Journal
ORGANIC LETTERS
Volume 6, Issue 14, Pages 2357-2360Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol049316s
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A new approach to prepare 1,5-methano-2,3,4,5-tetrahydro-1H-3-benzanepine (1) is discussed. This strategy utilized a tandem Michael addition and Pd-catalyzed cyclization to afford cyanobenzofulvene acetal 13. This indene intermediate (13) was subjected to hydrogenolysis to provide an amino ester (12) and was cyclized with base to afford lactam 5. The lactam (5) was reduced with borane to afford the desired benzazepine (1).
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