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Article: A tandem metal carbene cyclization-cycloaddition approach to the pseudolaric acids

TitleA tandem metal carbene cyclization-cycloaddition approach to the pseudolaric acids
Authors
Issue Date2003
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc
Citation
Journal Of Organic Chemistry, 2003, v. 68 n. 11, p. 4195-4205 How to Cite?
AbstractAn approach toward the synthesis of the antifungal and cytotoxic pseudolaric acids based on the tandem metal carbene cyclization-cycloaddition reaction is described. Using this strategy, the advanced intermediate 3a bearing three of the four stereocenters of the target molecules has been synthesized. The substrate-controlled diastereoselectivity of the tandem carbene cyclizationcycloaddition was preferential for the undesired diastereomer, but reagent control through the use of Hashimoto's chiral rhodium catalyst Rh 2(S-BPTV) 4 reversed the selectivity in favor of 3a. Ring opening of the oxabicyclic nucleus to give a hydroxycycloheptene has been demonstrated in a model study.
Persistent Identifierhttp://hdl.handle.net/10722/70250
ISSN
2015 Impact Factor: 4.785
2015 SCImago Journal Rankings: 2.095
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorChen, Ben_HK
dc.contributor.authorKo, RYYen_HK
dc.contributor.authorYuen, MSMen_HK
dc.contributor.authorCheng, KFen_HK
dc.contributor.authorChiu, Pen_HK
dc.date.accessioned2010-09-06T06:21:07Z-
dc.date.available2010-09-06T06:21:07Z-
dc.date.issued2003en_HK
dc.identifier.citationJournal Of Organic Chemistry, 2003, v. 68 n. 11, p. 4195-4205en_HK
dc.identifier.issn0022-3263en_HK
dc.identifier.urihttp://hdl.handle.net/10722/70250-
dc.description.abstractAn approach toward the synthesis of the antifungal and cytotoxic pseudolaric acids based on the tandem metal carbene cyclization-cycloaddition reaction is described. Using this strategy, the advanced intermediate 3a bearing three of the four stereocenters of the target molecules has been synthesized. The substrate-controlled diastereoselectivity of the tandem carbene cyclizationcycloaddition was preferential for the undesired diastereomer, but reagent control through the use of Hashimoto's chiral rhodium catalyst Rh 2(S-BPTV) 4 reversed the selectivity in favor of 3a. Ring opening of the oxabicyclic nucleus to give a hydroxycycloheptene has been demonstrated in a model study.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.titleA tandem metal carbene cyclization-cycloaddition approach to the pseudolaric acidsen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0022-3263&volume=68&spage=4195&epage=4205&date=2003&atitle=A+Tandem+Metal+Carbene+Cyclization-Cycloaddition+Approach+to+the+Pseudolaric+Acids+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/jo026399men_HK
dc.identifier.pmid12762718-
dc.identifier.scopuseid_2-s2.0-0038441588en_HK
dc.identifier.hkuros92629en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0038441588&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume68en_HK
dc.identifier.issue11en_HK
dc.identifier.spage4195en_HK
dc.identifier.epage4205en_HK
dc.identifier.isiWOS:000183066100008-
dc.publisher.placeUnited Statesen_HK
dc.identifier.scopusauthoridChen, B=37160914300en_HK
dc.identifier.scopusauthoridKo, RYY=36150930100en_HK
dc.identifier.scopusauthoridYuen, MSM=37162570200en_HK
dc.identifier.scopusauthoridCheng, KF=7402997838en_HK
dc.identifier.scopusauthoridChiu, P=11140148700en_HK

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