1,3-Dipolar cycloaddition of stabilised and non-stabilised azomethine ylides derived from uracil polyoxin C (UPoC): access to nikkomycin analogues |
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| Authors: | H.Ali Dondas Colin W.G Fishwick Colin Kilner |
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| Affiliation: | a Molecular Innovation, Diversity and Automated Synthesis (MIDAS) Centre, Department of Chemistry, The University of Leeds, Leeds LS2 9JT, UK
b Department of Chemistry, Faculty of Pharmacy, Mersin University, Mersin, Turkey |
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| Abstract: | Cascade thermal and decarboxylative cycloaddition reactions of uracil polyoxin C (UPoC) with mono- and di-carbonyl compounds in the presence of a dipolarophile leads, via stabilised and non-stabilised azomethine ylides respectively, to a series of polyoxin cycloadducts related to Nikkomycin B in good to excellent yields and high diastereoselectivity. |
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| Keywords: | Uracil polyoxin C Nikkomycin Azomethine ylide 1,3-Dipolar cycloaddition Chitin synthetase inhibitors Decarboxylative cycloaddition Semi-empirical Calculations |
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