The first synthesis of the indole phytoalexin cyclobrassinon and some of its analogues, possessing a thiazino [6, 5-b] indol-4-one tricyclic ring system was performed starting from 1- substitued 2-chloroindole-3-carboxaldehydes. The route employed the intramolecular Et3N- mediated or photochemical nucleophilic substitution of a chlorine atom in the 2-position of the indole ring with a sulfur atom as a key step. Examination of biological activity against ...