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Synthesis of the Tetracyclic Core of Daphnilactone B-Type and Yuzurimine-Type Alkaloids

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journal contribution
posted on 22.02.2016, 12:35 by Guillaume Bélanger, Jonathan Boudreault, François Lévesque
The core of daphnilactone B-type and yuzurimine-type alkaloids was synthesized in only 16 steps from a known β-allyl-γ-butyrolactone. The key sequence of Vilsmeier–Haack cyclization and intramolecular azomethine ylide cycloaddition allowed the construction of, in a single step, three of the five rings common to all alkaloids found in both of these classes with perfect chemocontrol.