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Issue 28, 2013
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Stereoselective synthesis of original spirolactams displaying promising folded structures

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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.

Graphical abstract: Stereoselective synthesis of original spirolactams displaying promising folded structures

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Article information


Submitted
01 Apr 2013
Accepted
21 May 2013
First published
23 May 2013

Org. Biomol. Chem., 2013,11, 4719-4726
Article type
Paper

Stereoselective synthesis of original spirolactams displaying promising folded structures

G. Chaubet, T. Coursindel, X. Morelli, S. Betzi, P. Roche, Y. Guari, A. Lebrun, L. Toupet, Y. Collette, I. Parrot and J. Martinez, Org. Biomol. Chem., 2013, 11, 4719
DOI: 10.1039/C3OB40643A

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