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

Abstract

Owing to their unacceptable toxicity natural illudins are of limited interest as antitumor agents. In an attempt to exploit their cytotoxic potential several derivatives have been synthesized to obtain compounds with an improved therapeutic index. In this paper we describe some alkylation and oxidation reactions giving rise in some cases to less cytotoxic derivatives. Structures and relative stereochemistries have been determined on the basis of ¹H and ¹³C NMR evidence. All the compounds are less cytotoxic than illudin M and S but still very active.