Defense Date
12-10-2003
Graduation Date
2003
Availability
Immediate Access
Submission Type
thesis
Degree Name
MS
Department
Chemistry and Biochemistry
Committee Chair
Fraser F. Fleming
Committee Member
Omar Steward
Keywords
Oxonitriles
Abstract
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.
Format
Language
English
Recommended Citation
Iyer, P. (2003). Oxonitriles: Cyclizations in Total Synthesis (Master's thesis, Duquesne University). Retrieved from https://dsc.duq.edu/etd/689