Rechoreographing Enterocin’s Ballet of Isomers: Structure Revision of Enterocins C, D, and F

Michael S. Cowled, Ernest Lacey, Peter Karuso, and Andrew M. Piggot

Organic Letters 2021, 22, 9688-9692

Publication Date: December 7, 2020


The tricyclic scaffold of the bacterial polyketide enterocin was recently shown to undergo stereodiversification through a series of abiotic isomerizations, described metaphorically as a “ballet of isomers”. However, some confusion remains regarding the exact nature of these interconversions, with two independent reports proposing different reaction mechanisms and intermediates. Herein, we have rechoreographed enterocin’s ballet of isomers to provide a unified mechanism and revised the structures reported for enterocins C, D, and F.

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