The 2-azabicyclo[3.3.1]nonane ring system lies at the heart of a prestigious array of natural products, including members of the Madangamine, Strychnos, Uleine, and Akuammiline alkaloid families, as well as countless opiates and morphinans. We report our progress towards the synthesis of the heptacyclic core of zamamiphidin A, a manzamine related alkaloid from an Okinawan marine sponge Amphimedon sp. Central to this approach is the iodine(III)-mediated intramolecular oxamidation of an unsaturated O-methyl hydroxamate, which proceeds in high yields and with complete regioselectivity to generate the 2-azabicyclo[3.3.1]nonane core of this natural product

Progress towards the heptacyclic core of core of zamamiphidin A

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