The first synthesis of 7-prenylisatin

The first synthesis of 7-prenylisatin, an isatin-type antibiotic with prominent activity against Bacillus subtilis, has been accomplished in 16% overall yield from 2-methylbut-3-en-2-ol and aniline via a five-step procedure. The protocol includes the aromatic aza-Claisen rearrangement and the Sandmeyer isonitrosoacetanilide isatin synthesis as key steps.