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Conference Paper: Studies toward an improved synthesis of anti-tumour natural products pseudolaric acids A and B

TitleStudies toward an improved synthesis of anti-tumour natural products pseudolaric acids A and B
Authors
Issue Date2013
PublisherFMC 2013.
Citation
The 2013 Frontiers in Medicinal Chemistry (FMC 2013), San Francisco, CA., 23-26 June 2013. In Abstracts Book, 2013, p. 106 How to Cite?
AbstractOur group has reported the first total synthesis of pseudolaric acid A.2 However, the key step of the carbene cyclization cycloaddition cascade (CCCC) reaction does not give an ideal result, in which the dr of the reaction is only 1.6:1. The CCCC reaction can be understood on the basis of frontier molecular orbital energies. An additional carbonyl group (such as CO2Me) will reduce the energy level of LUMO (dipole) orbital, thus the energy gap between the LUMO (dipole) and the HOMO (dipolarophile) is decreased.3 The interaction should be energetically more favourable and the dr value is anticipated to improve. With modified electronic properties or substrates, alternative Rh(II) catalysts to promote the reaction were examined. We will report on our progress in a model study and improved second generation strategy toward the total synthesis of pseudolaric acids A and B.
DescriptionPoster 64
The Abstracts Book's web site is located at http://wizard.musc.edu/Frontiers%202013%20Abstract%20Booklet.pdf
Persistent Identifierhttp://hdl.handle.net/10722/186638

 

DC FieldValueLanguage
dc.contributor.authorLi, Ben_US
dc.contributor.authorChiu, Pen_US
dc.date.accessioned2013-08-20T12:16:17Z-
dc.date.available2013-08-20T12:16:17Z-
dc.date.issued2013en_US
dc.identifier.citationThe 2013 Frontiers in Medicinal Chemistry (FMC 2013), San Francisco, CA., 23-26 June 2013. In Abstracts Book, 2013, p. 106en_US
dc.identifier.urihttp://hdl.handle.net/10722/186638-
dc.descriptionPoster 64-
dc.descriptionThe Abstracts Book's web site is located at http://wizard.musc.edu/Frontiers%202013%20Abstract%20Booklet.pdf-
dc.description.abstractOur group has reported the first total synthesis of pseudolaric acid A.2 However, the key step of the carbene cyclization cycloaddition cascade (CCCC) reaction does not give an ideal result, in which the dr of the reaction is only 1.6:1. The CCCC reaction can be understood on the basis of frontier molecular orbital energies. An additional carbonyl group (such as CO2Me) will reduce the energy level of LUMO (dipole) orbital, thus the energy gap between the LUMO (dipole) and the HOMO (dipolarophile) is decreased.3 The interaction should be energetically more favourable and the dr value is anticipated to improve. With modified electronic properties or substrates, alternative Rh(II) catalysts to promote the reaction were examined. We will report on our progress in a model study and improved second generation strategy toward the total synthesis of pseudolaric acids A and B.-
dc.languageengen_US
dc.publisherFMC 2013.-
dc.relation.ispartofFrontiers in Medicinal Chemistry, FMC 2013 Abstracts Booken_US
dc.rightsCreative Commons: Attribution 3.0 Hong Kong License-
dc.titleStudies toward an improved synthesis of anti-tumour natural products pseudolaric acids A and Ben_US
dc.typeConference_Paperen_US
dc.identifier.emailChiu, P: pchiu@hku.hken_US
dc.identifier.authorityChiu, P=rp00680en_US
dc.description.naturepostprint-
dc.identifier.hkuros217396en_US
dc.identifier.spage106-
dc.identifier.epage106-
dc.publisher.placeUnited Statesen_US

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