Total Synthesis of (−)-Maximiscin

A short,
enantioselective synthesis of (−)-maximiscin, a
structurally intriguing metabolite of mixed biosynthetic origin, is
reported. A retrosynthetic analysis predicated on maximizing ideality
and efficiency led to several unusual disconnections and tactics.
Formation of the central highly oxidized pyridone ring through a convergent
coupling at the end of the synthesis simplified the route considerably.
The requisite building blocks could be prepared from feedstock materials
(derived from shikimate and mesitylene). Strategies rooted in hidden
symmetry recognition, C–H functionalization, and radical retrosynthesis
played key roles in developing this concise route.