Abstract:
The first total synthesis of potent cannabinoid, 9?-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.