{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,19]],"date-time":"2026-06-19T23:42:47Z","timestamp":1781912567461,"version":"3.54.5"},"reference-count":31,"publisher":"Wiley","issue":"22","license":[{"start":{"date-parts":[[2017,4,5]],"date-time":"2017-04-05T00:00:00Z","timestamp":1491350400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["EXC62"],"award-info":[{"award-number":["EXC62"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100005156","name":"Alexander von Humboldt-Stiftung","doi-asserted-by":"publisher","award":["Scholarship"],"award-info":[{"award-number":["Scholarship"]}],"id":[{"id":"10.13039\/100005156","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2017,4,19]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The polyketide, 20\u2010deoxy elansolid B1, was prepared by a convergent strategy that relied on a putative biomimetic intramolecular Diels\u2013Alder cycloaddition (IMDA) via a vinylic <jats:italic>p<\/jats:italic>\u2010quinone methide intermediate to furnish the key tetrahydroindane unit. The (<jats:italic>Z<\/jats:italic>,<jats:italic>E<\/jats:italic>,<jats:italic>Z<\/jats:italic>)\u2010configured triene unit was constructed by Pd\u2010catalyzed Suzuki\u2013Miyaura and Stille cross\u2010coupling reactions without isomerization of any of the olefinic double bonds. Formation of a <jats:italic>p<\/jats:italic>\u2010methide quinone intermediate under basic conditions and subsequent Michael addition by water to this intermediate proceeded with high facial selectivity which terminated this total synthesis. Remarkably, the new elansolid derivative <jats:bold>2\u2009c<\/jats:bold> shows very good inhibitory effect against <jats:italic>Bacillus subtilis<\/jats:italic> and <jats:italic>Staphylococcus aureus<\/jats:italic> (including MRSA) similarly to the best elansolid derivatives reported so far. Consequently, the hydroxyl group at C20 is not essential for antibacterial activity.<\/jats:p>","DOI":"10.1002\/chem.201605884","type":"journal-article","created":{"date-parts":[[2017,2,13]],"date-time":"2017-02-13T06:06:48Z","timestamp":1486966008000},"page":"5291-5298","source":"Crossref","is-referenced-by-count":20,"title":["Harnessing a <i>p<\/i>\u2010Quinone Methide Intermediate in the Biomimetic Total Synthesis of the Highly Active Antibiotic 20\u2010Deoxy\u2010Elansolid B1"],"prefix":"10.1002","volume":"23","author":[{"given":"Liang Liang","family":"Wang","sequence":"first","affiliation":[{"name":"Institut f\u00fcr Organische Chemie und Biomolekulares Wirkstoffzentrum (BMWZ) Leibniz Universit\u00e4t Hannover  Schneiderberg 1B 30167 Hannover Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"David","family":"Candito","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Organische Chemie und Biomolekulares Wirkstoffzentrum (BMWZ) Leibniz Universit\u00e4t Hannover  Schneiderberg 1B 30167 Hannover Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gerald","family":"Dr\u00e4ger","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Organische Chemie und Biomolekulares Wirkstoffzentrum (BMWZ) Leibniz Universit\u00e4t Hannover  Schneiderberg 1B 30167 Hannover Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jennifer","family":"Herrmann","sequence":"additional","affiliation":[{"name":"Helmholtz Zentrum f\u00fcr Infektionsforschung Helmholtz Institut f\u00fcr Pharmazeutische Forschung Saarland und Pharmazeutische Biotechnologie Universit\u00e4t des Saarlandes  Campus E 8.1 66123 Saarbr\u00fccken Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rolf","family":"M\u00fcller","sequence":"additional","affiliation":[{"name":"Helmholtz Zentrum f\u00fcr Infektionsforschung Helmholtz Institut f\u00fcr Pharmazeutische Forschung Saarland und Pharmazeutische Biotechnologie Universit\u00e4t des Saarlandes  Campus E 8.1 66123 Saarbr\u00fccken Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Andreas","family":"Kirschning","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Organische Chemie und Biomolekulares Wirkstoffzentrum (BMWZ) Leibniz Universit\u00e4t Hannover  Schneiderberg 1B 30167 Hannover Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2017,4,5]]},"reference":[{"key":"e_1_2_6_1_1","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"crossref","unstructured":"K.Gerth H.Steimetz G.H\u00f6fle 2009 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After separation both diastereoisomers provided crystals for X-ray analysis:rac-35\u2009a:CCDC\u20051515807\u2005(rac-35\u2009a) and 1515804\u2005(rac-35\u2009b) contain the supplementary crystallographic data for this paper. These data are provided free of charge byThe Cambridge Crystallographic Data Centre."},{"key":"e_1_2_6_26_1","unstructured":"Other coupling strategies such as Stille cross-coupling reaction between vinyl stannane38and vinyl iodide35\u2009aas well as Suzuki\u2013Miyaura cross-coupling between diene boronate39and11were unsuccessful (see Scheme below and Supporting Information)."},{"key":"e_1_2_6_27_1","unstructured":"The presence of the phenolic acetyl ester is crucial for the smooth cleavage of the benzylic acetoxy group at C25 under the given condition. 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