Moenomycin analogues with modified lipid side chains from indium-mediated Barbier-type reactions

From moenomycin A both the chromophore part and the lipid side chain were degraded by ozonolysis to give an analogue with a glycolaldehyde unit in 2-position of the glyceric acid moiety. The aldehyde was converted to a number of homoallylic alcohols by indium-mediated Barbier-type reactions with allylic and benzylic halides. With exception of the phytyl bromide-derived reaction product all compounds were antibiotically inactive.