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

Abstract

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 ).