ol0c00202_si_001.pdf (3.36 MB)
Total Synthesis of Micrococcin P1 through Scalable Thiazole Forming Reactions of Cysteine Derivatives and Nitriles
journal contribution
posted on 2020-03-05, 14:04 authored by Mitchell
P. Christy, Trevor Johnson, Clare D. McNerlin, John Woodard, Andrew T. Nelson, Bryant Lim, Tiffany L. Hamilton, Kaitlyn M. Freiberg, Dionicio SiegelThiopeptides
are a class of natural products with untapped therapeutic
potential. To expand the methods available for the scaled production
of these antibiotics, we report the laboratory synthesis of micrococcin
P1 showcasing thiazole forming reactions of cysteine derivatives and
nitriles followed by oxidation. In most instances, this thiazole forming
sequence does not require chromatography and proved scalable. Using
this approach, 199 mg of micrococcin P1 was generated in a single
synthetic sequence.