The total structure of the novel antibiotic mocimycin (MYC 8003)

✍ Scribed by C. Vost; P.E.J. Verwiel

• Publisher: Elsevier Science
• Year: 1973
• Tongue: French
• Weight: 195 KB
• Volume: 14
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)87655-3

✦ Synopsis

Recently we reported on the structures 1 and g of two degradation products of mocimycin (1).

Further work has now led to the elucidation of the structure of the complete mocimycin molecule 5.

The previous experiments indicated that fragment g might be an artefact and that methylation of a hydroxylgroup might have taken place under the applied conditions (acidic methanolysis).

This was confirmed by treating mocimycin with acetic acid at room temperature for several day! An a,;olar diene, z, was obtained, together with a polar compound s, which was acetylated with a mixture of acetic anhydride and pyridine to give s. The W spectrum of 2 showed the presence of fragment 1. The structure of e was derived from its 220 MHz proton NMR spectrum; for data see diagram.