Synthesis and characterization of a compact tricyclic resorcinol from (+)- and (-)-3-pinanol

Tetrahedron Lett. 2012 Aug 29;53(35):4636-4638. doi: 10.1016/j.tetlet.2012.05.165.

Abstract

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.

Keywords: 3-pinanol; cannabinoids; resorcinol.