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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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Hybrid aminoglycoside antibiotics via Tsuji palladium-catalyzed allylic deoxygenation.

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.[1]

References

  1. Hybrid aminoglycoside antibiotics via Tsuji palladium-catalyzed allylic deoxygenation. Hanessian, S., Maianti, J.P., Matias, R.D., Feeney, L.A., Armstrong, E.S. Org. Lett. (2011) [Pubmed]
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