Date Approved
3-16-2015
Date Posted
7-22-2015
Degree Type
Campus Only Thesis
Degree Name
Master of Science (MS)
Department or School
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).
Recommended Citation
Grenke, Holly, "Synthesis of pinane thromboxane A₂ via suzuki-miyaura coupling" (2015). Master's Theses and Doctoral Dissertations. 610.
https://commons.emich.edu/theses/610