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dc.contributor.author조천규-
dc.date.accessioned2019-12-10T02:14:16Z-
dc.date.available2019-12-10T02:14:16Z-
dc.date.issued2018-11-
dc.identifier.citationORGANIC LETTERS, v. 20, no. 22, page. 7312-7316en_US
dc.identifier.issn1523-7060-
dc.identifier.issn1523-7052-
dc.identifier.urihttps://pubs.acs.org/doi/10.1021/acs.orglett.8b03250-
dc.identifier.urihttp://repository.hanyang.ac.kr/handle/20.500.11754/120632-
dc.description.abstractAn asymmetric formal total synthesis of (+)-aplykurodinone-1 was achieved using a route, in which hydrogen bonding serves as a stereochemical control element governing the pi-facial selectivity of intramolecular Diels-Alder (IMDA) reaction of an enone tethered 2-pyrone. In the IMDA process, the configuration at a stereogenic, hydroxyl bearing an alpha-carbon in the enone dienophile is conveyed in a highly effective manner through intramolecular hydrogen bonding with the enone carbonyl oxygen. The tricyclic lactone, generated in this process, was successfully converted to a late stage intermediate in Danishefsky's synthesis of aplykurodinone-1.en_US
dc.description.sponsorshipWe thank the National Research Foundation of Korea (2014R1A5A1011165) for funding. We also thank Prof. Hyunwoo Kim at KAIST, Daejeon, Korea for the DFT calculations.en_US
dc.language.isoen_USen_US
dc.publisherAMER CHEMICAL SOCen_US
dc.subjectREGIOSELECTIVE SYNTHESISen_US
dc.subjectDEGRADED STEROLSen_US
dc.subject3,5-DIBROMO-2-PYRONEen_US
dc.subjectCYCLOADDITIONen_US
dc.subject(+/-)-CRININEen_US
dc.subjectOXIDATIONen_US
dc.titleH-Bonding Mediated Asymmetric Intramolecular Diels-Alder Reaction in the Formal Synthesis of (+)-Aplykurodinone-1en_US
dc.typeArticleen_US
dc.relation.no22-
dc.relation.volume20-
dc.identifier.doi10.1021/acs.orglett.8b03250-
dc.relation.page7312-7316-
dc.relation.journalORGANIC LETTERS-
dc.contributor.googleauthorLee, Joon-Ho-
dc.contributor.googleauthorCho, Cheon-Gyu-
dc.relation.code2018001077-
dc.sector.campusS-
dc.sector.daehakCOLLEGE OF NATURAL SCIENCES[S]-
dc.sector.departmentDEPARTMENT OF CHEMISTRY-
dc.identifier.pidccho-
dc.identifier.orcidhttp://orcid.org/0000-0003-4851-5671-
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COLLEGE OF NATURAL SCIENCES[S](자연과학대학) > CHEMISTRY(화학과) > Articles
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