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Article: Determination of the absolute stereochemistry of the epoxide group in alpinia epoxide by NMR

TitleDetermination of the absolute stereochemistry of the epoxide group in alpinia epoxide by NMR
Authors
Sy, LKBrown, GD
Keywords14,15-epoxylabda- 8(17),12-dien-16-al (E)
Absolute stereochemistry
Alpina epoxide
Alpinia chinensis
Mosher ester, two-dimensional NMR
S(+)/R(-) MTPCl
Zingiberaceae
Issue Date1998
PublisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/phytochem
Citation
Phytochemistry, 1998, v. 49 n. 6, p. 1741-1744 How to Cite?
DOI: http://dx.doi.org/10.1016/S0031-9422(98)00298-2
AbstractThe absolute stereochemistry of the epoxide group in alpinia epoxide [14,15-epoxylabda-8(17),12-dien-16-al (E)] has been determined by simultaneous reduction of the aldehyde and epoxide functional groups in this molecule to primary and secondary alcohols, followed by selective protection of the primary alcohol and derivitization of the secondary alcohol with S(+) and R(-) MTPCl as Mosher esters. Changes in 1H NMR chemical shifts for all positions in these two esters were determined by 2D-NMR and used to infer the absolute stereochemistry of the epoxide group in the natural product alpinia epoxide.
Persistent Identifierhttp://hdl.handle.net/10722/69467
ISSN
0031-9422
2023 Impact Factor: 3.2
2023 SCImago Journal Rankings: 0.667
ISI Accession Number ID
WOS:000077480300042
References
References in Scopus

 

DC FieldValueLanguage
dc.contributor.authorSy, LKen_HK
dc.contributor.authorBrown, GDen_HK
dc.date.accessioned2010-09-06T06:13:55Z-
dc.date.available2010-09-06T06:13:55Z-
dc.date.issued1998en_HK
dc.identifier.citationPhytochemistry, 1998, v. 49 n. 6, p. 1741-1744en_HK
dc.identifier.issn0031-9422en_HK
dc.identifier.urihttp://hdl.handle.net/10722/69467-
dc.description.abstractThe absolute stereochemistry of the epoxide group in alpinia epoxide [14,15-epoxylabda-8(17),12-dien-16-al (E)] has been determined by simultaneous reduction of the aldehyde and epoxide functional groups in this molecule to primary and secondary alcohols, followed by selective protection of the primary alcohol and derivitization of the secondary alcohol with S(+) and R(-) MTPCl as Mosher esters. Changes in 1H NMR chemical shifts for all positions in these two esters were determined by 2D-NMR and used to infer the absolute stereochemistry of the epoxide group in the natural product alpinia epoxide.en_HK
dc.languageengen_HK
dc.publisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/phytochemen_HK
dc.relation.ispartofPhytochemistryen_HK
dc.subject14,15-epoxylabda- 8(17),12-dien-16-al (E)en_HK
dc.subjectAbsolute stereochemistryen_HK
dc.subjectAlpina epoxideen_HK
dc.subjectAlpinia chinensisen_HK
dc.subjectMosher ester, two-dimensional NMRen_HK
dc.subjectS(+)/R(-) MTPClen_HK
dc.subjectZingiberaceaeen_HK
dc.titleDetermination of the absolute stereochemistry of the epoxide group in alpinia epoxide by NMRen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0031-9422&volume=49&issue=6&spage=1741&epage=1744&date=1998&atitle=Determination+of+the+absolute+stereochemistry+of+the+epoxide+group+in+alpinia+epoxide+by+NMRen_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/S0031-9422(98)00298-2en_HK
dc.identifier.scopuseid_2-s2.0-0031793738en_HK
dc.identifier.hkuros40368en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0031793738&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume49en_HK
dc.identifier.issue6en_HK
dc.identifier.spage1741en_HK
dc.identifier.epage1744en_HK
dc.identifier.isiWOS:000077480300042-
dc.publisher.placeUnited Kingdomen_HK
dc.identifier.scopusauthoridSy, LK=35874602700en_HK
dc.identifier.scopusauthoridBrown, GD=7406468149en_HK
dc.identifier.issnl0031-9422-

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