Enantioselective tandem cyclopropanation/Cope rearrangement of heteroaryldiazoacetates and their applications in natural product synthesis
Olson, Jeremy Price
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The first section of this thesis focuses on the use of heteroaryldiazoacetates in the tandem cyclopropanation/Cope rearrangement. This reaction was found to be highly successful with various heteroaryldiazoacetates including the benzofuran, benzothiophene, and indolyl moieties. This methodology was applied to the formal synthesis of (+)-frondosin B, the total synthesis of (+)-frondosin B, and the total synthesis of epi -liphagal. The second section of this thesis focuses on the expansion of the Rhodium(II) catalyzed cyclopropanation into biological active compounds. These diaryl cyclopropylamines were found to have activity at both the dopamine and serotonin receptors, and are particularly of interest for there specicific 5-HT 2A receptor activity. In this section a series of 12 compounds were synthesized and tested for their biological activity at both the serotonin and dopamine receptors.