Enantioselective Total Synthesis of Potent 9β-11-Hydroxyhexahydrocannabinol
Vidyasagar Maurya1, Chandrakumar Appayee1
1Discipline of Chemistry , Indian Institute of Technology Gandhinagar , Palaj, Gandhinagar , Gujarat 382355 , India.
Abstract:
The first total synthesis of potent cannabinoid, 9β-11-hydroxyhexahydrocannabinol, is achieved through a 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 hexahydrocannabinols.
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