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Open Access Publications from the University of California

Efforts Towards the Synthesis of Ceylonamide A via a Stereocontrolled Polyene Cyclization

  • Author(s): Coyne, Glynis Longworth
  • Advisor(s): Vanderwal, Christopher D
  • et al.

This thesis describes efforts made towards the synthesis of ceylonamide A via a stereocontrolled cationic polyene cyclization. Chapter 1 provides background on the ceylonamide family of natural products and reviews the use of cationic polyene cyclizations as a general synthetic approach. This chapter reviews a particular cyclization methodology recently reported by the Vanderwal group which allows for a new mode of access to specific polycyclic structural motifs. A novel application of this technology is proposed towards the synthesis of the bioactive diterpene ceylonamide A.

Chapter 2 discusses the efforts made towards the synthesis of ceylonamide A. The preparation of a key intermediate and attempts to carry out the desired cyclization are described. In addition, control studies to investigate the confounding factors of this cyclization are detailed, along with the synthesis of the substrates utilized in each experiment.

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