The tricyclic core common to azabicyclononane members of the aeruginosin family of natural products is densely functionalized with six stereogenic centers and incorporates glycosyl as well as peptide side chains at its periphery. The biological activity along with the sheer complexity of the structure renders these notable as targets for synthesis studies. We report a rapid enantioselective synthesis of the fully functionalized azabicyclononane (Abn) core common to the banyasides, suomilide and spumigin HKVV relying on a novel oxabicyclic building block. In addition we developed an entry into the Aeruginosin class of natural products containing the common carboxyoctahydroindole core (Choi) relying on the same oxabicyclic building block via a novel Lewis acid mediated nucleophilic oxabicyclic ring opening method, discovered in the course of the synthetic studies towards the Banyasides.

Synthetic access to members of the Aeruginosin family of natural products relying upon a novel oxabicyclic building block

240th National Meeting (2010)

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