Author

Holly Grenke

Date Approved

3-16-2015

Date Posted

7-22-2015

Degree Type

Campus Only Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

Committee Member

Harriet Lindsay, Ph.D., Chair

Committee Member

Gregg Wilmes, Ph.D.

Committee Member

Dana Sanford

Abstract

In 1975, Hamberg and associates [1] discovered that human platelets transform arachidonic acid into prostaglandin endoperoxides then further into thromboxane B₂ through the unstable intermediate thromboxane A₂. Pinane thromboxane A₂ is a stable analog of the unstable thromboxane A₂ [2]. Its antithrombotic activity includes the inhibition of platelet aggregation, artery constriction, and thromboxane synthetase [2] and the contraction of induced stomach muscle [3].

This project focuses on the synthesis of pinane thromboxane A₂ via a Suzuki-Miyaura coupling. Advantages of this route include the first example of the use of the Suzuki coupling with this compound, fewer steps within the synthesis and the use of less-toxic chemicals. Accomplishing the Suzuki-Miyaura coupling has proven to be the greatest challenge and will be described in detail (Scheme).

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