistry
  • Molecular Structure
  • Molybdenum / chemistry*
  • Stereoisomerism

Substances

  • Allyl Compounds
  • Dronabinol
  • Molybdenum