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

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 synthesis of the other potent hexahy-drocannabinols.