Secondary mould metabolites. Part 59. Sesquiterpene illudanes: semi-synthesis of new illudins, structures and biological activity

Owing to their unacceptable toxicity natural illudins are of limited intere st as antitumor agents. In an attempt to exploit their cytotoxic potential several derivatives have been synthesized to obtain compounds with an impro ved therapeutic index. In this paper we describe some alkylation and oxidat ion reactions giving rise in some cases to less cytotoxic derivatives. Stru ctures and relative stereochemistries have been determined on the basis of H-1 and C-13 NMR evidence. All the compounds are less cytotoxic than illudi n M and S but still very active.