Total Synthesis of the Toxin Oosponol and of Structural Analogues and Investigation of Their Antibiotic Activities

Abstract

The toxic metabolite of the basidiomycete Gloeophyllum abietinum, oosponol (6b), and the structural analogues (Figure 1) were synthesised in order to investigate which partial structures of the molecules are responsible for their biological activities. Different organisms were employed to test the antibiotic activities of the analogues. From the results obtained with the synthetic analogues of oosponol (6b), it became evident that the toxicity of this fungal metabolite can be attributed to a vinylogous acid anhydride structure, which in nature is produced by dehydrogenation of the nontoxic precursor oospoglycol (7).