Ring Expansion of Thiolactams via Imide Intermediates: An Amino Acid Insertion Strategy
Jing Shang, Varsha J Thombare, Carlie L Charron, Uta Wille, Craig A Hutton
Chemistry - A European Journal | WILEY-V C H VERLAG GMBH | Published : 2020
The AgI -promoted reaction of thiolactams with N-Boc amino acids yields an N-(α-aminoacyl) lactam that can rearrange through an acyl transfer process. Boc-deprotection results in convergence to the ring-expanded adduct, thereby facilitating an overall insertion of an amino acid into the thioamide bond to generate medium-sized heterocycles. Application to the site-specific insertion of amino acids into cyclic peptides is demonstrated.
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Awarded by Australian Research Council
This work was supported by the Australian Research Council (DP180101804 and DP150100692) and the High Performance Computing Facilities of The University of Melbourne. We acknowledge the support of the Bio21 Molecular Science and Biotechnology Institute MSP and Peptide Technologies facilities. V.T. acknowledges the award of a Norma Hilda Schuster Scholarship.