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Article: An Expeditious Nazarov Cyclization Strategy toward the Hydroazulene Core of Guanacastepene A

TitleAn Expeditious Nazarov Cyclization Strategy toward the Hydroazulene Core of Guanacastepene A
Authors
Issue Date2004
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/orlef7/index.html
Citation
Organic Letters, 2004, v. 6 n. 4, p. 613-616 How to Cite?
Abstract(Matrix presented) The hydroazulene core of guanacastepene A has been synthesized in five steps from commercially available starting materials using a classical Nazarov cyclization to install the stereochemistry in the cyclopentanone diastereoselectively. In the presence or absence of Lewis bases, a hydroazulenone or a spirocyclic ketone generated via a novel Wagner-Meerwein rearrangement is obtained with excellent selectivity and yield.
Persistent Identifierhttp://hdl.handle.net/10722/69051
ISSN
2015 Impact Factor: 6.732
2015 SCImago Journal Rankings: 3.187
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorChiu, Pen_HK
dc.contributor.authorLi, Sen_HK
dc.date.accessioned2010-09-06T06:10:06Z-
dc.date.available2010-09-06T06:10:06Z-
dc.date.issued2004en_HK
dc.identifier.citationOrganic Letters, 2004, v. 6 n. 4, p. 613-616en_HK
dc.identifier.issn1523-7060en_HK
dc.identifier.urihttp://hdl.handle.net/10722/69051-
dc.description.abstract(Matrix presented) The hydroazulene core of guanacastepene A has been synthesized in five steps from commercially available starting materials using a classical Nazarov cyclization to install the stereochemistry in the cyclopentanone diastereoselectively. In the presence or absence of Lewis bases, a hydroazulenone or a spirocyclic ketone generated via a novel Wagner-Meerwein rearrangement is obtained with excellent selectivity and yield.en_HK
dc.languageengen_HK
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/orlef7/index.htmlen_HK
dc.relation.ispartofOrganic Lettersen_HK
dc.subject.meshAnti-Bacterial Agents - chemical synthesis-
dc.subject.meshCatalysis-
dc.subject.meshCyclization-
dc.subject.meshDiterpenes - chemical synthesis-
dc.subject.meshKetones - chemistry-
dc.titleAn Expeditious Nazarov Cyclization Strategy toward the Hydroazulene Core of Guanacastepene Aen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=1523-7060&volume=6&issue=4&spage=613&epage=616&date=2004&atitle=An+expeditious+Nazarov+cyclization+strategy+toward+the+hydroazulene+core+of+guanacastepene+A++en_HK
dc.identifier.emailChiu, P:pchiu@hku.hken_HK
dc.identifier.authorityChiu, P=rp00680en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/ol036433zen_HK
dc.identifier.pmid14961636-
dc.identifier.scopuseid_2-s2.0-1342332890en_HK
dc.identifier.hkuros92693en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-1342332890&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume6en_HK
dc.identifier.issue4en_HK
dc.identifier.spage613en_HK
dc.identifier.epage616en_HK
dc.identifier.isiWOS:000188926400040-
dc.publisher.placeUnited Statesen_HK
dc.identifier.scopusauthoridChiu, P=11140148700en_HK
dc.identifier.scopusauthoridLi, S=7409245628en_HK

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