A novel synthetic approach to the fasicularin family of marine alkaloids

• Main Author: Marshall, Joseph
• Other Authors: Craig, Donald
• Published: Imperial College London 2014
• Subjects: 540
• Online Access: http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.650705

This thesis is divided into four chapters. The first chapter comprises an introduction to the fasicularin family of marine alkaloids, and a review of previous total syntheses of the members of this class of compounds. This chapter also covers the previous work by Craig et al. on the synthesis of (±)-lepadiformine, and how this influenced our initial approach to the enantioselective synthesis of (-)-lepadiformine. The second chapter details the first part of our investigation into the synthesis of these compounds, including short reviews of diastereoselective aziridination protocols developed by Yoon et al. and Sharpless et al. This section includes the results of this investigation, and discusses the successes and failures of this approach. The third chapter concerns our revised second-generation strategy for the synthesis of (-)-lepadiformine, and includes a review of the decarboxylative Claisen rearrangement, and diastereoselective variants thereof. This section also covers our results and discussion for this revised synthesis. The fourth chapter contains experimental details and characterisation data for all compounds synthesised.