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

I. Wayan Mudianta, Victoria Louise Challinor, Anne E. Winters, Karen L. Cheney, James J. De Voss, Mary J. Garson

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8 Citationer (Scopus)

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.

OriginalsprogEngelsk
TidsskriftBeilstein Journal of Organic Chemistry
Vol/bind9
Sider (fra-til)2925-2933
Antal sider9
ISSN2195-951X
DOI
StatusUdgivet - 2013
Udgivet eksterntJa

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