Citreoviranol (<b>1</b>) is a member of the biologically active resorcyclic lactone family, isolated from the fungus <i>Penicillium citreoviride.</i> In addition to the characteristic resorcyclic lactone moiety, citreoviranol also contains a very rare 6,6 spiroketal lactone. Prior to this work, a total synthesis and biological evaluation of this unique molecule had yet to be undertaken. Gold catalysis has proven to be a mild and efficient method for the synthesis of acid-sensitive spirocyclic heterocycles. Here, we present the total synthesis of citreoviranol using a gold catalysed cyclisation and a novel base induced spiroketalisation.

Total synthesis of citreoviranol

254th National Meeting (2017)

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