Asymmetric synthesis of tetracyclic benzo[a]quinolizidine targets.
We report a novel, facile, and asymmetric approach for the synthesis of polycyclic benzo[ a]quinolizidine targets. In the formation of more functionalized derivatives, we have observed the generation of an iminium ether salt intermediate, formed during an unprecedented retro-Diels-Alder/ N-acyliminium cyclization cascade. The iminium ether intermediate was isolated in good yield, characterized by X-ray crystallography, and subsequently applied as a synthetic building block.
Allin
Steven M
SM
Department of Chemistry, Loughborough University, Loughborough, Leicestershire LE11 3TU, UK. s.m.allin@lboro.ac.uk
Gaskell
Sean N
SN
Elsegood
Mark R J
MR
Martin
William P
WP
D018360:Crystallography, X-Ray; D003500:Cyclization; D003517:Cyclopentanes / Q000737:chemistry; D054837:Quinolizidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D003517:Cyclopentanes; D054837:Quinolizidines