Author

Pravin Iyer

Defense Date

12-10-2003

Graduation Date

2003

Availability

Immediate Access

Submission Type

thesis

Degree Name

MS

Department

Chemistry and Biochemistry

School

Bayer School of Natural and Environmental Sciences

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

PDF

Language

English

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