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

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.

SUBMITTER: Lu D

PROVIDER: S-EPMC3775386 | biostudies-literature | 2012 Aug

REPOSITORIES: biostudies-literature

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

Lu Dai D Nikas Spyros P SP Han Xiu-Wen XW Parrish Damon A DA Makriyannis Alexandros A

Tetrahedron letters 20120801 35

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 restrict ...[more]

PMID: 24052669

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