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Open Access Publications from the University of California

Synthetic Studies Toward the Total Synthesis of Maklamicin and Related Spirotetronate Polyketides

  • Author(s): Lacoske, Michelle
  • Advisor(s): Theodorakis, Emmanuel A.
  • et al.

Spirotetronate polyketides are naturally occurring natural products that are highlighted by their complex structures and intruiging biological activities. Chapter 1 emphasizes the importance of this class of natural products from their synthetic endeavors to their molecular targets as cancer therapeutics. Chapter 2 discusses the synthesis of the decalin moiety for the class of spirotetronate polyketides. The synthesis is highlighted by an intramolecular Diels-Alder reaction (IMDA) that proceeds through an energetically unfavored endo-axial transition state. Chapter 3 examines synthetic efforts toward the total synthesis of maklamicin and the difficulties in the synthesis of spirotetronates polyketides in the laboratory. Chapter 4 elaborates upon a general synthetic strategy towards the synthesis of this class of natural products addressing the main struggles faced towards the total synthesis of maklamicin. This strategy also opens a general strategy to potentially synthesize spirotetronate polyketides with varying sizes of the macrocyclic motif.

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