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Pando, O., Stark, S., Denkert, A., Porzel, A., Preusentanz, R. & Wessjohann, L. The multiple multicomponent approach to natural product mimics: Tubugis N-substituted anticancer peptides with picomolor activity J. Am. Chem. Soc 133, 7692-7695, (2011) DOI: 10.1021/ja2022027

The synthesis of a new generation of highly cytotoxic tubulysin analogues (i.e., tubugis) is described. In the key step, the rare, unstable, and synthetically difficult to introduce tertiary amide–N,O-acetal moiety required for high potency in natural tubulysins is replaced by a dipeptoid element formed in an Ugi four-component reaction. Two of the four components required are themselves produced by other multicomponent reactions (MCRs). Thus, the tubugis represent the first examples of the synthesis of natural-product-inspired compounds using three intertwined isonitrile MCRs.

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