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The mechanism of this transformation was probed, yielding insight that enabled cross\u2010coupling trimerizations. With this method, the natural product pyrolaside\u2005B was synthesized for the first time. The key strategy used for this novel synthesis is the facile one\u2010step construction of a spiroketal trimer intermediate, which can be selectively reduced to give the natural product framework without recourse to stepwise Ullmann\u2010 and Suzuki\u2010type couplings. As a result, pyrolaside\u2005B can be obtained expeditiously in five steps and 16\u2009% overall yield. Three other analogues were synthesized, thus highlighting the utility of the method, which provides new accessibility to this area of chemical space. A novel xanthene was also synthesized through controlled Lewis acid promoted rearrangement of a spiroketal trimer.<\/jats:p>","DOI":"10.1002\/anie.201915654","type":"journal-article","created":{"date-parts":[[2020,2,5]],"date-time":"2020-02-05T21:52:55Z","timestamp":1580939575000},"page":"7842-7847","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":20,"title":["Total Synthesis of Pyrolaside B: Phenol Trimerization through Sequenced Oxidative C\u2212C and C\u2212O Coupling"],"prefix":"10.1002","volume":"59","author":[{"given":"Erika","family":"Neuhaus","sequence":"first","affiliation":[{"name":"Department of Chemistry University of Pennsylvania  Philadelphia PA 19104 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4225-7125","authenticated-orcid":false,"given":"Marisa C.","family":"Kozlowski","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of 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