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Oxamidation of Unsaturated O‑Alkyl Hydroxamates: Synthesis of the Madangamine Diazatricylic (ABC Rings) Skeleton

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journal contribution
posted on 28.11.2017, 13:59 by Abir Bhattacharjee, Mikhail V. Gerasimov, Sam DeJong, Duncan J. Wardrop
A novel approach to the diazatricyclic madangamine ABC ring system and the synthesis of an advanced, differentially protected intermediate for the synthesis of madangamine D is reported. Central to the success of this approach is the iodine­(III)-mediated intramolecular oxamidation of an unsaturated O-methyl hydroxamate, a π–N+-type cyclization which proceeds in high yield and with complete regioselectivity to generate the 2-azabicyclo[3.3.1]­nonane (morphan) system encompassing rings A and C.