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

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摘要
An efficient synthesis of 2,5-di hydrobenzoxepine 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 CM1/CB2 receptors. In vitro assays related to CB1/CB2 receptors did not indicate any activity.
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关键词
2,5-dihydrobenzoxepine, radulanin A, benzoxepin cannabinoids, regioselective allylation, ring-closing metathesis
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