Synthesis of cannabidiols via alkenylation of cyclohexenyl monoacetate.
[reaction: see text] Because of the lack of potency binding to the receptors responsible for psychoactivity, cannabidiol has received much attention as a lead compound to develop a nonpsychotropic drug. Herein, we establish a method to access not only cannabidiol but also its analogues. The key reaction is nickel-catalyzed allylation of 2-cyclohexene-1,4-diol monoacetate with a new reagent, (alkenyl)ZnCl/TMEDA, which gives a S(N)2-type product with 94% regioselectivity in good yield.
Kobayashi
Yuichi
Y
Department of Biomolecular Engineering, Tokyo Institute of Technology, Midori-ku, Yokohama, Japan. ykobayas@bio.titech.ac.jp
Takeuchi
Akira
A
Wang
Yong-Gang
YG
D002185:Cannabidiol / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D002384:Catalysis; D053138:Cyclohexenes / Q000737:chemistry*; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry; D015032:Zinc / Q000737:chemistry
D053138:Cyclohexenes; D002185:Cannabidiol; D009532:Nickel; D015032:Zinc