N-Acyliminium Ion Chemistry: Improving the Access to Unsaturated γ-Lactams and Their N-α-Methoxylated Derivatives: Application to an Expeditive Synthesis of (±)-Crispine A

Florence Souquet; Wassila Drici; Sandra Abi Fayssal; Imane Lazouni; Sébastien Thueillon; Joëlle Pérard-Viret

doi:10.1055/s-0040-1707886

Synthesis, Table of Contents

Synthesis 2020; 52(20): 2970-2978
DOI: 10.1055/s-0040-1707886

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N-Acyliminium Ion Chemistry: Improving the Access to Unsaturated γ-Lactams and Their N-α-Methoxylated Derivatives: Application to an Expeditive Synthesis of (±)-Crispine A

Florence Souquet

^aUniversité de Paris, CiTCoM, CNRS, 4 avenue de l’observatoire, 75006 Paris, France Email: Joelle.perard@parisdescartes.fr

,

Wassila Drici

^bUniversité de Tlemcen, Laboratoire de chimie organique, substances naturelles et analyses (COSNA), département de chimie, faculté des sciences, 22 Rue Abi Ayed Abdelkrim Fg Pasteur B.P 119 13000, Tlemcen, Algérie

,

Sandra Abi Fayssal

^aUniversité de Paris, CiTCoM, CNRS, 4 avenue de l’observatoire, 75006 Paris, France Email: Joelle.perard@parisdescartes.fr

,

Imane Lazouni

^bUniversité de Tlemcen, Laboratoire de chimie organique, substances naturelles et analyses (COSNA), département de chimie, faculté des sciences, 22 Rue Abi Ayed Abdelkrim Fg Pasteur B.P 119 13000, Tlemcen, Algérie

,

Sébastien Thueillon

^aUniversité de Paris, CiTCoM, CNRS, 4 avenue de l’observatoire, 75006 Paris, France Email: Joelle.perard@parisdescartes.fr

,

Joëlle Pérard-Viret ∗

^aUniversité de Paris, CiTCoM, CNRS, 4 avenue de l’observatoire, 75006 Paris, France Email: Joelle.perard@parisdescartes.fr

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Abstract

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Dedicated to Dr. Jacques Royer

Abstract

An improved synthesis of unsaturated γ-lactams by condensation of various primary amines with 2,5-dimethoxy-2,5-dihydrofuran is described. A modified mechanism for this reaction is suggested. Synthesis of their N-α-methoxylated derivatives, as N-acyliminium ion precursors, is also reported. Finally, a short synthesis of (±)-crispine A is presented as an illustrative application.

Key words

unsaturated γ-lactams - aza-heterocycles - N-acyliminium - 5-methoxypyrrolidin-2-one - crispine A

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References

References

Present address:

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Supplementary Material

Supporting Information