Synthesis and free radical scavenging activity of a novel metabolite from the fungus Colletotrichum gloeosporioides

A novel metabolite (−)-1 was isolated as its peracetylated derivative, (−)-2-(3′,4′-diacetoxyphenyl)-3,4-diacetoxytetrahydrofuran (2), from a strain of the phytopathogenic fungus Colletotrichum gloeosporioides CECT 20122. The synthesis of (−)-1 was carried out by ring-closing metathesis of diene 6 and stereoselective dihydroxylation of a dihydrofuran derivative 7 as key steps. The tetraol (−)-1 showed free radical scavenging activity comparable to that of BHT, caffeic acid or protocatechuic acid.