Enantioselective Total Synthesis of Potent 9β-11-Hydroxyhexahydrocannabinol.

@article{Maurya2019EnantioselectiveTS,
  title={Enantioselective Total Synthesis of Potent 9$\beta$-11-Hydroxyhexahydrocannabinol.},
  author={Vidyasagar Maurya and Chandrakumar Appayee},
  journal={The Journal of organic chemistry},
  year={2019}
}
The first total synthesis of potent cannabinoid, 9β-11-hydroxyhexahydrocannabinol is achieved through proline catalyzed inverse-electron-demand Diels-Alder reaction. Using this asymmetric catalysis, the cyclohexane ring is constructed with two chiral centers as a single diastereomer with 97% ee. The creation of the third chiral center and benzopyran ring is demonstrated with the elegant synthetic strategies. This mild and efficient synthetic methodology provides a new route for the asymmetric… 
3 Citations
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References

SHOWING 1-10 OF 44 REFERENCES
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
Stereodivergent total synthesis of Δ9-tetrahydrocannabinols.
All four stereoisomers of Δ(9)-tetrahydrocannabinol (Δ(9)-THC) were synthesized in concise fashion using stereodivergent dual catalysis. Thus, following identical synthetic sequences and applying
Catalytic Asymmetric Synthesis of 3,4-Disubstituted Cyclohexadiene Carbaldehydes: Formal Total Synthesis of Cyclobakuchiols A and C.
TLDR
The first catalytic approach for the asymmetric synthesis of 3,4-disubstituted cyclohexadiene carbaldehydes through an inverse-electron-demand Diels-Alder reaction is described and is successfully applied for the formal total synthesis of cyclobakuchiol A, an antipyretic and anti-inflammatory agent, and cyclobAKuchiol C.
Enantioselective Total Synthesis of (-)-Δ9-Tetrahydrocannabinol via N-Heterocyclic Carbene Catalysis.
TLDR
The syntheses take advantage of an enantioselective N-heterocyclic carbene (NHC)-catalyzed annulation between donor-acceptor cyclobutanes and cinnamoyl fluorides to construct the highly enantioenriched cycloxyl β-lactone shown.
Total Synthesis of (-)-Marinisporolide C.
The first total synthesis of (-)-marinisporolide C is described, which establishes unequivocally the relative and absolute configuration of this oxopolyene macrolide. Key features of this synthesis
Synthesis of (-)-.DELTA.9-6a,10a-trans-tetrahydrocannabinol. Boron trifluoride catalyzed arylation by a homocuprate
L'arylation de l'acetate du p-menthadiene-2,8 ol-1 catalysee par BF 3 conduit au dimethylether de cannabidiol trans(-), qui est transforme en tetrahydrocannabinol trans
Enantioselective total synthesis of (-)-Δ8-THC and (-)-Δ9-THC via catalytic asymmetric hydrogenation and S(N)Ar cyclization.
TLDR
The highly efficient asymmetric total syntheses of (-)-Δ(8)-tetrahydrocannabinol (THC) and (-)- 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.
Short and Divergent Total Synthesis of (+)-Machaeriol B, (+)-Machaeriol D, (+)-Δ(8)-THC, and Analogues.
Short and highly efficient stereoselective syntheses provide machaeriols and cannabinoids in a divergent approach starting from a common precursor, commercially available (S)-perillic acid. Key
Structure--activity studies on tetrahydro- and hexahydrocannabinol derivatives.
A series of tetrahydro- and hexahydrocannabinol derivatives was prepared in which the substituents at position 9 were varied. These compounds were evaluated in mice for their effects on locomotor
Synthesis of tetrahydrocannabinols based on an indirect 1,4-addition strategy.
TLDR
An indirect method consisting of iodination of the cyclohexenones at the alpha position and reaction of the alpha-iodo-beta-aryl-cylohexanones with EtMgBr to generate magnesium enolates showed a high reactivity toward ClP(O)(OEt)(2) to furnish enol phosphates.
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