ol701689z_si_002.pdf (569.86 kB)
Synthetic Entries to Substituted Bicyclic Pyridones
journal contribution
posted on 2007-12-06, 00:00 authored by Dachen Cheng, Laura Croft, Muna Abdi, Andrew Lightfoot, Timothy GallagherThe synthesis of 6,6- and 5,6-bicyclic pyridone scaffolds has been completed using (i) an intramolecular Mitsunobu reaction and/or (ii) hydrolysis
of a bicyclic pyridinium salt intermediate. Regioselective functionalization of the pyridone ring has been achieved via either direct lithiation
or use of the “halogen dance” reaction. Suzuki coupling then allows introduction of aryl units at C(7)/C(9) or C(8) onto the bicyclic pyridone
scaffold at either an early or late stage in the synthetic sequence. Suzuki couplings involving iodopyridinium intermediates are particularly
effective.