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The discovery of the extremely active iron catalyst enables aerobic enzyme\u2010mimetic oxidation to be performed in a flask. This method was applicable to the oxidative dimerization of a wide range of tryptophan derivatives, including various dipeptides and oligopeptides, with remarkable functional\u2010group tolerance without the protection of the amino acid residues. Furthermore, oxidative dimerization of tryptophan derivatives bearing dioxopiperazine units enabled the convergent total synthesis of five natural pyrroloindole compounds and unnatural congeners. 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For details see the Supporting Information."},{"key":"e_1_2_7_63_1","unstructured":"TheC2-symmetrical product possessing theR Rconfiguration at the positions linking the two units was obtained as the major isomer which was opposite to theS Sconfiguration of the products of reactions using the tryptophan ester and peptides having a tryptophan residue at the N-terminus."},{"key":"e_1_2_7_64_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201503417"},{"key":"e_1_2_7_65_1","doi-asserted-by":"publisher","DOI":"10.1038\/284033a0"},{"key":"e_1_2_7_66_1","doi-asserted-by":"publisher","DOI":"10.1038\/386499a0"},{"key":"e_1_2_7_67_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.74.3.1282"},{"key":"e_1_2_7_68_1","unstructured":"The structure of the dimerized product was tentatively assigned based on LC\u2013MS. The major three or four peaks detected by LC were determined to show the molecular ion peak of the dimer in MS. 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