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Article: The role of the 12-carboxylic acid group in the spontaneous autoxidation of dihydroartemisinic acid

TitleThe role of the 12-carboxylic acid group in the spontaneous autoxidation of dihydroartemisinic acid
Authors
Sy, LKBrown, GD
KeywordsAutoxidation
Biomimetic reactions
Mechanism
Terpenes and terpenoids
Issue Date2002
PublisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/tet
Citation
Tetrahedron, 2002, v. 58 n. 5, p. 909-923 How to Cite?
DOI: http://dx.doi.org/10.1016/S0040-4020(01)01192-9
AbstractThree of the four steps in the slow spontaneous autoxidation of dihydroartemisinic acid to artemisinin ('ene-type' reaction of molecular oxygen with the Δ4,5 double bond, Hock cleavage of the resulting tertiary allylic hydroperoxide, oxygenation of the enol product from Hock cleavage and cyclization of the resulting vicinal hydroperoxyl-aldehyde to the 1,2,4-trioxane system of artemisinin) are shown to be assisted by the proximity of the 12-carboxylic acid functional group in dihydroartemisinic acid to the functional groups participating in these reactions. © 2002 Elsevier Science Ltd. All rights reserved.
Persistent Identifierhttp://hdl.handle.net/10722/69982
ISSN
0040-4020
2023 Impact Factor: 2.1
2023 SCImago Journal Rankings: 0.406
ISI Accession Number ID
WOS:000173624300007
References
References in Scopus

 

DC FieldValueLanguage
dc.contributor.authorSy, LKen_HK
dc.contributor.authorBrown, GDen_HK
dc.date.accessioned2010-09-06T06:18:37Z-
dc.date.available2010-09-06T06:18:37Z-
dc.date.issued2002en_HK
dc.identifier.citationTetrahedron, 2002, v. 58 n. 5, p. 909-923en_HK
dc.identifier.issn0040-4020en_HK
dc.identifier.urihttp://hdl.handle.net/10722/69982-
dc.description.abstractThree of the four steps in the slow spontaneous autoxidation of dihydroartemisinic acid to artemisinin ('ene-type' reaction of molecular oxygen with the Δ4,5 double bond, Hock cleavage of the resulting tertiary allylic hydroperoxide, oxygenation of the enol product from Hock cleavage and cyclization of the resulting vicinal hydroperoxyl-aldehyde to the 1,2,4-trioxane system of artemisinin) are shown to be assisted by the proximity of the 12-carboxylic acid functional group in dihydroartemisinic acid to the functional groups participating in these reactions. © 2002 Elsevier Science Ltd. All rights reserved.en_HK
dc.languageengen_HK
dc.publisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/teten_HK
dc.relation.ispartofTetrahedronen_HK
dc.subjectAutoxidationen_HK
dc.subjectBiomimetic reactionsen_HK
dc.subjectMechanismen_HK
dc.subjectTerpenes and terpenoidsen_HK
dc.titleThe role of the 12-carboxylic acid group in the spontaneous autoxidation of dihydroartemisinic aciden_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0040-4020&volume=58&spage=909&epage=923&date=2002&atitle=The+role+of+the+12-carboxylic+acid+group+in+the+spontaneous+autoxidation+of+dihydroartemisinic+aciden_HK
dc.identifier.emailSy, LK:sylk@hkucc.hku.hken_HK
dc.identifier.authoritySy, LK=rp00784en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1016/S0040-4020(01)01192-9en_HK
dc.identifier.scopuseid_2-s2.0-0037185357en_HK
dc.identifier.hkuros69033en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0037185357&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume58en_HK
dc.identifier.issue5en_HK
dc.identifier.spage909en_HK
dc.identifier.epage923en_HK
dc.identifier.isiWOS:000173624300007-
dc.publisher.placeUnited Kingdomen_HK
dc.identifier.scopusauthoridSy, LK=35874602700en_HK
dc.identifier.scopusauthoridBrown, GD=7406468149en_HK
dc.identifier.issnl0040-4020-

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