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

Chemistry

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Number of pages	7
Journal	Organic & biomolecular chemistry
Early online date	25 Mar 2024
DOIs	https://doi.org/10.1039/d4ob00285g
Publication status	E-pub ahead of print - 25 Mar 2024

Access to Document

10.1039/d4ob00285gLicence: CC BY-NC

d4ob00285g(3)Final published version, 1.85 MBLicence: CC BY-NC

Cite this

Yang, Z., Arnoux, M., Hazelard, D., Hughes, O. R., Nabarro, J., Whitwood, A. C., Fascione, M. A., Spicer, C. D., Compain, P., & Unsworth, W. P. (2024). Expanding the scope of the successive ring expansion strategy for macrocycle and medium-sized ring synthesis: unreactive and reactive lactams. Organic & biomolecular chemistry. Advance online publication. https://doi.org/10.1039/d4ob00285g

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AU - Hughes, Owen R

AU - Nabarro, Joe

AU - Whitwood, Adrian C

AU - Fascione, Martin A

AU - Spicer, Christopher D

AU - Compain, Philippe

AU - Unsworth, William P

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