title: Acid-catalyzed aza-Diels-Alder reactions for the total synthesis of (+/-)-lapatin B.
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.
authors.affiliation: SYNGENTA Crop Protection AG, Research Chemistry, CH-4002 Basel, Switzerland.
authors.forename: Dominique
authors.initials: D
authors.lastname: Leca
authors.forename: Francesca
authors.initials: F
authors.lastname: Gaggini
authors.forename: Jérôme
authors.initials: J
authors.lastname: Cassayre
authors.forename: Olivier
authors.initials: O
authors.lastname: Loiseleur
authors.forename: Susan N
authors.initials: SN
authors.lastname: Pieniazek
authors.forename: Jennifer A R
authors.initials: JA
authors.lastname: Luft
authors.forename: K N
authors.initials: KN
authors.lastname: Houk
mesh_terms: D000143:Acids / Q000737:chemistry*; D001372:Aza Compounds / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D011799:Quinazolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000143:Acids; D001372:Aza Compounds; D011799:Quinazolines; C502652:lapatin B