Chemistry of the mycalamides, antiviral and antitumour compounds from a marine sponge. Part 5. Acid-catalysed hydrolysis and acetal exchange, double bond additions and oxidation reactions

Abstract

The acid-catalysed degradations of the potent antitumour and antiviral sponge metabolite mycalamide A and a triacetyl derivative have been examined. Acetal exchange reactions, catalytic hydrogenation, epoxidation and oxidation reactions have also been performed on mycalamides A and B. The major products derived from these reactions were characterised and tested for in vitro P388 anti-leukaemia activity and structure–activity relationships were deduced from these results.