Dragocins A-C (1A-1C, Figure ) belong to a peculiar hybrid structural class of secondary metabolites. These intriguing molecules were isolated off the Caribbean coast near Boca del Drago from a marine cyanobacterium and were found to possess modest cytotoxic activity against human lung cancer cells (H-460). Thus far, the only related natural product to the dragocin family is AB-3217A 2 (2) (previously synthesized in 26 steps by Nakata 3 ), an anti-mite substance which features a near identical framework, but lacks the unique C-4' oxidation found on dragocins A-C. Notably, this C-4' functionalization is unprecedented in the natural product space, with the exception of nucleocidin, 4 a C-4' fluorinated nucleoside. Aside from this unusual feature, the dragocins contain an alluring central 9membered ring system which consists of a highly oxidized pyrrolidine harboring four contiguous stereocenters and an electron-rich arene, all cemented upon a polar ribose moiety. In this Communication we disclose a 13-14 step route to dragocins A-C enabled by an unprecedented electrochemical oxidative cyclization.