Hybrid aminoglycoside antibiotics via Tsuji palladium-catalyzed allylic deoxygenation |
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Authors: | Hanessian Stephen Maianti Juan Pablo Matias Rowena D Feeney Lee Ann Armstrong Eliana S |
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Institution: | Department of Chemistry, Université de Montréal, C. P. 6128, Succ. Centre-Ville, Montréal, QC, Canada, H3C 3J7. stephen.hanessian@umontreal.ca |
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Abstract: | Biosynthetically inspired manipulation of the antibiotic paromomycin led, in six high-yielding steps, to a ring A harboring an α,β-unsaturated 6'-aldehyde and an allylic 3'-methylcarbonate group. Tsuji deoxygenation in the presence of 5 mol % Pd(2)(dba)(3) and Bu(3)P granted access to a novel series of 3',4'-dideoxy-4',5'-dehydro ring A hybrids. The neomycin-sisomicin hybrid exhibited superior in vitro antibacterial activity to the parent compound neomycin. |
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