The absolute configuration of isochamigrene: new insights into the cyclisation mechanism of trichodiene synthase

Abstract

Isochamigrene, a side product of the trichodiene synthase, which is a key enzyme from the biosynthesis of the trichothecene mycotoxins from Fusarium spp., was enantioselectively synthesised and compared to the natural product from Fusarium sporotrichioides. As a result, its absolute configuration was assigned to (S)-isochamigrene. Implications for the recently extensively discussed cyclisation mechanism towards trichodiene and its side products are discussed.