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Article: Structure elucidation of arteannuin O, a novel cadinane diol from Artemisia annua, and the synthesis of arteannuins K, L, M and O

TitleStructure elucidation of arteannuin O, a novel cadinane diol from Artemisia annua, and the synthesis of arteannuins K, L, M and O
Authors
Keywords2D NMR
Arteannuin K
Arteannuin L
Arteannuin M
Arteannuin O
Artemisia annua
Artemisinin
Cadinane
Dihydro-epi-deoxyarteannuin B
Mosher ester
X-ray crystallography
Issue Date2001
PublisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/tet
Citation
Tetrahedron, 2001, v. 57 n. 40, p. 8481-8493 How to Cite?
AbstractThe novel cadinane diol, arteannuin O (1), has been obtained from Artemisia annua and its structure has been established by 2D NMR and X-ray crystallography. A reconstructive synthesis of arteannuin O from artemisinin is described, which also yields the natural products arteannuin K and arteannuin L. Mechanistic considerations have led to the conclusion that the stereochemistry of the 5-hydroxyl group was wrongly assigned when arteannuins K, L and M were first reported as natural products. This was confirmed by derivatization of synthetic arteannuins K, L and M as their Mosher esters. © 2001 Elsevier Science Ltd. All rights reserved.
Persistent Identifierhttp://hdl.handle.net/10722/70345
ISSN
2015 Impact Factor: 2.645
2015 SCImago Journal Rankings: 0.991
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorSy, LKen_HK
dc.contributor.authorCheung, KKen_HK
dc.contributor.authorZhu, NYen_HK
dc.contributor.authorBrown, GDen_HK
dc.date.accessioned2010-09-06T06:22:00Z-
dc.date.available2010-09-06T06:22:00Z-
dc.date.issued2001en_HK
dc.identifier.citationTetrahedron, 2001, v. 57 n. 40, p. 8481-8493en_HK
dc.identifier.issn0040-4020en_HK
dc.identifier.urihttp://hdl.handle.net/10722/70345-
dc.description.abstractThe novel cadinane diol, arteannuin O (1), has been obtained from Artemisia annua and its structure has been established by 2D NMR and X-ray crystallography. A reconstructive synthesis of arteannuin O from artemisinin is described, which also yields the natural products arteannuin K and arteannuin L. Mechanistic considerations have led to the conclusion that the stereochemistry of the 5-hydroxyl group was wrongly assigned when arteannuins K, L and M were first reported as natural products. This was confirmed by derivatization of synthetic arteannuins K, L and M as their Mosher esters. © 2001 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.subject2D NMRen_HK
dc.subjectArteannuin Ken_HK
dc.subjectArteannuin Len_HK
dc.subjectArteannuin Men_HK
dc.subjectArteannuin Oen_HK
dc.subjectArtemisia annuaen_HK
dc.subjectArtemisininen_HK
dc.subjectCadinaneen_HK
dc.subjectDihydro-epi-deoxyarteannuin Ben_HK
dc.subjectMosher esteren_HK
dc.subjectX-ray crystallographyen_HK
dc.titleStructure elucidation of arteannuin O, a novel cadinane diol from Artemisia annua, and the synthesis of arteannuins K, L, M and Oen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0040-4020&volume=57&spage=8481&epage=8493&date=2001&atitle=Structure+elucidation+of+arteannuin+O,+a+novel+cadinane+diol+from+Artemisia+annua,+and+the+synthesis+of+arteannuins+K,+L,+M+and+Oen_HK
dc.identifier.emailSy, LK: sylk@hku.hken_HK
dc.identifier.emailZhu, NY: nzhu@hkucc.hku.hken_HK
dc.identifier.authoritySy, LK=rp00784en_HK
dc.identifier.authorityZhu, NY=rp00845en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1016/S0040-4020(01)00633-0en_HK
dc.identifier.scopuseid_2-s2.0-0035478822en_HK
dc.identifier.hkuros68643en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0035478822&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume57en_HK
dc.identifier.issue40en_HK
dc.identifier.spage8481en_HK
dc.identifier.epage8493en_HK
dc.identifier.isiWOS:000171327500008-
dc.publisher.placeUnited Kingdomen_HK
dc.identifier.scopusauthoridSy, LK=35874602700en_HK
dc.identifier.scopusauthoridCheung, KK=7402406613en_HK
dc.identifier.scopusauthoridZhu, NY=7201449530en_HK
dc.identifier.scopusauthoridBrown, GD=7406468149en_HK

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