We have previously reported the synthesis of ene-hydrazide from enol triflate and subsequent indolization reaction as a new entry to a regioselective Fischer indole synthesis. In this process, a base-catalyzed intramolecular aza-Michael reaction, in situ trapping of the resulting enolate, and subsequent C-N coupling with phenyl hydrazide afforded the key ene-hydrazide. This new synthetic strategy has been successfully applied to the total synthesis of (+)-aspidospermidine and (-)-tabersonine. For further application, we have envisaged a new synthetic route to (+)-uleine and (-)-tubifolidine by ways of bicyclic carbamates. Formation of enol triflates followed by C-N coupling reactions with phenyl hydrazide and regioselective Fischer indolization under Lewis acidic conditions would selectively give desired indole products. Our progress on the total syntheses of (+)-uleine, (-)-tubifolidine, (-)-tabersonine and polyveoline will be presented.

Kinetically controlled Fischer indolization for the total syntheses of (+)-uleine, (-)-tubifolidine, (-)-tabersonine, and polyveoline

2019 Fall National Meeting

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