Protecting-Group-Free Synthesis of Novel Cannabinoid-Like 2,5-Dihydrobenzoxepines

Gia-Nam Nguyen; Erin Noel Jordan; Oliver Kayser

doi:10.1055/s-0042-1751361

Synthesis, Table of Contents

Synthesis 2022; 54(24): 5540-5550
DOI: 10.1055/s-0042-1751361

paper

Protecting-Group-Free Synthesis of Novel Cannabinoid-Like 2,5-Dihydrobenzoxepines

Gia-Nam Nguyen

^aTechnical Biochemistry, Biochemical and Chemical Engineering, TU Dortmund University, 44227 Dortmund, Germany

^bMINDbioscience GmbH, Emil-Figge-Strasse 76a, 44227 Dortmund, Germany

,

Erin Noel Jordan

^aTechnical Biochemistry, Biochemical and Chemical Engineering, TU Dortmund University, 44227 Dortmund, Germany

,

Oliver Kayser ∗

^aTechnical Biochemistry, Biochemical and Chemical Engineering, TU Dortmund University, 44227 Dortmund, Germany

› Author Affiliations

Abstract

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Abstract

An efficient synthesis of 2,5-dihydrobenzoxepine analogues was developed without using protecting groups. Regioselective allylation was optimized through a recent method utilizing magnesium dicarboxylates. Grubbs catalysts were applied to investigate ring-closing metathesis. The scope of the present route was extended to produce four analogues, which provided novel cannabinoid-like 2,5-dihydrobenzoxepines in sufficient quantities to permit in vitro assays on recombinant CB1/CB2 receptors. In vitro assays related to CB1/CB2 receptors did not indicate any activity.

Key words

2,5-dihydrobenzoxepine - radulanin A - benzoxepin cannabinoids - regioselective allylation - ring-closing metathesis

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References

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