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Article: Investigation of Mn(III)-based oxidative free radical cyclization reactions toward the synthesis of triptolide: The effects of lanthanide triflates and substituents on stereoselectivity

TitleInvestigation of Mn(III)-based oxidative free radical cyclization reactions toward the synthesis of triptolide: The effects of lanthanide triflates and substituents on stereoselectivity
Authors
Issue Date2000
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/jacsat/index.html
Citation
Journal Of The American Chemical Society, 2000, v. 122 n. 8, p. 1658-1663 How to Cite?
AbstractMn(III)-mediated oxidative free radical cyclization reactions are useful for construction of polycyclic compounds. In the total synthesis of triptolide (3) and its related compounds, construction of tricyclic skeletons 4 and 5 was achieved by the Mn(OAc) 3-mediated oxidative radical cyclization of a series of acyclic precursors 6-9. The addition of a catalytic amount of lanthanide triflates was found to significantly improve the rate and stereoselectivity of those radical cyclization reactions. The effects of the benzylic oxygen substituents and α-substituents (chloro and methyl) on the radical cyclization reactions were also investigated. Transition-state models were proposed to explain the observed stereoselectivity.
Persistent Identifierhttp://hdl.handle.net/10722/69778
ISSN
2015 Impact Factor: 13.038
2015 SCImago Journal Rankings: 7.123
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorYang, Den_HK
dc.contributor.authorYe, XYen_HK
dc.contributor.authorXu, Men_HK
dc.contributor.authorPang, KWen_HK
dc.contributor.authorCheung, KKen_HK
dc.date.accessioned2010-09-06T06:16:45Z-
dc.date.available2010-09-06T06:16:45Z-
dc.date.issued2000en_HK
dc.identifier.citationJournal Of The American Chemical Society, 2000, v. 122 n. 8, p. 1658-1663en_HK
dc.identifier.issn0002-7863en_HK
dc.identifier.urihttp://hdl.handle.net/10722/69778-
dc.description.abstractMn(III)-mediated oxidative free radical cyclization reactions are useful for construction of polycyclic compounds. In the total synthesis of triptolide (3) and its related compounds, construction of tricyclic skeletons 4 and 5 was achieved by the Mn(OAc) 3-mediated oxidative radical cyclization of a series of acyclic precursors 6-9. The addition of a catalytic amount of lanthanide triflates was found to significantly improve the rate and stereoselectivity of those radical cyclization reactions. The effects of the benzylic oxygen substituents and α-substituents (chloro and methyl) on the radical cyclization reactions were also investigated. Transition-state models were proposed to explain the observed stereoselectivity.en_HK
dc.languageengen_HK
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/jacsat/index.htmlen_HK
dc.relation.ispartofJournal of the American Chemical Societyen_HK
dc.titleInvestigation of Mn(III)-based oxidative free radical cyclization reactions toward the synthesis of triptolide: The effects of lanthanide triflates and substituents on stereoselectivityen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0002-7863&volume=122&issue=8&spage=1658&epage=1663&date=2000&atitle=Investigation+of+Mn(III)-based+oxidative+free+radical+cyclization+reactions+toward+the+synthesis+of+triptolide:++The+effects+of+lanthanide+triflates+and+substituents+on+stereoselectivityen_HK
dc.identifier.emailYang, D:yangdan@hku.hken_HK
dc.identifier.authorityYang, D=rp00825en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/ja993598nen_HK
dc.identifier.scopuseid_2-s2.0-0034050738en_HK
dc.identifier.hkuros49898en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0034050738&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume122en_HK
dc.identifier.issue8en_HK
dc.identifier.spage1658en_HK
dc.identifier.epage1663en_HK
dc.identifier.isiWOS:000085629600012-
dc.publisher.placeUnited Statesen_HK
dc.identifier.scopusauthoridYang, D=7404800756en_HK
dc.identifier.scopusauthoridYe, XY=36900231000en_HK
dc.identifier.scopusauthoridXu, M=15729771700en_HK
dc.identifier.scopusauthoridPang, KW=7101856033en_HK
dc.identifier.scopusauthoridCheung, KK=7402406613en_HK

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