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Article: The mechanism of the spontaneous autoxidation of dihydroartemisinic acid

TitleThe mechanism of the spontaneous autoxidation of dihydroartemisinic acid
Authors
Sy, LKBrown, GD
KeywordsAutoxidation
Enols and derivatives
Mechanisms
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. 897-908 How to Cite?
DOI: http://dx.doi.org/10.1016/S0040-4020(01)01193-0
AbstractDihydroartemisinic acid undergoes slow spontaneous autoxidation to artemisinin and other natural products, which have been reported from the medicinal plant Artemisia annua. The mechanism of this complex transformation is shown to involve four steps: (i) initial reaction of the Δ4.5-double bond of dihydroartemisinic acid with molecular oxygen, (ii) Hock cleavage of the resulting tertiary allylic hydroperoxide; (iii) oxygenation of the enol product from Hock cleavage; and (iv) cyclization of the resulting vicinal hydroperoxyl-aldehyde to the 1,2,4-trioxane system of artemisinin. © 2002 Elsevier Science Ltd. All rights reserved.
Persistent Identifierhttp://hdl.handle.net/10722/70193
ISSN
0040-4020
2021 Impact Factor: 2.388
2020 SCImago Journal Rankings: 0.581
ISI Accession Number ID
WOS:000173624300006
References
References in Scopus

 

DC FieldValueLanguage
dc.contributor.authorSy, LKen_HK
dc.contributor.authorBrown, GDen_HK
dc.date.accessioned2010-09-06T06:20:36Z-
dc.date.available2010-09-06T06:20:36Z-
dc.date.issued2002en_HK
dc.identifier.citationTetrahedron, 2002, v. 58 n. 5, p. 897-908en_HK
dc.identifier.issn0040-4020en_HK
dc.identifier.urihttp://hdl.handle.net/10722/70193-
dc.description.abstractDihydroartemisinic acid undergoes slow spontaneous autoxidation to artemisinin and other natural products, which have been reported from the medicinal plant Artemisia annua. The mechanism of this complex transformation is shown to involve four steps: (i) initial reaction of the Δ4.5-double bond of dihydroartemisinic acid with molecular oxygen, (ii) Hock cleavage of the resulting tertiary allylic hydroperoxide; (iii) oxygenation of the enol product from Hock cleavage; and (iv) cyclization of the resulting vicinal hydroperoxyl-aldehyde to the 1,2,4-trioxane system of artemisinin. © 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.subjectEnols and derivativesen_HK
dc.subjectMechanismsen_HK
dc.subjectTerpenes and terpenoidsen_HK
dc.titleThe mechanism of 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=897&epage=908&date=2002&atitle=The+mechanism+of+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)01193-0en_HK
dc.identifier.scopuseid_2-s2.0-0037185534en_HK
dc.identifier.hkuros69034en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0037185534&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume58en_HK
dc.identifier.issue5en_HK
dc.identifier.spage897en_HK
dc.identifier.epage908en_HK
dc.identifier.isiWOS:000173624300006-
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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