Synthesis 2020; 52(20): 2970-2978
DOI: 10.1055/s-0040-1707886
psp
© Georg Thieme Verlag Stuttgart · New York

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
a  Université de Paris, CiTCoM, CNRS, 4 avenue de l’observatoire, 75006 Paris, France   Email: Joelle.perard@parisdescartes.fr
,
Wassila Drici
b  Université 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
a  Université de Paris, CiTCoM, CNRS, 4 avenue de l’observatoire, 75006 Paris, France   Email: Joelle.perard@parisdescartes.fr
,
Imane Lazouni
b  Université 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
a  Université de Paris, CiTCoM, CNRS, 4 avenue de l’observatoire, 75006 Paris, France   Email: Joelle.perard@parisdescartes.fr
,
a  Université de Paris, CiTCoM, CNRS, 4 avenue de l’observatoire, 75006 Paris, France   Email: Joelle.perard@parisdescartes.fr
› Author Affiliations
Financial support of this work by Université de Paris (grant to Sébastien Thueillon).
Further Information

Publication History

Received: 01 April 2020

Accepted after revision: 20 May 2020

Publication Date:
23 June 2020 (online)


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.

Supporting Information

 
  • References


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