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

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posted on 2023-01-17, 22:10 authored by Abir Bhattacharjee, Mikhail V. Gerasimov, Sam Dejong, Duncan WardropDuncan 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.

Funding

Synthesis Through N-Acylinitrenium Ion Cyclization | Funder: National Institutes of Health (National Institute of General Medical Sciences) | Grant ID: R01GM067176

History

Citation

Bhattacharjee, A., Gerasimov, M. V., Dejong, S.Wardrop, D. J. (2017). Oxamidation of Unsaturated O-Alkyl Hydroxamates: Synthesis of the Madangamine Diazatricylic (ABC Rings) Skeleton. Organic Letters, 19(24), 6570-6573. https://doi.org/10.1021/acs.orglett.7b03283

Publisher

American Chemical Society (ACS)

Language

en

issn

1523-7060