Trichodermin, a New Sesquiterpene Antibiotic.

Abstract

The antifungal antibiotic Trichodermin, C17H24O4, which is the acetate of a sesquiterpene alcohol trichodermoL C15H22O3, has been correlated with trichothecin. The structure based upon the previously proposed trichothecin structure (Ia) was incompatible with certain reactions, and trichodermol-p-bromobenzoate was therefore subjected to an X-ray crystallographic analysis which revealed that trichodermol represents a new sesquiterpene type (IIIc). Based upon the Trichodermin structure a revised formula of trichothecin (IIId) is proposed. The relationship of Trichodermin (IIIb) to the verrucarines and roridines is discussed. Some unusual rearrangements of the trichodermol ring system are described, and its biogenesis shortly discussed.