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Toward the Synthesis of the Magellaninone- and Lycopladine-type Lycopodium Alkaloids


This dissertation describes our strategy toward the synthesis of a variety of fawcettimine–type Lycopodium alkaloids. The first section focuses on the classification, structure, and historical significance of these natural products. This section also includes a proposal for their biosynthesis and a survey of the biological activities of the members of this class.

The second section describes our work toward magellanine, magellaninone, and paniculatine. Two existing syntheses of these molecules are discussed, along with the strategy that we chose to employ in our work. We first pursue the synthesis of these natural products using a C4 pyridine C–H functionalization strategy that is based on precedent by the Fagnou and Echavarren groups. We then describe a C3 pyridine C–H functionalization approach that has more diverse methodological inspiration, although the original synthetic disconnection strategy derives from work done by the Jin Quan Yu group. Both of these synthetic endeavors are detailed herein.

Finally, the third section covers our efforts toward the synthesis of lycopladines B, C, and D. We describe our “Heathcock–inspired“ cascade approach toward the divergent synthesis of these three natural products. In this work, we have pursued the synthesis of a number of different substrates. We conclude with a summary of how this approach has evolved into a number of other projects within our group.

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