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2 article(s) from Retailleau, Pascal

Synthesis of extended fluorinated tripeptides based on the tetrahydropyridazine scaffold

Thierry Milcent,
Pascal Retailleau,
Benoit Crousse and
Sandrine Ongeri

Beilstein J. Org. Chem. 2024, 20, 3174–3181, doi:10.3762/bjoc.20.262

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Figure 1: Examples of bioactive tetrahydropyridazine derivatives.

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Figure 2: Linear and cyclic peptides incorporating the dehydropiperazic acid moiety.

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Figure 3: Piperazic acid and analogues and target trifluoro/difluoromethylated tetrahydropyridazine acids.

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Scheme 1: Reported syntheses of tetrahydropyridazine ester derivatives.

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Figure 4: Synthetic strategy to obtain fluorinated tetrahydropyridazines from difluoro- or trifluoromethylate...

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Scheme 2: Synthesis of fluorinated hydrazones 3a–f.

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Scheme 3: Allylation of fluorinated hydrazones 3a–f to obtain 5a–f.

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Scheme 4: Oxidation of hydrazines 5a–f to obtain hydrazones 6a–f.

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Scheme 5: Intramolecular cyclization of compounds 6a–f to obtain tetrahydropyridazines 7a–f.

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Scheme 6: Preparation of tripeptides 8e, 8e’, 8f, and 8f’. Yields refer to the yield over 2 steps.

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Figure 5: X-ray diffraction of compound 8f.

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Published 04 Dec 2024

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A mechanochemical approach to access the proline–proline diketopiperazine framework

Nicolas Pétry,
Hafid Benakki,
Eric Clot,
Pascal Retailleau,
Farhate Guenoun,
Fatima Asserar,
Chakib Sekkat,
Thomas-Xavier Métro,
Jean Martinez and
Frédéric Lamaty

Beilstein J. Org. Chem. 2017, 13, 2169–2178, doi:10.3762/bjoc.13.217

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Scheme 1: Retrosynthesis of the Pro–Pro DKP framework.

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Scheme 2: Coupling with N-hydroxysuccinimide-activated amino acids.

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Scheme 3: Synthesis of Pro–Pro DKP.

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Scheme 4: Synthesis of substituted Pro–Pro DKP 15a.

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Scheme 5: Potential isomers yielded by cyclization of 16.

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Figure 1: Optimized geometries for the two conformers presenting interactions with either C_a (16a) or C_b (16b...

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Figure 2: Optimized geometries of the extrema located along the pathway for formation of 15a with explicit pa...

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Figure 3: Optimized geometries of the extrema located along the pathway for formation of 15b with explicit pa...

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Figure 4: Optimized geometries for the transition states associated to alternate position of the methanol mol...

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Scheme 6: Synthesis of diketopiperazine 19.

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Published 19 Oct 2017

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