Chemistry and Biochemistry
Bayer School of Natural and Environmental Sciences
Fraser F. Fleming
Oxonitriles are versatile synthetic intermediates. The thesis provides a survey of the synthesis and reactions of cyclic oxonitriles followed by an approach to Kuehneromycin A that features oxonitrile chemistry. The discussion presents a synthetic route to the sesquiterpenoid, Kuehneromycin A, using oxonitrile-based methodology. A key feature is a new oxidative cyclization reaction that has been developed as a method for assembling functionalized trans-decalins. The mechanism of this reaction is presented to explain the excellent stereoselectivity. Similarly, a mechanistic analysis of a novel isomerization of quarternary centers is presented in detail.
Iyer, P. (2003). Oxonitriles: Cyclizations in Total Synthesis (Master's thesis, Duquesne University). Retrieved from https://dsc.duq.edu/etd/689