1 research outputs found
Base-Mediated Cascade Cyclization: Stereoselective Synthesis of Benzooxazocinone
A new strategy for
the synthesis of the oxa-azabicyclo[3.3.1]Ânonane
subunit, a component of the naucleamide E core structure, has been
developed. This annulation reaction between 1-substituted 3,4-dihydroisoquinolines
and coumarin derivatives conveniently affords the oxa-azabicyclo[3.3.1]Ânonane
framework via a base-mediated cascade cyclization under aqueous conditions.
The value of this work lies in the efficient formation of the oxa-azabicyclo[3.3.1]Ânonane
skeleton via a process whereby all the C–C, C–O, and
C–N bond formations occur in a single chemical operation. In
addition, the subsequent ring opening of these compounds furnished
pyridoisoquinoline derivatives