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This new one\u2010pot protocol yields the ethyl 3\u2010hydroxy\u20102(1<jats:italic>H<\/jats:italic>)\u2010oxoquinoline\u20104\u2010carboxylate core, regioselectively and in good to excellent yields. A DFT mechanistic study indicates metallocarbene formation between the 3\u2010hydroxyindole\u2010diazo intermediate and the dirhodium(II) complex to be the rate\u2010limiting step of the reaction. The synthesized ethyl 3\u2010hydroxy\u20102(1<jats:italic>H<\/jats:italic>)\u2010oxoquinoline\u20104\u2010carboxylate core could be readily converted to viridicatin alkaloids, in yields up to 80\u2009% by a microwave\u2010assisted Suzuki\u2013Miyaura cross coupling of the 3\u2010hydroxy\u20104\u2010bromoquinolin\u20102(1<jats:italic>H<\/jats:italic>)\u2010one with arylboronic acid.<\/jats:p>","DOI":"10.1002\/ejoc.201300796","type":"journal-article","created":{"date-parts":[[2013,8,20]],"date-time":"2013-08-20T06:26:50Z","timestamp":1376980010000},"page":"6280-6290","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":21,"title":["Ring\u2010Expansion Reaction of Isatins with Ethyl Diazoacetate Catalyzed by Dirhodium(II)\/DBU Metal\u2010Organic System: En Route to Viridicatin Alkaloids"],"prefix":"10.1002","volume":"2013","author":[{"given":"Roberta","family":"Paterna","sequence":"first","affiliation":[]},{"given":"V\u00e2nia","family":"Andr\u00e9","sequence":"additional","affiliation":[]},{"given":"M. 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