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1 article(s) from Drouin, Myriam

Recent progress in the racemic and enantioselective synthesis of monofluoroalkene-based dipeptide isosteres

Myriam Drouin and
Jean-François Paquin

Beilstein J. Org. Chem. 2017, 13, 2637–2658, doi:10.3762/bjoc.13.262

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Graphical Abstract

Figure 1: Selected amide bond isosteres.

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Figure 2: Monofluoroalkene as an amide bond isostere.

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Scheme 1: Synthesis of Cbz-Gly-ψ[(Z)-CF=CH]-Gly using a HWE olefination by Sano and co-workers.

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Scheme 2: Synthesis of Phth-Gly-ψ[CF=CH]-Gly using the Julia–Kocienski olefination by Lequeux and co-workers.

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Scheme 3: Synthesis of Boc-Nva-ψ[(Z)-CF=CH]-Gly by Taguchi and co-workers.

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Figure 3: Mutant tripeptide containing two different peptide bond isosteres.

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Scheme 4: Chromium-mediated synthesis of Boc-Ser(PMB)-ψ[(Z)-CF=CH]-Gly-OMe by Konno and co-workers.

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Scheme 5: Synthesis of Cbz-Gly-ψ[(E)-CF=C]-Pro by Sano and co-workers.

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Scheme 6: Synthesis of Cbz-Gly-ψ[(Z)-CF=C]-Pro by Sano and co-workers.

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Scheme 7: Stereoselective synthesis of Fmoc-Gly-ψ[(Z)-CF=CH]-Phe by Pannecoucke and co-workers.

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Scheme 8: Ring-closure metathesis to prepare Gly-ψ[(E)-CF=CH]-Phg by Couve-Bonnaire and co-workers.

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Scheme 9: Stereoselective synthesis of Fmoc-Gly-ψ[(Z)-CF=CH]-Phe by Dory and co-workers.

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Scheme 10: Diastereoselective addition of Grignard reagents to sulfinylamines derived from α-fluoroenals by Pa...

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Scheme 11: NHC-mediated synthesis of monofluoroalkenes by Otaka and co-workers.

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Scheme 12: Stereoselective synthesis of Boc-Tyr-ψ[(Z)-CF=CH]-Gly by Altman and co-workers.

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Scheme 13: Synthesis of the tripeptide Boc-Asp(OBn)-Pro-ψ[(Z)-CF=CH)-Val-CH₂OH by Miller and co-workers.

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Scheme 14: Copper-catalyzed synthesis of monofluoralkenes by Taguchi and co-workers.

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Scheme 15: One-pot intramolecular redox reaction to access amide-type isosteres by Otaka and co-workers.

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Scheme 16: Copper-mediated reduction, transmetalation and asymmetric alkylation by Fujii and co-workers.

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Scheme 17: Synthesis of (E)-monofluoroalkene-based dipeptide isostere by Fujii and co-workers.

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Scheme 18: Diastereoselective synthesis of MeOCO-Val-ψ[(Z)-CF=C]-Pro isostere by Chang and co-workers.

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Scheme 19: Asymmetric synthesis of Fmoc-Ala-ψ[(Z)-CF=C]-Pro by Pannecoucke and co-workers.

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Scheme 20: Synthesis of Fmoc-Val-ψ[(E)-CF=C]-Pro by Pannecoucke and co-workers.

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Figure 4: BMS-790052 and its fluorinated analogue.

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Figure 5: Bioactivities of pentapeptide analogues based on the relative maximum agonistic activity at 10 nM o...

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Figure 6: Structures and affinities of the Leu-enkephalin and its fluorinated analogue. The affinity towards ...

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Figure 7: Activation of the opioid receptor DOPr by Leu-enkephaline and a fluorinated analogue.

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Review

Published 12 Dec 2017

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