Isolation of a Bis-Iodurated Tetra-THF as a Trace Product from the Oxidation of Squalene with RuO(4) and Its Double Ring Expansion to a Novel bis-THF-bis-THP Compound

A novel bis-iodurated polyether compound, based on an unprecedented tetra-THF backbone, has been isolated as a trace by-product of the oxidation of squalene with the catalytic system RuO(2)(cat.)/NaIO(4). The double erythro configuration of the central portion of the molecule furnishes the first ind...

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Autores principales: Piccialli, Vincenzo, