Hydrogenation of the macrodiolide antibiotic vermiculin (1) over Adams
catalyst afforded [8S, xopropyl)-1,9-dioxacyclohexadeca-2,5,10,13-tet
rone l)-13-hydroxy-1,9-dioxacyclohexadeca-2,5,10-trione (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 compound
s showed lower antibacterial and cytotoxic activities than vermiculin
(1).