Abstract
Macrolide antibiotics of the polyene antifimgal subgroup undergo aerial autoxidation in methanol solution by a radical addition process which can be inhibited by antioxidants. The related pentaenes of the filipin complex, which has the main component (I), and lagosin (II) yield as the major primary products the corresponding tetraene epoxides (III) and (IV), which are probably mixtures of diastereoisomers. The structures of the products were established by spectroscopy and chemical degradation. Extended autoxidation leads to higher oxidation products and ultimately to polymeric materials.
