Abstract
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 language | English (US) |
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Pages (from-to) | 6476-6479 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 13 |
Issue number | 24 |
DOIs | |
State | Published - Dec 16 2011 |
Externally published | Yes |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry