Stereoselective synthesis of original spirolactams displaying promising folded structures.

Abstract : Access to diastereoisomeric forms of original spirolactam frameworks and investigation of their folded potentials are depicted here. Taking advantage of a stereoselective ring-contraction reaction, the Transannular Rearrangement of Activated Lactams (TRAL), followed by two unprecedented tandem reactions, we describe here an efficient access to elegant spirocyclic scaffolds. After dimerization, NMR analyses, circular dichroism, SEM and molecular modelling indicated the existence of an attractive edifice able to fold and behave as a PPII helix, a common yet neglected peptidic secondary structure.
Document type :
Journal articles
Liste complète des métadonnées

Cited literature [42 references]  Display  Hide  Download

https://hal.archives-ouvertes.fr/hal-00871067
Contributor : Muriel Cadieu <>
Submitted on : Monday, December 16, 2013 - 9:05:37 AM
Last modification on : Thursday, December 20, 2018 - 11:18:54 AM
Document(s) archivé(s) le : Tuesday, March 18, 2014 - 12:20:16 PM

Files

Stereoselective-synthesis-acce...
Files produced by the author(s)

Identifiers

Citation

Guilhem Chaubet, Thibault Coursindel, Xavier Morelli, Stéphane Betzi, Philippe Roche, et al.. Stereoselective synthesis of original spirolactams displaying promising folded structures.. Organic and Biomolecular Chemistry, Royal Society of Chemistry, 2013, 11 (28), pp.4719-26. ⟨10.1039/c3ob40643a⟩. ⟨hal-00871067⟩

Share

Metrics

Record views

390

Files downloads

436