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)|
|Number of pages||4|
|State||Published - Dec 16 2011|
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry