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 sam...

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Autores principales: Mudianta, I Wayan, Challinor, Victoria L, Winters, Anne E, Cheney, Karen L, De Voss, James J, Garson, Mary J
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3896254/
https://www.ncbi.nlm.nih.gov/pubmed/24454572
http://dx.doi.org/10.3762/bjoc.9.329
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author Mudianta, I Wayan
Challinor, Victoria L
Winters, Anne E
Cheney, Karen L
De Voss, James J
Garson, Mary J
author_facet Mudianta, I Wayan
Challinor, Victoria L
Winters, Anne E
Cheney, Karen L
De Voss, James J
Garson, Mary J
author_sort Mudianta, I Wayan
collection PubMed
description 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.
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spelling pubmed-38962542014-01-21 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 Garson, Mary J Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2013-12-23 /pmc/articles/PMC3896254/ /pubmed/24454572 http://dx.doi.org/10.3762/bjoc.9.329 Text en Copyright © 2013, Mudianta et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Mudianta, I Wayan
Challinor, Victoria L
Winters, Anne E
Cheney, Karen L
De Voss, James J
Garson, Mary J
Synthesis and determination of the absolute configuration of (−)-(5R,6Z)-dendrolasin-5-acetate from the nudibranch Hypselodoris jacksoni
title Synthesis and determination of the absolute configuration of (−)-(5R,6Z)-dendrolasin-5-acetate from the nudibranch Hypselodoris jacksoni
title_full Synthesis and determination of the absolute configuration of (−)-(5R,6Z)-dendrolasin-5-acetate from the nudibranch Hypselodoris jacksoni
title_fullStr Synthesis and determination of the absolute configuration of (−)-(5R,6Z)-dendrolasin-5-acetate from the nudibranch Hypselodoris jacksoni
title_full_unstemmed Synthesis and determination of the absolute configuration of (−)-(5R,6Z)-dendrolasin-5-acetate from the nudibranch Hypselodoris jacksoni
title_short Synthesis and determination of the absolute configuration of (−)-(5R,6Z)-dendrolasin-5-acetate from the nudibranch Hypselodoris jacksoni
title_sort synthesis and determination of the absolute configuration of (−)-(5r,6z)-dendrolasin-5-acetate from the nudibranch hypselodoris jacksoni
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3896254/
https://www.ncbi.nlm.nih.gov/pubmed/24454572
http://dx.doi.org/10.3762/bjoc.9.329
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