Total Synthesis of (−)-Maximiscin
Kyle S. McClymont, Fengyuan Wang, Amin Minakar, Phil S. Baran
Abstract
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.
Topics & Concepts
Retrosynthetic analysisChemistryEnantioselective synthesisTotal synthesisMesityleneModular designCombinatorial chemistryOrganic synthesisStereochemistryOrganic chemistryProgramming languageCatalysisComputer scienceCatalytic C–H Functionalization MethodsAlkaloids: synthesis and pharmacologyAxial and Atropisomeric Chirality Synthesis