Further studies on hydroxyperezone derivatives

Hydroxyperezone monoangelate (2c) was transformed into the mixture of α-(8) and β-perezols (9). Separation of these compounds permitted stereochemical assignments by NMR and ORD. The position of the angeloyl moiety in 2c was independently tested by its conversion to O-methylhydroxyperezone (1d) identified with a sample synthesised from perezone (1a). Several reactions distinguished the natural hydroxyperezone (2a) from the synthetic hydroxyperezone hydrate (3).