Date of Award

Fall 2013

Degree Type


Degree Name

Doctor of Philosophy (PhD)



First Advisor

Philip L. Fuchs

Committee Chair

Philip L. Fuchs

Committee Member 1

Paul Wenthold

Committee Member 2

Mark Lipton

Committee Member 3

Mahdi Abu- Omar


A general methodology for the generation of dipropionate functionalities using cyclic 7-membered vinylsulfones has been devised for the purpose of synthesizing polyketide natural products such as aplyronine A. Final oxidative cleavage via ozonolysis has been shown to be difficult providing variable yields. Furthermore, elegant synthesis of the C28-C34 segment of the aplyronine A actin binding tail has proved elusive. Utilization of OsO4 and catalytic citric acid has led to a methodology whereby harsh ozonolysis procedures can be mostly avoided. A reengineering of the vinylsulfone polypropionate methodology in conjunction with osmylation has been found to provide the actin binding tail under mild high yielding conditions. These discoveries will be key in developing a methodology for providing highly complex large scale substrates for the synthesis of asymmetric natural products.