The Stereoselective Total Synthesis of the Elusive Cephalosporolide F

J Org Chem. 2023 Apr 7;88(7):4880-4885. doi: 10.1021/acs.joc.3c00251. Epub 2023 Mar 29.

Abstract

Here we report a seven-step protecting-group-free stereoselective total synthesis of the elusive (+)-cephalosporolide F from d-glucose. A microwave-assisted reaction between the Meldrum's acid and the d-glucose to the respective octono-1,4-lactone derivative, and a low temperature visible-light photoredox spirocyclization of a chiral N-alkoxyphthalimide to ceph F, are the two key chemical reactions that allowed the accomplishment of this unprecedented feat under an environmentally friendly processes.