Hybrid aminoglycoside antibiotics via tsuji palladium-catalyzed allylic deoxygenation

Stephen Hanessian, Juan Pablo Maianti, Rowena D. Matias, Lee Ann Feeney, Eliana S. Armstrong

Research output: Contribution to journalArticlepeer-review

20 Scopus citations


Biosynthetically inspired manipulation of the antibiotic paromomycin led, in six high-yielding steps, to a ring A harboring an R,β-unsaturated 6′- aldehyde and an allylic 3′-methylcarbonate group. Tsuji deoxygenation in the presence of 5 mol % Pd 2(dba) 3 and Bu 3P 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.

Original languageEnglish (US)
Pages (from-to)6476-6479
Number of pages4
JournalOrganic Letters
Issue number24
StatePublished - Dec 16 2011
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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