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Napyradiomycins A2 and B4, new members of the napyradiomycins, have been isolated from the culture broth of Chainia rubra MG802-AF1. The structure of napyradiomycin A2 was elucidated as 16-hydroxy-17-methylenenapyradiomycin A1 by NMR studies. The absolute structure of napyradiomycin B4 was determined as 13-hydroxy-13-methylnapyradiomycin B1 by X-ray crystallography and therefore the configuration of C(4a) in other napyradiomycins is assumed as the R configuration. The geometrical isomerism of napyradiomycin C1 was estimated as 12E and 16E by nuclear Overhauser effect experiments.

New antibiotic napyradiomycins A2 and B4 and stereochemistry of napyradiomycins.