Expanding the scope of the successive ring expansion strategy for macrocycle and medium-sized ring synthesis: unreactive and reactive lactams

Zhongzhen Yang; Marion Arnoux; Damien Hazelard; Owen R. Hughes; Joe Nabarro; Adrian C. Whitwood; Martin A. Fascione; Christopher D. Spicer; Philippe Compain; William P. Unsworth

doi:10.1039/D4OB00285G

Expanding the scope of the successive ring expansion strategy for macrocycle and medium-sized ring synthesis: unreactive and reactive lactams†

Zhongzhen Yang,

^ab Marion Arnoux,^c Damien Hazelard,

^c Owen R. Hughes,

^ad Joe Nabarro,^ad Adrian C. Whitwood,

^a Martin A. Fascione,

^ad Christopher D. Spicer,

^ad Philippe Compain

*^c and William P. Unsworth

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, University of York, Heslington, York, UK
E-mail: william.unsworth@york.ac.uk

^b Department of Pharmacy, West China Hospital, Sichuan University, Chengdu 610041, China

^c Laboratoire d'Innovation Moléculaire et Applications (LIMA), Univ. de Strasbourg, Univ. de Haute-Alsace, CNRS (UMR 7042), Equipe de Synthèse Organique et Molécules Bioactives (SYBIO), ECPM, 25 Rue Becquerel, 67000 Strasbourg, France
E-mail: philippe.compain@unistra.fr

^d York Biomedical Research Institute, University of York, Heslington, UK

Abstract

New methods are described that expand the scope of the Successive Ring Expansion (SuRE) with respect to synthetically challenging lactams. A protocol has been developed for use with ‘unreactive’ lactams, enabling SuRE reactions to be performed on subsrates that fail under previously established conditions. Ring expansion is also demonstarted on ‘reactive’ lactams derived from iminosugars for the first time. The new SuRE methods were used to prepare a diverse array of medium-sized and macrocyclic lactams and lactones, which were evaluted in an anti-bacterial assay against E. coli BW25113WT.

Organic & Biomolecular Chemistry

Expanding the scope of the successive ring expansion strategy for macrocycle and medium-sized ring synthesis: unreactive and reactive lactams†

Abstract

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Expanding the scope of the successive ring expansion strategy for macrocycle and medium-sized ring synthesis: unreactive and reactive lactams

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