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Title page for ETD etd-12212015-144559

Type of Document Dissertation
Author Wenzler, Marta Elise
Author's Email Address marta.e.wenzler@vanderbilt.edu
URN etd-12212015-144559
Title Progress Toward the Total Synthesis of Upenamide
Degree PhD
Department Chemistry
Advisory Committee
Advisor Name Title
Dr. Gary A. Sulikowski Committee Chair
Alex G. Waterson Committee Member
Brian O. Bachmann Committee Member
Jeffrey N. Johnston Committee Member
  • Formal [4+2] Addition
  • Diels-Alder Cycloaddition
  • Upenamide
  • Phenazine
  • Circadian Clock
  • Staudinger Cyclization
  • Circadian Rhythm
Date of Defense 2015-12-10
Availability unrestricted
Upenamide is a marine alkaloid natural product isolated in 2000 from the marine sponge Echinochalina sp. Protolithospongia. Spectral analysis of the marine alkaloid by the Scheuer group determined the structure upenamide to be one of two possible isomers. Due to limited supply, the overall structure and biological activity of upenamide have not been fully established and are now only available by total synthesis. Thus, chapter 1 details 3-alkylpyridine natural products and related synthetic considerations. Chapter 2 details the isolation and structural elucidation of upenamide and discusses previous synthetic approaches. Chapter 3 discusses our previous synthetic approach and synthetic efforts toward upenamide. Chapter 4 discussed the current synthetic efforts and chapter 5 outlines a strategy for the total synthesis of upenamide. Chapter 6 discusses a medicinal chemistry project discovering new small molecules for understanding the human circadian rhythm.

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