Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Total Synthesis of Lycopladine A and Carinatine A via a Base-Mediated Carbocyclization

Total Synthesis of Lycopladine A and Carinatine A via a Base-Mediated Carbocyclization
Felix W. W. Hartrampf, Dirk Trauner
A concise, enantioselective synthesis of lycopladine A and carinatine A is presented. Our synthetic approach hinges on the recently developed mild carbocyclization of ynones to furnish the hydrindane core of the alkaloids. Their pyridine ring was efficiently installed using the Ciufolini method. Both heterocycles of carinatine A, a rare naturally occurring nitrone, were formed in a single operation.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00908

DOI: 10.1021/acs.joc.7b00908

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