Bicyclomycin, a new antibiotic. II. Structural elucidation and acyl derivatives.

The structure of bicyclomycin, a novel antibiotic, was largely elucidated by nuclear magnetic resonance spectroscopy and established finally as 8,10-diaza6-hydroxy-5-methylene-l-(2'-methyl-l/, 2/, 3/-trihydroxy-propyl)-2-oxabicyclo [4, 2, 2] decan-7, 9-dione by X-ray crystallographic diffraction analysis. A number of its acyl derivatives were prepared and studied biologically. The relationship between the structure of the acyl derivatives and the rate of urinary excretion was also examined.