Fused bicyclic dihydropyrans can be prepared by a four step procedure which converted cyclic epoxides and a vinyl grignard reagent into the disubstituted cyclic compounds, trans-2-ethenylcyclohexanol and trans-2-ethenylcyclopentanol. These compounds can be directly converted into fused bicyclic vinyl boronic half acids by the use of the first generation Grubbs catalyst and equal equivalents of the trans cyclic alcohol and vinyl boronic acid. The Suzuki coupling reaction was performed on the organoboronic half acid and ethyl cis-3-iodoacrylate  with the aid of a palladium catalyst.  Automated column chromatography was utilized to separate the coupled compound from the halide acrylate. The coupled compound was refluxed with NaH in order to produce the fused bicyclic dihydropyran. The resulting NMR showed that progress was made in route to making fused bicylic dihydropyrans; however, further work needs to be done in order to obtain a purer compound.

Synthesis of fused bicyclic dihydropyrans

243rd National Meeting (2012)

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