Chemistry of the mycalamides, antiviral and antitumour compounds from a marine sponge. Part 4. Reactions of mycalamide A and alkyl derivatives with basic nucleophiles

The chemistry of the potent antitumour and antiviral marine sponge metabolite, mycalamide A, and some of its alkyl derivatives, was examined by treatment with alkoxide, hydroxide and oxide bases in various solvents and with azide and hydride in dimethyl sulfoxide. The major rearrangement and cleavage products resulting from these reactions were characterised and tested for in vitro P388 anti-leukaemic activity.