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Determination of the Relative Configurations in the Side Chains of the Antibiotics Hedamycin and Pluramycin A; Synthesis and NMR. Data of Suitable Model Compounds

✍ Scribed by Mario Ceroni; Urs Séquin

Publisher: John Wiley and Sons
Year: 1982
Tongue: German
Weight: 941 KB
Volume: 65
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19820650133

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✦ Synopsis

Abstract

Several diepoxyhexanoates and epoxyhexenoates were prepared by epoxidation of methyl 2‐methyl‐2,4‐hexadienoate or by Darzens condensation. Their ^1^ H‐ and ^13^C‐NMR. spectra were measured and assigned. Comparison of these data with the spectra of the antibiotics hedamycin (1) and pluramycin A (2) allowed the determi‐nation of the relative configurations in the side chains of these antibiotics. They were found to be (14__R__*,16__S__*,17__R__*,18__S__*) for hedamycin (1) and (14__R__*,16__S__*,17__Z__) for pluramycin A (2).

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