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Synthesis of Camalexin and Related Analogues

2018; Wiley; Volume: 55; Issue: 7 Linguagem: Inglês

10.1002/jhet.3192

1943-5193

Yordan Stremski, Stela Statkova‐Abeghe, Plamen Angelov, Iliyan Ivanov,

Alkaloids: synthesis and pharmacology

Camalexin is synthesized on a gram scale by coupling of thiazole and indole in an amidoalkylation–oxidation sequence. Several high‐yielding implementations of this two‐step approach are demonstrated with variation of either the intermediate acyliminium reagent or the oxidation conditions. Benzo‐analogues and aza‐analogues of the natural product are also obtained by this method. As a side result, a new formylation of indole is demonstrated.