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Straightforward and Diastereoselective Synthesis of Tetrafunctionalized Thiol Synthons for the Design of Metallopeptidase Inhibitors

Christelle David 1 Laurent Bischoff 1, * Bernard Roques 1 Marie-Claude Fournie-Zaluski 1
* Corresponding author
1 Pharmacochimie moléculaire et structurale
Abstract : Tetrafunctionalized thiol-containing synthons with different side-chains have been prepared with good yields by a straightforward diastereoselective and general methodology. The key step of the synthesis consisted of a tandem reduction and Wittig–Horner reaction, which conserved the stereochemistry of the starting material. The method was generalized to different side-chains, allowing synthons for designing inhibitors of various classes of zinc metallopeptidases to be easily obtained.
Keywords : amino acids and derivatives thiol enzyme inhibitors Wittig–Horner reaction
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02385509
Contributor : Laurent Bischoff <>
Submitted on : Thursday, November 28, 2019 - 6:49:25 PM
Last modification on : Tuesday, September 22, 2020 - 3:38:39 AM

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COMUE-NORMANDIE | IFR71 | ENSCP | UNIV-PARIS5 | PARISTECH | USPC | CNRS | INSERM | UNILEHAVRE | UNIV-PARIS | PSL

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Christelle David, Laurent Bischoff, Bernard Roques, Marie-Claude Fournie-Zaluski. Straightforward and Diastereoselective Synthesis of Tetrafunctionalized Thiol Synthons for the Design of Metallopeptidase Inhibitors. Tetrahedron, Elsevier, 2000, 56 (2), pp.209-215. ⟨10.1016/S0040-4020(99)00922-9⟩. ⟨hal-02385509⟩

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