Synthesis and determination of the absolute configuration of (-)-(5R,6Z)-dendrolasin-5-acetate from the nudibranch Hypselodoris jacksoni.
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.
School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane QLD 4072, Australia.
I Wayan
IW
Mudianta
School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane QLD 4072, Australia.
Victoria L
VL
Challinor
School of Biological Sciences, The University of Queensland, Brisbane QLD 4072, Australia.
Anne E
AE
Winters
School of Biological Sciences, The University of Queensland, Brisbane QLD 4072, Australia.
Karen L
KL
Cheney
School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane QLD 4072, Australia.
James J
JJ
De Voss
School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane QLD 4072, Australia.
Mary J
MJ
Garson
E/Z-isomers; Hypselodoris; enantioselective HPLC; natural products; nudibranch; sesquiterpene