Acid-Catalyzed Aza-Diels−Alder Reactions for the Total Synthesis of (±)-Lapatin B
journal contributionposted on 25.05.2007 by Dominique Leca, Francesca Gaggini, Jérôme Cassayre, Olivier Loiseleur, Susan N. Pieniazek, Jennifer A. R. Luft, K. N. Houk
Any type of content formally published in an academic journal, usually following a peer-review process.
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.