Structural revision of Stemoburkilline from an E-alkene to a Z-alkene

Sastraruji, K; Pyne, SG; Ung, AT; Mungkornasawakul, P; Lie, W; Jatisatienr, A

Structural revision of Stemoburkilline from an E-alkene to a Z-alkene

Sastraruji, K Pyne, SG Ung, AT

Mungkornasawakul, P Lie, W Jatisatienr, A

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Publication Type:: Journal Article
Citation:: Journal of Natural Products, 2009, 72 (2), pp. 316 - 318
Issue Date:: 2009-02-01

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Field	Value	Language
dc.contributor.author	Sastraruji, K	en_US
dc.contributor.author	Pyne, SG	en_US
dc.contributor.author	Ung, AT https://orcid.org/0000-0002-5665-0702	en_US
dc.contributor.author	Mungkornasawakul, P	en_US
dc.contributor.author	Lie, W	en_US
dc.contributor.author	Jatisatienr, A	en_US
dc.date.issued	2009-02-01	en_US
dc.identifier.citation	Journal of Natural Products, 2009, 72 (2), pp. 316 - 318	en_US
dc.identifier.issn	0163-3864	en_US
dc.identifier.uri	http://hdl.handle.net/10453/11789
dc.description.abstract	Semisynthesis studies starting from (11Z)-1′,2′- didehydrostemofoline (4) indicated that the known Stemona alkaloid stemoburkilline is the Z-isomer and not the E-isomer as initially reported. The semisynthesis involved conversion of (11Z)-1′,2′- didehydrostemofoline (4) to 11(S),12(S)-dihydrostemofoline (3) followed by a stereoselective base-catalyzed ring-opening reaction to give (Z)-stemoburkilline (8). The same product was obtained using a similar synthetic protocol starting from isostemofoline (6) via a based-catalyzed ring-opening reaction of 11(S),12(R)-dihydrostemofoline (1). A re-examination of the crude root extracts of Stemona burkillii Prain and further NOE studies established stemoburkilline as the Z-isomer (8). © 2009 American Chemical Society and American Society of Pharmacognosy.	en_US
dc.relation.ispartof	Journal of Natural Products	en_US
dc.relation.isbasedon	10.1021/np800755p	en_US
dc.subject.classification	Medicinal & Biomolecular Chemistry	en_US
dc.subject.mesh	Stemonaceae	en_US
dc.subject.mesh	Alkenes	en_US
dc.subject.mesh	Alkaloids	en_US
dc.subject.mesh	Furans	en_US
dc.subject.mesh	Heterocyclic Compounds, 4 or More Rings	en_US
dc.subject.mesh	Molecular Structure	en_US
dc.subject.mesh	Stereoisomerism	en_US
dc.title	Structural revision of Stemoburkilline from an E-alkene to a Z-alkene	en_US
dc.type	Journal Article
utslib.citation.volume	2	en_US
utslib.citation.volume	72	en_US
utslib.for	060702 Plant Cell and Molecular Biology	en_US
utslib.for	03 Chemical Sciences	en_US
utslib.for	06 Biological Sciences	en_US
utslib.for	11 Medical and Health Sciences	en_US
pubs.embargo.period	Not known	en_US
pubs.organisational-group	/University of Technology Sydney
pubs.organisational-group	/University of Technology Sydney/Faculty of Science
pubs.organisational-group	/University of Technology Sydney/Faculty of Science/School of Mathematical and Physical Sciences
pubs.organisational-group	/University of Technology Sydney/Strength - CCET - Centre for Clean Energy Technology
utslib.copyright.status	closed_access
pubs.issue	2	en_US
pubs.publication-status	Published	en_US
pubs.volume	72	en_US

Abstract:

Semisynthesis studies starting from (11Z)-1′,2′- didehydrostemofoline (4) indicated that the known Stemona alkaloid stemoburkilline is the Z-isomer and not the E-isomer as initially reported. The semisynthesis involved conversion of (11Z)-1′,2′- didehydrostemofoline (4) to 11(S),12(S)-dihydrostemofoline (3) followed by a stereoselective base-catalyzed ring-opening reaction to give (Z)-stemoburkilline (8). The same product was obtained using a similar synthetic protocol starting from isostemofoline (6) via a based-catalyzed ring-opening reaction of 11(S),12(R)-dihydrostemofoline (1). A re-examination of the crude root extracts of Stemona burkillii Prain and further NOE studies established stemoburkilline as the Z-isomer (8). © 2009 American Chemical Society and American Society of Pharmacognosy.

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http://hdl.handle.net/10453/11789