Total Synthesis of Dragocins A–C via Electrochemical Cyclization

03 January 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


The first total synthesis of dragocins A–C, remarkable natural products containing an unusual C-4’oxidized ribose architecture bridged by a polyhydroxylated pyrrolidine, is presented through a route featuring a number of uncommon maneuvers. Several generations towards the target molecules are presented including the spectacular failure of a key C–H oxidation on a late- stage intermediate. The final route features rapid, stereocontrolled access to a densely functionalized pyrrolidine and an unprecedented diastereoselective oxidative electrochemical cyclization to forge the hallmark 9-membered ring. Preliminary studies suggest this electrochemical oxidation protocol is generally useful.


total synthesis

Supplementary materials

Supporting information
procedures, spectra, failed routes


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