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Acid-Catalyzed Aza-Diels−Alder Reactions for the Total Synthesis of (±)-Lapatin B

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journal contribution
posted on 25.05.2007 by Dominique Leca, Francesca Gaggini, Jérôme Cassayre, Olivier Loiseleur, Susan N. Pieniazek, Jennifer A. R. Luft, K. N. Houk
A 5-step total synthesis of microfungal alkaloid (±)-lapatin B has been accomplished via a key 2-aza-Diels−Alder reaction. Brønsted acids catalyze the cycloaddition step and provide improved exo selectivity. This synthetic route has been applied to the construction of related spiro-quinazoline structures.