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We developed a six-step synthesis of the polycyclic core of vincorine using two cascades of reactions. A cascade of Michael–Mannich reactions was employed for one-pot preparation of a polycyclic intermediate, which was transformed into the desired polycyclic pyrroloindoline ring system using a cascade of methanolysis-N-imine cyclization reactions.
A modular approach to α,β-unsaturated N-aryl ketonitrones has been developed. Specifically, condensation of anilines and enals followed by alkylation of the resulting α,β-unsaturated imines provided N-allyl anilines, which were subjected to oxidation with Oxone® to form α,β-unsaturated N-aryl ketonitrones. This modular approach is general and provides rapid access to diversely substituted α,β-unsaturated...
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