Synlett 2022; 33(04): 396-400
DOI: 10.1055/s-0040-1719876
letter

Skeletal Analogues of UCS1025A and B by Cyclization of Maleimides: Synthesis and Biological Activity

Lewis T. Ibbotson
a   The Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK
,
Kirsten E. Christensen
a   The Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK
,
Miroslav Genov
b   Oxford Antibiotic Group, The Oxford Science Park, Magdalen Centre, Oxford OX4 4GA, UK
,
Alexander Pretsch
b   Oxford Antibiotic Group, The Oxford Science Park, Magdalen Centre, Oxford OX4 4GA, UK
,
Dagmar Pretsch
b   Oxford Antibiotic Group, The Oxford Science Park, Magdalen Centre, Oxford OX4 4GA, UK
,
Mark G. Moloney
a   The Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK
c   Oxford Suzhou Centre for Advanced Research, Building A, 388 Ruo Shui Road, Suzhou Industrial Park, Jiangsu, 215123, P. R. of China
› Author Affiliations


Abstract

Application of a direct ring-closing approach which exploits an intramolecular aldol reaction with a ketene silyl acetal onto a remote imide function leading to the core skeleton of UCS1025A and B effectively provides access to small library of substituted analogues; of interest is their complete lack of antibacterial activity against MRSA (Gram+) and E. coli (Gram–) bacterial strains.

Supporting Information



Publication History

Received: 18 October 2021

Accepted after revision: 10 December 2021

Article published online:
27 January 2022

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