Synthesis and characterization of a compact tricyclic resorcinol from (+)- and (-)-3-pinanol.
Resorcinol derivatives are important building blocks in the synthesis of natural products and pharmaceutical compounds including cannabinoids. Here we describe the synthesis and the structural characterization of a key resorcinol which carries a fully restricted bridged bicyclic group. We also report a potential mechanism for the acid catalyzed condensation of (+)- or (-)-3-pinanol with 2,6-dimethoxyphenol. The synthesized resorcinol facilitates the development of novel conformationally restricted cannabinoid analogs.
Center for Drug Discovery, Northeastern University, 360 Huntington Avenue, 116 Mugar Life Sciences Building, Boston, MA, 02115, USA.
Dai
D
Lu
Spyros P
SP
Nikas
Xiu-Wen
XW
Han
Damon A
DA
Parrish
Alexandros
A
Makriyannis
3-pinanol; cannabinoids; resorcinol