Synthesis and characterization of a compact tricyclic resorcinol from (+)- and (-)-3-pinanol.
Source
Center for Drug Discovery, Northeastern University, 360 Huntington Avenue, 116 Mugar Life Sciences Building, Boston, MA, 02115, USA.
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
- PMID:
- 24052669
- [PubMed]
