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Herein, we report a new asymmetric synthetic route to cytotrienin A, employing an unexplored approach involving the late\u2010stage installation of a C11 side chain onto the macrolactam core. In this strategy, we utilized the redox properties of hydroquinone and installed a side chain on the sterically hindered C11 hydroxy group by the traceless Staudinger reaction. This study also demonstrated that the boron\u2010Wittig\/iterative Suzuki\u2013Miyaura cross\u2010coupling sequence was effective for the concise and selective construction of the (<jats:italic>E<\/jats:italic>,<jats:italic>E<\/jats:italic>,<jats:italic>E<\/jats:italic>)\u2010conjugated triene moiety. The developed route opens new opportunities for the structure\u2013activity relationship studies of the side chains of these ansamycin antibiotics and the preparation of other synthetic analogs and chemical probes for further biological studies.<\/jats:p>","DOI":"10.1002\/anie.202303140","type":"journal-article","created":{"date-parts":[[2023,5,22]],"date-time":"2023-05-22T11:48:45Z","timestamp":1684756125000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Asymmetric Total Synthesis of Cytotrienin A: Late\u2010Stage Installation of C11 Side Chain onto the Macrolactam Scaffold"],"prefix":"10.1002","volume":"62","author":[{"given":"Yuki","family":"Tateishi","sequence":"first","affiliation":[{"name":"Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences Tohoku University  6-3 Aoba, Aramaki, Aoba-ku Sendai 980-8578 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ryo","family":"Sato","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences Tohoku University  6-3 Aoba, Aramaki, Aoba-ku Sendai 980-8578 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Shingo","family":"Komatsu","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences Tohoku University  6-3 Aoba, Aramaki, Aoba-ku Sendai 980-8578 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Masatsugu","family":"Noguchi","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences Tohoku University  6-3 Aoba, Aramaki, Aoba-ku Sendai 980-8578 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9207-4423","authenticated-orcid":false,"given":"Shota","family":"Nagasawa","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences Tohoku University  6-3 Aoba, Aramaki, Aoba-ku Sendai 980-8578 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3852-8607","authenticated-orcid":false,"given":"Yusuke","family":"Sasano","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences Tohoku University  6-3 Aoba, Aramaki, Aoba-ku Sendai 980-8578 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4382-3715","authenticated-orcid":false,"given":"Naoki","family":"Kanoh","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences Tohoku University  6-3 Aoba, Aramaki, Aoba-ku Sendai 980-8578 Japan"},{"name":"Current address: School of Pharmacy and Pharmaceutical Sciences, and Institute of Medicinal Chemistry Hoshi University  2-4-41, Ebara, Shinagawa-ku Tokyo 142-8501 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0679-939X","authenticated-orcid":false,"given":"Yoshiharu","family":"Iwabuchi","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences Tohoku University  6-3 Aoba, Aramaki, Aoba-ku Sendai 980-8578 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2023,6,12]]},"reference":[{"key":"e_1_2_3_1_1","unstructured":"\u00a0"},{"key":"e_1_2_3_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.crci.2008.07.003"},{"key":"e_1_2_3_3_2","first-page":"51","volume-title":"Studies in Natural Products Chemistry","author":"Funayama S.","year":"2000"},{"key":"e_1_2_3_4_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6RA19036G"},{"key":"e_1_2_3_5_1","unstructured":"Trienomycins;"},{"key":"e_1_2_3_6_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.38.699"},{"key":"e_1_2_3_7_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.38.1103"},{"key":"e_1_2_3_8_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.38.1107"},{"key":"e_1_2_3_9_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.38.1677"},{"key":"e_1_2_3_10_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.42.479"},{"key":"e_1_2_3_11_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)74289-4"},{"key":"e_1_2_3_12_1","unstructured":"Ansatrienins;"},{"key":"e_1_2_3_13_2","first-page":"122","volume":"2","author":"Weber F. 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