AI Article Synopsis
- Researchers successfully synthesized (-)-Δ-tetrahydrocannabinol ((-)-Δ-THC) in eight steps and a related compound in ten steps, starting from a known cinnamic acid.
- They utilized an enantioselective N-heterocyclic carbene (NHC)-catalyzed (4 + 2) annulation process to build a highly enantioenriched cycloxyl β-lactone intermediate.
- The synthesis of (-)-Δ-THC from this intermediate involved multiple steps including alcoholysis, oxidation, decarboxylation, trimethylation, and cyclization.
Article Abstract
Enantioselective syntheses of (-)-Δ-tetrahydrocannabinol ((-)-Δ-THC) and (-)-Δ-THC have been achieved in eight and 10 steps, respectively, from a known cinnamic acid. The syntheses take advantage of an enantioselective N-heterocyclic carbene (NHC)-catalyzed (4 + 2) annulation between donor-acceptor cyclobutanes and cinnamoyl fluorides to construct the highly enantioenriched cycloxyl β-lactone shown. Having constructed this A-ring precursor, elaboration to (-)-Δ-THC is achieved through β-lactone alcoholysis followed by oxidation, dual decarboxylation, trimethylation, and cationic cyclization. Finally, the conversion to (-)-Δ-THC is achieved with established chemistry.
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| http://dx.doi.org/10.1021/acs.orglett.9b00198 | DOI Listing |
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