64663-39-4Relevant academic research and scientific papers
Enantioselective Total Synthesis of Potent 9β-11-Hydroxyhexahydrocannabinol
Appayee, Chandrakumar,Maurya, Vidyasagar
, (2020)
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.
Stereochemical Requirements for Cannabinoid Activity
Mechoulam, R.,Lander, N.,Varkony, T. H.,Kimmel, I.,Becker, O.,et al.
, p. 1068 - 1072 (1980)
Several pairs of cannabinoid isomers were synthesized and tested for psychotropic activity in rhesus monkeys.Two regularities were observed: (a) In the absence of the other substituents, the equatorial stereochemistry of the substituent at C-1 determines activity. (b) Two groups of THC-type cannabinoids which differ only in that the chemical groupings in one of them at C-1, C-2 are situated at C-1, C-6 in the other (but retain their stereochemistry) have almost equivalent psychotropic activity.
