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