000864465 001__ 864465 000864465 005__ 20210130002601.0 000864465 0247_ $$2doi$$a10.1016/j.bmc.2019.04.033 000864465 0247_ $$2ISSN$$a0968-0896 000864465 0247_ $$2ISSN$$a1464-3391 000864465 0247_ $$2pmid$$apmid:31072649 000864465 0247_ $$2WOS$$aWOS:000470106900027 000864465 037__ $$aFZJ-2019-04246 000864465 041__ $$aEnglish 000864465 082__ $$a610 000864465 1001_ $$0P:(DE-Juel1)165893$$aMechsner, Bastian$$b0 000864465 245__ $$aEnantioselective total synthesis of altersolanol A and N 000864465 260__ $$aAmsterdam [u.a.]$$bElsevier$$c2019 000864465 3367_ $$2DRIVER$$aarticle 000864465 3367_ $$2DataCite$$aOutput Types/Journal article 000864465 3367_ $$0PUB:(DE-HGF)16$$2PUB:(DE-HGF)$$aJournal Article$$bjournal$$mjournal$$s1582038691_32444 000864465 3367_ $$2BibTeX$$aARTICLE 000864465 3367_ $$2ORCID$$aJOURNAL_ARTICLE 000864465 3367_ $$00$$2EndNote$$aJournal Article 000864465 520__ $$aThe development of the first enantioselective total synthesis of altersolanol N is reported. The decisive step of the synthesis is the enantioselective formation of the tetrahydroanthraquinone nucleus by a [4 + 2]-cycloaddition in high yield and with excellent diastereo- and enantioselectivity (>95:5 dr and 95:5 er). In addition, a demanding selective monoacetylation of the OH group at the C-2 position was achieved: an epoxide ring opening with the participation of a neighbouring acetyl group could be established. The route proved to be an efficient alternative to also access enantiomerically pure altersolanol A. 000864465 536__ $$0G:(DE-HGF)POF3-581$$a581 - Biotechnology (POF3-581)$$cPOF3-581$$fPOF III$$x0 000864465 588__ $$aDataset connected to CrossRef 000864465 7001_ $$0P:(DE-Juel1)139024$$aBöse, Dietrich$$b1 000864465 7001_ $$0P:(DE-Juel1)169329$$aHogenkamp, Fabian$$b2 000864465 7001_ $$0P:(DE-HGF)0$$aLedermann, Nadia$$b3 000864465 7001_ $$0P:(DE-Juel1)132001$$aHartmann, Rudolf$$b4 000864465 7001_ $$0P:(DE-Juel1)165763$$aBochinsky, Kevin$$b5 000864465 7001_ $$0P:(DE-HGF)0$$aFrey, Wolfgang$$b6 000864465 7001_ $$0P:(DE-Juel1)128906$$aPietruszka, Jörg$$b7$$eCorresponding author 000864465 773__ $$0PERI:(DE-600)1501507-5$$a10.1016/j.bmc.2019.04.033$$gVol. 27, no. 13, p. 2991 - 2997$$n13$$p2991 - 2997$$tBioorganic & medicinal chemistry$$v27$$x0968-0896$$y2019 000864465 909CO $$ooai:juser.fz-juelich.de:864465$$pVDB 000864465 9101_ $$0I:(DE-588b)5008462-8$$6P:(DE-Juel1)165893$$aForschungszentrum Jülich$$b0$$kFZJ 000864465 9101_ $$0I:(DE-588b)5008462-8$$6P:(DE-Juel1)139024$$aForschungszentrum Jülich$$b1$$kFZJ 000864465 