A synthesis
of carolacton, a myxobacterial natural product that
has profound effects on Streptococcus mutans biofilms, is reported. The synthesis proceeds via a longest linear
sequence of 14 steps from an Evans β-ketoimide and enabled preliminary
evaluations of the effects of late-stage intermediates on S. mutans biofilms. These studies suggest that further
investigations into carolacton’s structure–function
relationships are warranted.
Manganese(III) acetate mediated oxidative radical cyclizations have been used to synthesize a range of densely functionalized and sterically congested cyclopentane-lactones. A number of the resulting lactones contain vicinal all-carbon quaternary stereocenters adjacent to a tertiary benzylic stereocenter and are formed with high levels of stereocontrol.
A mild, diastereoselective synthesis of fused lactone-pyrrolidinones using an oxidative radical cyclization is reported. The methodology is demonstrated in a formal synthesis of (-)-salinosporamide A.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.