SYNTHESIS OF 6,6- AND 7,7-DIFLUORO-1-ACETAMIDOPYRROLIZIDINES AND THEIR OXIDATION CATALYZED BY THE NONHEME Fe OXYGENASE LolO

Nabin Panth
One of the remarkable steps in loline alkaloid biosynthesis is the installation of an ether bridge between two unactivated C atoms in 1-exo-acetamidopyrrolizidine (AcAP). LolO, a 2-oxoglutarate-dependent nonheme Fe oxygenase, catalyzes both the hydroxylation of AcAP and the resulting alcohol's cycloetherification to give N-acetylnornoline (NANL). The mechanism of hydroxylation is well understood, but the mechanism of the oxacyclization is not. I synthesized difluorinated analogs of AcAP in an attempt to further understand the mechanism of...
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