9101_ $$0I:(DE-588b)5008462-8$$6P:(DE-Juel1)169329$$aForschungszentrum Jülich$$b2$$kFZJ 000864465 9101_ $$0I:(DE-HGF)0$$6P:(DE-HGF)0$$a Heinrich-Heine-Universität Düsseldorf$$b3 000864465 9101_ $$0I:(DE-588b)5008462-8$$6P:(DE-Juel1)132001$$aForschungszentrum Jülich$$b4$$kFZJ 000864465 9101_ $$0I:(DE-588b)5008462-8$$6P:(DE-Juel1)165763$$aForschungszentrum Jülich$$b5$$kFZJ 000864465 9101_ $$0I:(DE-HGF)0$$6P:(DE-HGF)0$$a Universität Stuttgart$$b6 000864465 9101_ $$0I:(DE-588b)5008462-8$$6P:(DE-Juel1)128906$$aForschungszentrum Jülich$$b7$$kFZJ 000864465 9101_ $$0I:(DE-HGF)0$$6P:(DE-Juel1)128906$$a Heinrich-Heine-Universität Düsseldorf$$b7 000864465 9131_ $$0G:(DE-HGF)POF3-581$$1G:(DE-HGF)POF3-580$$2G:(DE-HGF)POF3-500$$3G:(DE-HGF)POF3$$4G:(DE-HGF)POF$$aDE-HGF$$bKey Technologies$$lKey Technologies for the Bioeconomy$$vBiotechnology$$x0 000864465 9141_ $$y2019 000864465 915__ $$0StatID:(DE-HGF)0420$$2StatID$$aNationallizenz 000864465 915__ $$0StatID:(DE-HGF)0200$$2StatID$$aDBCoverage$$bSCOPUS 000864465 915__ $$0StatID:(DE-HGF)0300$$2StatID$$aDBCoverage$$bMedline 000864465 915__ $$0StatID:(DE-HGF)0310$$2StatID$$aDBCoverage$$bNCBI Molecular Biology Database 000864465 915__ $$0StatID:(DE-HGF)0100$$2StatID$$aJCR$$bBIOORGAN MED CHEM : 2017 000864465 915__ $$0StatID:(DE-HGF)0600$$2StatID$$aDBCoverage$$bEbsco Academic Search 000864465 915__ $$0StatID:(DE-HGF)0030$$2StatID$$aPeer Review$$bASC 000864465 915__ $$0StatID:(DE-HGF)0199$$2StatID$$aDBCoverage$$bClarivate Analytics Master Journal List 000864465 915__ $$0StatID:(DE-HGF)0110$$2StatID$$aWoS$$bScience Citation Index 000864465 915__ $$0StatID:(DE-HGF)0150$$2StatID$$aDBCoverage$$bWeb of Science Core Collection 000864465 915__ $$0StatID:(DE-HGF)0111$$2StatID$$aWoS$$bScience Citation Index Expanded 000864465 915__ $$0StatID:(DE-HGF)1030$$2StatID$$aDBCoverage$$bCurrent Contents - Life Sciences 000864465 915__ $$0StatID:(DE-HGF)1050$$2StatID$$aDBCoverage$$bBIOSIS Previews 000864465 915__ $$0StatID:(DE-HGF)9900$$2StatID$$aIF < 5 000864465 920__ $$lyes 000864465 9201_ $$0I:(DE-Juel1)IBOC-20090406$$kIBOC$$lInstitut für Bioorganische Chemie (HHUD)$$x0 000864465 9201_ $$0I:(DE-Juel1)IBG-1-20101118$$kIBG-1$$lBiotechnologie$$x1 000864465 9201_ $$0I:(DE-Juel1)ICS-6-20110106$$kICS-6$$lStrukturbiochemie$$x2 000864465 980__ $$ajournal 000864465 980__ $$aVDB 000864465 980__ $$aI:(DE-Juel1)IBOC-20090406 000864465 980__ $$aI:(DE-Juel1)IBG-1-20101118 000864465 980__ $$aI:(DE-Juel1)ICS-6-20110106 000864465 980__ $$aUNRESTRICTED 000864465 981__ $$aI:(DE-Juel1)IBI-7-20200312