Synthesis of Inducamides A and B

The inducamides are a family of chlorinated alkaloids featuring an amide arising from union of an l-tryptophan to a rare chlorosalicylic acid unit, the production of which is linked to a chemically induced mutation in the RNA polymerase of Streptomyces sp. (SNC-109-M3). The synthesis of inducamides A and B has been accomplished by the coupling of 6-hydroxy-3-chloro-2-methylbenzoic acid with l-6-chlorotryptophan and l-tryptophan, respectively, followed by ester hydrolysis. The spectroscopic data and optical rotation for each synthetic sample confirm the structures of these silent secondary metabolites and their biosynthesis from l-tryptophan.