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Article: An adventure in synthesis inspired by the pseudolaric acids

TitleAn adventure in synthesis inspired by the pseudolaric acids
Authors
KeywordsCarbonyl Ylide
Copper Hydride
Cycloaddition
Pseudolaric Acid
Reductive Aldol
Rhodium Carbene
Issue Date2012
Citation
Strategies And Tactics In Organic Synthesis, 2012, v. 8, p. 55-78 How to Cite?
AbstractThis account describes efforts that culminated in the first total synthesis of pseudolaric acid A, an antitumor and antiangiogenic natural product. A first retrosynthesis based on a reductive aldol reaction failed to generate the desired carboskeleton with the correct relative stereochemistry, although the copper hydride-induced reductive aldol cyclization developed for this key step turned out to be a useful synthetic methodology on its own. A second retrosynthesis based on the carbene cyclization cycloaddition cascade reaction as the key step was ultimately successful in constructing pseudolaric acid A, as well as other natural products.
DescriptionAlso book chapter: An Adventure in Synthesis Inspired by the Pseudolaric Acids. In M. Harmata (Eds.), Strategies and Tactics in Organic Synthesis, v. 8, p. 55-78. San Diego, USA: Academic Press, 2012
Persistent Identifierhttp://hdl.handle.net/10722/168664
ISSN
2015 SCImago Journal Rankings: 0.265
References

 

DC FieldValueLanguage
dc.contributor.authorChiu, Pen_US
dc.date.accessioned2012-10-08T03:24:09Z-
dc.date.available2012-10-08T03:24:09Z-
dc.date.issued2012en_US
dc.identifier.citationStrategies And Tactics In Organic Synthesis, 2012, v. 8, p. 55-78en_US
dc.identifier.issn1874-6004en_US
dc.identifier.urihttp://hdl.handle.net/10722/168664-
dc.descriptionAlso book chapter: An Adventure in Synthesis Inspired by the Pseudolaric Acids. In M. Harmata (Eds.), Strategies and Tactics in Organic Synthesis, v. 8, p. 55-78. San Diego, USA: Academic Press, 2012-
dc.description.abstractThis account describes efforts that culminated in the first total synthesis of pseudolaric acid A, an antitumor and antiangiogenic natural product. A first retrosynthesis based on a reductive aldol reaction failed to generate the desired carboskeleton with the correct relative stereochemistry, although the copper hydride-induced reductive aldol cyclization developed for this key step turned out to be a useful synthetic methodology on its own. A second retrosynthesis based on the carbene cyclization cycloaddition cascade reaction as the key step was ultimately successful in constructing pseudolaric acid A, as well as other natural products.-
dc.languageengen_US
dc.relation.ispartofStrategies and Tactics in Organic Synthesisen_US
dc.subjectCarbonyl Ylideen_US
dc.subjectCopper Hydrideen_US
dc.subjectCycloadditionen_US
dc.subjectPseudolaric Aciden_US
dc.subjectReductive Aldolen_US
dc.subjectRhodium Carbeneen_US
dc.titleAn adventure in synthesis inspired by the pseudolaric acidsen_US
dc.typeArticleen_US
dc.identifier.emailChiu, P:pchiu@hku.hken_US
dc.identifier.authorityChiu, P=rp00680en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1016/B978-0-12-386540-3.00003-4en_US
dc.identifier.scopuseid_2-s2.0-84864487719en_US
dc.identifier.hkuros212655-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-84864487719&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume8en_US
dc.identifier.spage55en_US
dc.identifier.epage78en_US
dc.identifier.scopusauthoridChiu, P=11140148700en_US

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