Please use this identifier to cite or link to this item: http://hdl.handle.net/10397/95369
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dc.contributorDepartment of Applied Biology and Chemical Technologyen_US
dc.creatorLiang, Xen_US
dc.creatorZhou, Len_US
dc.creatorMin, Len_US
dc.creatorYe, Wen_US
dc.creatorBao, Wen_US
dc.creatorMa, Wen_US
dc.creatorYang, Qen_US
dc.creatorQiao, Fen_US
dc.creatorZhang, Xen_US
dc.creatorLee, CSen_US
dc.date.accessioned2022-09-19T01:59:56Z-
dc.date.available2022-09-19T01:59:56Z-
dc.identifier.issn0022-3263en_US
dc.identifier.urihttp://hdl.handle.net/10397/95369-
dc.language.isoenen_US
dc.publisherAmerican Chemical Societyen_US
dc.rights© 2017 American Chemical Societyen_US
dc.rightsThis document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.6b02921.en_US
dc.titleDiastereoselective total synthesis of (±)-Basiliolide B and (±)-epi-8-Basiliolide Ben_US
dc.typeJournal/Magazine Articleen_US
dc.identifier.spage3463en_US
dc.identifier.epage3481en_US
dc.identifier.volume82en_US
dc.identifier.issue7en_US
dc.identifier.doi10.1021/acs.joc.6b02921en_US
dcterms.abstractThe C8 and C9 stereogenic centers of the basiliolide/transtaganolide family have been established stereoselectively using a cyclopropane ring-opening strategy, which has been studied by DFT calculations of a variety of lithium-chelating models. The highly functionalized intermediates obtained in this strategy were successfully employed for the diastereoselective total synthesis of (±)-basiliolide B and (±)-epi-8-basiliolide B. The decalin core with a lactone bridge was constructed via a 2-pyrone Diels-Alder (DA) cycloaddition, and the unprecedented seven-membered acyl ketene acetal was established by a biomimetic intramolecular O-acylation cyclization.en_US
dcterms.accessRightsopen accessen_US
dcterms.bibliographicCitationJournal of organic chemistry, 7 Apr. 2017, v. 82, no. 7, p. 3463-3481en_US
dcterms.isPartOfJournal of organic chemistryen_US
dcterms.issued2017-04-07-
dc.identifier.scopus2-s2.0-85017168302-
dc.identifier.pmid28252297-
dc.identifier.eissn1520-6904en_US
dc.description.oaAccepted Manuscripten_US
dc.identifier.FolderNumberRGC-B2-1532-
dc.description.fundingSourceRGCen_US
dc.description.fundingSourceOthersen_US
dc.description.fundingTextthe National Natural Science Foundation of China; Ministry of Science and Technology of China; Shenzhen Science, Technology and Innovation Committee; the Peking University Shenzhen Graduate Schoolen_US
dc.description.pubStatusPublisheden_US
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