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The structure of the antibiotic hedamycon. IV. Relative configurations in the diepoxide side chain

✍ Scribed by Mario Ceroni; Urs Séquin

Book ID
104246499
Publisher
Elsevier Science
Year
1979
Tongue
French
Weight
206 KB
Volume
20
Category
Article
ISSN
0040-4039

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✦ Synopsis

The relative configurations in the diepoxide side chain of the antibiotic hedamycin have been shown to be rel-(14R,16S,17R,18S). The structure of the antibiotic hedamycin (1) has recently been elucidated in our laboratory. 2-4) However, the relative configurations in the unique diepoxide side chain at C(2) could not yet be determined. We now wish to present evidence in support of the configurations shown in formula 1. *1 Several epoxidized methyl 2methyl-2,4_hexadienoates were synthesized as model compounds for spectral comparisons. The esters 2, 2, and 4 were obtained by direct epoxidation of the parent diene 8 with m-chloroperbenzoic acid (MCPBA). After a short reaction period, 4 could be isolated; prolonged treatment with 1, hedamycin 2 "0_cis" 3 "0-trans" *) All compounds shown in the schemes are racemic, except 1. Carbon chemical shifts are given in ppm downfield from internal TMS.

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Determination of the Relative Configurat
Determination of the Relative Configurations in the Side Chains of the Antibiotics Hedamycin and Pluramycin A; Synthesis and NMR. Data of Suitable Model Compounds
✍ Mario Ceroni; Urs Séquin 📂 Article 📅 1982 🏛 John Wiley and Sons 🌐 German ⚖ 941 KB

## 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**) a