Type of Document	Dissertation
Author	Pierce, Joshua Glenn
URN	etd-12102008-204416
Title	Applications of Allyl and Alkenyl Zirconocenes and Progress Toward the Total Synthesis of Tuberostemonone
Degree	Doctor of Philosophy
Program	Chemistry
School	School of Arts and Sciences
Advisory Committee	Advisor Name Title Peter Wipf Committee Chair Alex Doemling Committee Member Dennis Curran Committee Member Joel Greenberger Committee Member Scott Nelson Committee Member
Keywords	natural products allylic amines immunostimulant chemistry
Date of Defense	2008-11-17
Availability	unrestricted
Abstract This dissertation describes the development of several novel chemical reactions employing allyl and alkenyl zirconocenes. These diverse nucleophiles were employed in the synthesis of a variety of biologically and chemically important molecules. Initially, allyl zirconocenes were employed for the addition to imines, thereby providing rapid access to functionalized homoallylic amines. We were later able to employ alkenyl zirconocenes in both the construction of C-glycosidic bonds and the addition to chiral imines. The power of these transformations was realized by a rapid and stereoselective synthesis of an immunostimulant agent and its analogs. Biological evaluation of these compounds showed encouraging activity against malaria. Small molecule radioprotectant agents have also been developed and show promising potential for therapeutic use. Finally, we were able to install key stereocenters of the Stemona alkaloid tuberostemonone.
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