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Article: Enantioselective total synthesis of (-)-triptolide, (-)-triptonide, (+)- triptophenolide, and (+)-triptoquinonide

TitleEnantioselective total synthesis of (-)-triptolide, (-)-triptonide, (+)- triptophenolide, and (+)-triptoquinonide
Authors
Issue Date2000
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc
Citation
Journal Of Organic Chemistry, 2000, v. 65 n. 7, p. 2208-2217 How to Cite?
AbstractThe first enantioselective total synthesis of (-)-triptolide (1), (-)- triptonide (2), (+)-triptophenolide (3), and (+)-triptoquinonide (4) was completed. The key step involves lanthanide triflate-catalyzed oxidative radical cyclization of (+)-8-phenylmenthyl ester 30 mediated by Mn(OAc) 3, providing intermediate 31 with good chemical yield (77%) and excellent diastereoselectivity (dr 38:1). (+)Triptophenolide methyl ether (5) was then prepared in >99% enantiomeric excess (>99% ee), and readily converted to natural products 1-4. In addition, transition state models were proposed to explain the opposite chiral induction observed in the oxidative radical cyclization reactions of chiral β-keto esters 17 (without an α-substituent) and 17a (with an α-chloro substituent).
Persistent Identifierhttp://hdl.handle.net/10722/69665
ISSN
2015 Impact Factor: 4.785
2015 SCImago Journal Rankings: 2.095
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorYang, Den_HK
dc.contributor.authorYe, XYen_HK
dc.contributor.authorXu, Men_HK
dc.date.accessioned2010-09-06T06:15:44Z-
dc.date.available2010-09-06T06:15:44Z-
dc.date.issued2000en_HK
dc.identifier.citationJournal Of Organic Chemistry, 2000, v. 65 n. 7, p. 2208-2217en_HK
dc.identifier.issn0022-3263en_HK
dc.identifier.urihttp://hdl.handle.net/10722/69665-
dc.description.abstractThe first enantioselective total synthesis of (-)-triptolide (1), (-)- triptonide (2), (+)-triptophenolide (3), and (+)-triptoquinonide (4) was completed. The key step involves lanthanide triflate-catalyzed oxidative radical cyclization of (+)-8-phenylmenthyl ester 30 mediated by Mn(OAc) 3, providing intermediate 31 with good chemical yield (77%) and excellent diastereoselectivity (dr 38:1). (+)Triptophenolide methyl ether (5) was then prepared in >99% enantiomeric excess (>99% ee), and readily converted to natural products 1-4. In addition, transition state models were proposed to explain the opposite chiral induction observed in the oxidative radical cyclization reactions of chiral β-keto esters 17 (without an α-substituent) and 17a (with an α-chloro substituent).en_HK
dc.languageengen_HK
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/jocen_HK
dc.relation.ispartofJournal of Organic Chemistryen_HK
dc.titleEnantioselective total synthesis of (-)-triptolide, (-)-triptonide, (+)- triptophenolide, and (+)-triptoquinonideen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0022-3263&volume=65&spage=2208&epage=2217&date=2000&atitle=Enantioselective+total+synthesis+of+(-)-triptolide,+(-)-Triptonide,+(+)-Triptophenolide,+and+(+)-triptoquinonideen_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/jo9919613en_HK
dc.identifier.pmid10774048-
dc.identifier.scopuseid_2-s2.0-0034616006en_HK
dc.identifier.hkuros49900en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0034616006&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume65en_HK
dc.identifier.issue7en_HK
dc.identifier.spage2208en_HK
dc.identifier.epage2217en_HK
dc.identifier.isiWOS:000086348400042-
dc.publisher.placeUnited Statesen_HK
dc.identifier.scopusauthoridYang, D=7404800756en_HK
dc.identifier.scopusauthoridYe, XY=36900231000en_HK
dc.identifier.scopusauthoridXu, M=15729771700en_HK

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