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Total synthesis of (±)-fumimycin and analogues for biological evaluation as peptide deformylase inhibitors.

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Mercier,  E.
Research Group of Ribosome Dynamics, MPI for biophysical chemistry, Max Planck Society;

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Wintermeyer,  W.
Research Group of Ribosome Dynamics, MPI for biophysical chemistry, Max Planck Society;

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Citation

Zaghouania, M., Bögeholz, L. A. K., Mercier, E., Wintermeyer, W., & Roche, S. P. (2019). Total synthesis of (±)-fumimycin and analogues for biological evaluation as peptide deformylase inhibitors. Tetrahedron, 75(24), 3216-3230. doi:10.1016/j.tet.2019.03.037.


Cite as: http://hdl.handle.net/21.11116/0000-0003-D0E4-0
Abstract
A concise 7-step total synthesis of (±)-fumimycin in 11.6% overall yield is reported. An acid-catalyzed intramolecular aza-Friedel–Crafts cyclization was developed to construct the benzofuranone skeleton of the natural product bearing an α,α-disubstituted amino acid moiety in a single step. Regioselective chlorination followed by a Suzuki–Miyaura cross-coupling rapidly enabled the preparation of a library of analogues which were evaluated against peptide deformylase for antibacterial activity.