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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Expanding the scope of the successive ring expansion strategy for macrocycle and medium-sized ring synthesis:
Zhongzhen Yang1,2, Marion Arnoux3, Damien Hazelard3
1Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK. william.unsworth@york.ac.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.
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