THE STRUCTURE OF ACETOMYCIN SPECTROSCOPIC CHARACTERIZATION AND X-RAY ANALYSIS OF A BROMO DERIVATIVE

HERMANN UHR; AXEL ZEECK; WILLIAM CLEGG; ERNST EGERT; HERMANN FUHRER; HEINRICH H. PETER

doi:10.7164/antibiotics.38.1684

The Journal of Antibiotics

Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820

THE STRUCTURE OF ACETOMYCIN

SPECTROSCOPIC CHARACTERIZATION AND X-RAY ANALYSIS OF A BROMO DERIVATIVE

HERMANN UHR, AXEL ZEECK, WILLIAM CLEGG, ERNST EGERT, HERMANN FUHRER, HEINRICH H. PETER

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JOURNAL FREE ACCESS

1985 Volume 38 Issue 12 Pages 1684-1690

DOI https://doi.org/10.7164/antibiotics.38.1684

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Abstract

Acetomycin (1a), known since 1958, has been further characterized by NMR and CD spectra. The β-acetyl side chain of 1a is reduced selectively by sodium cyanoborohydride yielding the diastereomeric alcohols 2a and 3a, which were esterified to the crystalline bromoacetates 2c and 3c. The structure and absolute configuration of 3c was determined by X-ray analysis. From these data the absolute configuration of 1a followed as 3S, 4S, 5R.

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