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

Zaghouania, M., Bögeholz, L. A., 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.

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Item Permalink: http://hdl.handle.net/21.11116/0000-0003-D0E4-0 Version Permalink: http://hdl.handle.net/21.11116/0000-0003-D0E6-E
Genre: Journal Article

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Zaghouania, M., Author
Bögeholz, Lena A.K., Author
Mercier, E.1, Author              
Wintermeyer, W.2, Author              
Roche, S. P., Author
Affiliations:
1Department of Physical Biochemistry, MPI for Biophysical Chemistry, Max Planck Society, ou_578598              
2Research Group of Ribosome Dynamics, MPI for biophysical chemistry, Max Planck Society, ou_578599              

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 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.

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Language(s): eng - English
 Dates: 2019-03-272019-06-14
 Publication Status: Published in print
 Pages: -
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 Table of Contents: -
 Rev. Method: Peer
 Identifiers: DOI: 10.1016/j.tet.2019.03.037
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Title: Tetrahedron
Source Genre: Journal
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Pages: - Volume / Issue: 75 (24) Sequence Number: - Start / End Page: 3216 - 3230 Identifier: -