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Vermiculin derivatives. Part 1: Synthesis of vermiculin derivatives
B Proksa1, D Uhrín, J Adamacová
1Department of Biochemical Technology, Faculty of Chemistry, Technical University, Modra, Slovakia.
Die Pharmazie
|October 1, 1993
Abstract:
Hydrogenation of the macrodiolide antibiotic vermiculin (1) over Adams catalyst afforded [8S, 16S]-8,16-bis(2'-oxopropyl)-1,9- dioxyacyclohexadeca-2,5,10,13-tetrone (2), [8S, 16S]-8,16-bis(2'-oxopropyl)-13-hydroxy-1,9-dioxacyclohexadeca- 2,5,10-trione (3), [8S,16S]-8,16-bis(2' oxopropyl)-1,9- dioxacyclohexadeca-2,5,10-trione (4) together with [7S]-4,9-dioxo-7-(4',9'-dioxodecanoyloxy)decanoic acid (5). Hydrogenation of diolide 1 over Pd/C gave tetrahydrovermiculin (2) only. The prepared compounds showed lower antibacterial and cytotoxic activities than vermiculin (1).