Lycopodium japonocumin is a common club moss found throughout China used as a traditional medicine to treat contusions, strains, and myasthenia. Although the plant genus of Lycopodium has been the source for over 300 alkaloids, three new alkaloids (Lycojaponicumins A-C) have been isolated from Lycopodium japonocumin. These natural products have biological activity paired with a unique bridged heterocyclic core structure. Lycojapanocumins were seen to inhibit lipopolysaccharide (LPS)-induced pro-inflammatory factors. The purpose of this study is to simplify and synthesize the bicyclic core structure of Lycojaponocumins A-C in an effort to investigate and access the bioactivity of these compounds. The synthetic strategy employed involves an intramolecular 1,3-dipolar cycloaddition between a nitrone and an alkene. The design and synthetic efforts toward the intramolecular cycloaddition precursor will be described.

Synthesis of [2.1.2]-bicyclic heterocycles inspired by Lycojaponicumin natural products

253rd National Meeting (2017)

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