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Title page for ETD etd-09152011-111420

Type of Document Dissertation
Author Chau, Stephen Thomas
Author's Email Address st.chau@vanderbilt.edu
URN etd-09152011-111420
Title Progess Toward The Total Synthesis of Ammocidin D
Degree PhD
Department Chemistry
Advisory Committee
Advisor Name Title
Gary A. Sulikowski Committee Chair
Brian O. Bachmann Committee Member
Jeffrey N. Johnston Committee Member
Michael P. Stone Committee Member
  • O18 labeling
  • polyketide
  • cyclization
Date of Defense 2011-09-09
Availability unrestricted
The dissertation contained herein describes the synthetic efforts towards the total synthesis of the cytotoxic macrolide ammocidin D. Ammocidin D, isolated by Hayakawa and coworkers in 2009 from the culture broth of Saccharothrix sp. AJ9571 exhibited anti-proliferative activity against the human cancer line MCF7 (IC50. 5.0 µM). Chapter 1 discusses the structural features for the ammocidin class of macrolides, a structural comparison to the related family of apoptolidins and their respective synthetic efforts. Chapter 2 highlights the early approaches towards the pyranose ring system contained within the southern hemisphere. Chapter 3 describes the mechanistic labeling studies and succesful synthesis of the southern hemisphere. Chapter 4 details the synthetic efforts towards the unification between the northern and southern fragments and outlines the final pertinent operations towards the synthesis of ammocidin D.
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