51909-61-6Relevant academic research and scientific papers
Synthesis and comparative antibacterial activity of verdamicin C2 and C2a. A new oxidation of primary allylic azides in dihydro[2H]pyrans
Hanessian, Stephen,Szychowski, Janek,Pablo Maianti
supporting information; experimental part, p. 429 - 432 (2009/09/25)
(Chemical Equation Presented) A synthesis of verdamicin C2 and its congener C2a has been accomplished from sisomicin relying on a novel oxidative transformation of an allylic azide to the corresponding α,β- unsaturated aldehyde, and its stereocontrolled elaboration into the intended 5′ side chain of verdamicin C2 and C2a. In vitro antibacterial testing shows that both C6′ epimers in verdamicin C2 and C2a are equally active against a variety of bacterial strains. Oxidation of allylic primary azides, ethers, and esters of 2-substituted dihydro[2H]pyrans with SeO2 leads directly to the corresponding aldehydes.
Semisynthetic aminoglycoside antibacterials. 6. Synthesis of sisomicin, antibiotic G-52, and novel 6'-substituted analogues of sisomicin from aminoglycoside 66-40C
Davies,Mallams,Counelis,Loebenberg,Moss Jr.,Waitz
, p. 189 - 193 (2007/10/05)
The discovery of aminoglycoside 66-40C, a novel dimeric, unsaturated imine produced by Micromonospora inyoensis, afforded a versatile intermediate for the synthesis of a variety of sisomicin analogues modified at the 6' position. The conversion of 66-40C into sisomicin, antibiotic G-52, and a series of novel 6'-substituted analogues of sisomicin is described, and the biological activity of the products is discussed.
