Total Synthesis and Absolute Configuration of the Marine Norditerpenoid Xestenone

Xestenone is a marine norditerpenoid found in the northeastern Pacific sponge Xestospongia vanilla. The relative configuration of C-3 and C-7 in xestenone was determined by NOESY spectral analysis. However the relative configuration of C-12 and the absolute configuration of this compound were not de...

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Autores principales: Ota, Koichiro, Kurokawa, Takao, Kawashima, Etsuko, Miyaoka, Hiroaki
Formato: Texto
Lenguaje:English
Publicado: Molecular Diversity Preservation International 2009
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2810225/
https://www.ncbi.nlm.nih.gov/pubmed/20098605
http://dx.doi.org/10.3390/md7040654
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author Ota, Koichiro
Kurokawa, Takao
Kawashima, Etsuko
Miyaoka, Hiroaki
author_facet Ota, Koichiro
Kurokawa, Takao
Kawashima, Etsuko
Miyaoka, Hiroaki
author_sort Ota, Koichiro
collection PubMed
description Xestenone is a marine norditerpenoid found in the northeastern Pacific sponge Xestospongia vanilla. The relative configuration of C-3 and C-7 in xestenone was determined by NOESY spectral analysis. However the relative configuration of C-12 and the absolute configuration of this compound were not determined. The authors have now achieved the total synthesis of xestenone using their developed one-pot synthesis of cyclopentane derivatives employing allyl phenyl sulfone and an epoxy iodide as a key step. The relative and absolute configurations of xestenone were thus successfully determined by this synthesis.
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spelling pubmed-28102252010-01-22 Total Synthesis and Absolute Configuration of the Marine Norditerpenoid Xestenone Ota, Koichiro Kurokawa, Takao Kawashima, Etsuko Miyaoka, Hiroaki Mar Drugs Article Xestenone is a marine norditerpenoid found in the northeastern Pacific sponge Xestospongia vanilla. The relative configuration of C-3 and C-7 in xestenone was determined by NOESY spectral analysis. However the relative configuration of C-12 and the absolute configuration of this compound were not determined. The authors have now achieved the total synthesis of xestenone using their developed one-pot synthesis of cyclopentane derivatives employing allyl phenyl sulfone and an epoxy iodide as a key step. The relative and absolute configurations of xestenone were thus successfully determined by this synthesis. Molecular Diversity Preservation International 2009-11-24 /pmc/articles/PMC2810225/ /pubmed/20098605 http://dx.doi.org/10.3390/md7040654 Text en © 2009 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland http://creativecommons.org/licenses/by/3.0 This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Ota, Koichiro
Kurokawa, Takao
Kawashima, Etsuko
Miyaoka, Hiroaki
Total Synthesis and Absolute Configuration of the Marine Norditerpenoid Xestenone
title Total Synthesis and Absolute Configuration of the Marine Norditerpenoid Xestenone
title_full Total Synthesis and Absolute Configuration of the Marine Norditerpenoid Xestenone
title_fullStr Total Synthesis and Absolute Configuration of the Marine Norditerpenoid Xestenone
title_full_unstemmed Total Synthesis and Absolute Configuration of the Marine Norditerpenoid Xestenone
title_short Total Synthesis and Absolute Configuration of the Marine Norditerpenoid Xestenone
title_sort total synthesis and absolute configuration of the marine norditerpenoid xestenone
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2810225/
https://www.ncbi.nlm.nih.gov/pubmed/20098605
http://dx.doi.org/10.3390/md7040654
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AT kawashimaetsuko totalsynthesisandabsoluteconfigurationofthemarinenorditerpenoidxestenone
AT miyaokahiroaki totalsynthesisandabsoluteconfigurationofthemarinenorditerpenoidxestenone

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