Synthesis of Key Precursors towards the Lycopodium Alkaloid (+)-Fastigiatine
Christina Owens
Mentors: Scott Rychnovsky, Renzo Samame
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 objective of this project is to prepare two key components: (1) methyl cyclohexanone, and (2) cisdecaline. The cyclohexanone has been made in a multi-step, large-scale synthesis from pulegone. A
diasteroselective Diels-Alder reaction was employed to access the desired bicyclic cis-decaline. In addition,
various reducing agents are being investigated for a selective reduction of the ketone moiety present on
decaline. Further details on the synthesis of fastigiatine as well as future directions will be presented.