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dc.contributor.authorHsu, Shih-Wenen_US
dc.contributor.authorCheng, Hsiu-Yien_US
dc.contributor.authorHuang, An-Chien_US
dc.contributor.authorHo, Tse-Loken_US
dc.contributor.authorHou, Duen-Renen_US
dc.date.accessioned2014-12-08T15:36:06Z-
dc.date.available2014-12-08T15:36:06Z-
dc.date.issued2014-05-01en_US
dc.identifier.issn1434-193Xen_US
dc.identifier.urihttp://dx.doi.org/10.1002/ejoc.201400064en_US
dc.identifier.urihttp://hdl.handle.net/11536/24434-
dc.description.abstractThe total synthesis of quebrachamine was achieved through the macrolactamization of cis-2-alkenylated indole 17, which was prepared by a Sonogashira reaction between indole 5b and piperidine 11 followed by cis-hydrogenation. We found that stoichiometric copper(I) iodide limited the undesired Glaser-type homocoupling of alkyne 11 that would otherwise take place during the Sonogashira coupling. This direct approach allowed the total synthesis in ten linear steps starting from commercially available chemicals. Conditions for the reduction of lactam 19 by lithium aluminiumhydride were adjustable, so that either (+/-)-quebrachamine or the analogue (+/-)-kopsiyunnanine D was prepared.en_US
dc.language.isoen_USen_US
dc.subjectTotal synthesisen_US
dc.subjectNatural productsen_US
dc.subjectAlkaloidsen_US
dc.subjectLactamizationen_US
dc.subjectHydrogenationen_US
dc.titleTotal Synthesis of Quebrachamine through Macrolactamizationen_US
dc.typeArticleen_US
dc.identifier.doi10.1002/ejoc.201400064en_US
dc.identifier.journalEUROPEAN JOURNAL OF ORGANIC CHEMISTRYen_US
dc.citation.volume2014en_US
dc.citation.issue15en_US
dc.citation.spage3109en_US
dc.citation.epage3115en_US
dc.contributor.department應用化學系zh_TW
dc.contributor.departmentDepartment of Applied Chemistryen_US
dc.identifier.wosnumberWOS:000336377000011-
dc.citation.woscount2-
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