Date of Award
Fall 2013
Degree Type
Dissertation
Degree Name
Doctor of Philosophy (PhD)
Department
Chemistry
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
Abstract
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.
Recommended Citation
Bobinski, Thomas Paul, "Osmium Catalyzed Dihydroxylation And Oxidative Cleavage Of Vinyl Sulfone And Elucidation Of The Vinylsulfone Polypropionate Methodology For The Synthesis Of The C32 Des-Methyl C28-C34 Actin Binding Tail Of Aplyronine A" (2013). Open Access Dissertations. 199.
https://docs.lib.purdue.edu/open_access_dissertations/199