Depsipeptide synthesis using a late-stage Ag(i)-promoted macrolactonisation of peptide thioamides
Sadegh Shabani, Craig A Hutton
CHEMICAL COMMUNICATIONS | ROYAL SOC CHEMISTRY | Published : 2021
Macrolactonisation of peptides to generate cyclic depsipeptides is often challenging due to the low nucleophilicity of hydroxyl groups, epimerisation, cyclodimerisation, and potential acyl transfer reactions of the ester. Herein, we report a novel macrolactonisation strategy employing a Ag(i)-promoted conversion of peptide thioamides to isoimide intermediates, which undergo site-selective intramolecular acyl transfer to serine/threonine side chains to generate the macrolactone.
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Awarded by Australian Research Council
This work was supported by the Australian Research Council (DP180101804 and DP150100692). The support of the Bio21 Institute MSP and MSPF facilities is acknowledged. S. S. acknowledges an Albert Shimmins Fund Award and aMRS from The University of Melbourne.