Preparation of Essential Precursors Towards the Total Synthesis of the Lycopodium Alkaloid

Sunday, 15 February 2015
Exhibit Hall (San Jose Convention Center)
Christina Owens, University of California, Irvine, Irvine, CA
Alkaloids found in the Lycopodium family are characterized by unique and complex molecular structures and spark interest due to their diverse biological activities. The use of lycopodium alkaloids in pharmacological research is limited due to the lack of useful synthetic methods to supply material for medicinal studies. The Rychnovsky group is investigating methods for the synthesis of the lycopodium alkaloid, (+)-fastigiatine. The main two objectives of this project is based on two key component are: (1) preparation of a functionalized cis-decaline and (2) synthesis of amino acid-derived coupling partners. The decaline system has been made in a multi-step, large-scale synthesis from (R)-pulegone. In addition, various reducing agents were investigated for a selective reduction of the ketone moiety present on decalin. Once reduced, the resulting alcohol was protected and is ready for further modifications. Additional details on the synthesis of the precursors of fastigiatine as well as future directions will be presented.