Acid-Catalyzed Aza-Diels−Alder Reactions for the Total Synthesis of (±)-Lapatin B
The Journal of Organic Chemistry2007Vol. 72(11), pp. 4284–4287
Citations Over TimeTop 12% of 2007 papers
Dominique Leca, Francesca Gaggini, Jérôme Cassayre, Olivier Loiseleur, Susan N. Pieniazek, Jennifer A. R. Luft, K. N. Houk
Abstract
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.
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