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Synthesis 2022; 54(24): 5540-5550
DOI: 10.1055/s-0042-1751361
DOI: 10.1055/s-0042-1751361
paper
Protecting-Group-Free Synthesis of Novel Cannabinoid-Like 2,5-Dihydrobenzoxepines
We acknowledge the financial support from the German Federal Ministry of Education and Research in the program VIPplus for the project CannaCell (03VP06370).
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 metathesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751361.
- Supporting Information
Publikationsverlauf
Eingereicht: 27. Juni 2022
Angenommen nach Revision: 21. Juli 2022
Artikel online veröffentlicht:
13. September 2022
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