Synthesis and determination of the absolute configuration of (-)-(5R,6Z)-dendrolasin-5-acetate from the nudibranch Hypselodoris jacksoni

Mudianta, I. Wayan, Challinor, Victoria L., Winters, Anne E., Cheney, Karen L., De Voss, James J. and Garson, Mary J. (2013) Synthesis and determination of the absolute configuration of (-)-(5R,6Z)-dendrolasin-5-acetate from the nudibranch Hypselodoris jacksoni. Beilstein Journal of Organic Chemistry, 9 2925-2933. doi:10.3762/bjoc.9.329


Author Mudianta, I. Wayan
Challinor, Victoria L.
Winters, Anne E.
Cheney, Karen L.
De Voss, James J.
Garson, Mary J.
Title Synthesis and determination of the absolute configuration of (-)-(5R,6Z)-dendrolasin-5-acetate from the nudibranch Hypselodoris jacksoni
Formatted title
Synthesis and determination of the absolute configuration of (-)-(5R,6Z)-dendrolasin-5-acetate from the nudibranch Hypselodoris jacksoni 
Journal name Beilstein Journal of Organic Chemistry   Check publisher's open access policy
ISSN 1860-5397
Publication date 2013-12-23
Sub-type Article (original research)
DOI 10.3762/bjoc.9.329
Open Access Status DOI
Volume 9
Start page 2925
End page 2933
Total pages 9
Place of publication Frankfurt am Main, Germany
Publisher Beilstein - Institut zur Foerderung der Chemischen Wissenschaften
Collection year 2014
Language eng
Formatted abstract
A small sample of (-)-(5R,6Z)-dendrolasin-5-acetate, which was fully characterized by 2D NMR studies, was isolated from the nudibranch Hypselodoris jacksoni, along with the sesquiterpenes (+)-agassizin, (-)-furodysinin, (-)-euryfuran, (-)-dehydroherbadysidolide and (+)-pallescensone. A synthetic sample ([α]D -8.7) of the new metabolite was prepared by [1,2]-Wittig rearrangement of a geranylfuryl ether followed by acetylation of purified alcohol isomers. The absolute configuration at C-5 was established as R by the analysis of MPA ester derivatives of (Z)-5-hydroxydendrolasin obtained by preparative enantioselective HPLC.
Keyword E/Z-isomers
Enantioselective HPLC
Hypselodoris
Natural products
Nudibranch
Sesquiterpene
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2014 Collection
School of Biological Sciences Publications
School of Chemistry and Molecular Biosciences
 
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