Synthetic methods towards the core tricyclic ring system of pradimicin A

• Author / Creator

  Zilke, Laura Carolyn

• The pradimicins are natural products that are both structurally intriguing to a synthetic chemist and possess biological activity as antifungal and antiviral agents. Our interest towards designing a synthetic route for these compounds and various analogues was sparked by the potential to produce a library of efficient carbohydrate receptors. The initial synthetic approach towards pradimicin A involved a model study of the synthesis of the core tricyclic ring system. This route featured an alkoxyallylboration, ring closing enyne metathesis and Diels-Alder cycloaddition. Chapter 2 describes the efforts towards synthesizing starting materials and the enyne metathesis precursor, which includes a mono-protected trans-diol. Chapter 3 focuses on the reaction conditions and various substrates that were tested for the ring closing enyne metathesis reaction. The optimal route found for the synthesis of the tricyclic ring system featured a one-pot palladium catalyzed cycloisomerization, Diels-Alder reaction and aromatization.

• Subjects / Keywords

  • Carbohydrate binding agents
  • Synthesis
  • Organic chemistry
  • Natural products
  • Pradimicin A

• Graduation date

  Fall 2011

• Type of Item

  Thesis

• Degree

  Master of Science

• DOI

  https://doi.org/10.7939/R3N58CV3Q

• License

  This thesis is made available by the University of Alberta Libraries with permission of the copyright owner solely for non-commercial purposes. This thesis, or any portion thereof, may not otherwise be copied or reproduced without the written consent of the copyright owner, except to the extent permitted by Canadian copyright law.