Progress towards the total synthesis of N-methylwelwitindolinone C isothiocyanate is reported. The tetracyclic core is established by a key alkylation�type 2 intramolecular Diels�Alder cascade reaction, forming three new carbon-carbon bonds and five stereocenters in a single step. Elaboration of the welwitindolinone core includes direct conversion of a ketone to vinyl chloride. Several new dienophiles are also presented.

Progress towards the total synthesis of <i>?N</i>?-methylwelwitindolinone C isothiocyanate

247th National Meeting (2014)

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Progress towards the total synthesis of ?N?-methylwelwitindolinone C isothiocyanate