Zamimaphidin A is a novel heptacyclic manzamine-type alkaloid, recently isolated from the Okinawan marine sponge <i>Amphimedon </i>sp. (SS-1231). The structural complexity of this natural product, which processes a 5-hydroxyazatwistane skeleton, coupled with our interest in the application of heteroatom-stabilized nitrenium ions, has led us to initiate a synthesis of this unique antibacterial agent. The key transformation in this endeavor involves generation of the target’s core 2-azabicyclo[2.2.2]octane ring system through the intramolecular oxamidation of an unsaturated <i>O-</i>alkyl hydroxamate. Details of this cyclofunctionalization reaction together with an account of our progress toward the synthesis of zamimaphidin A will be presented.

Progress towards the total synthesis of zamimaphidin A

253rd National Meeting (2017)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.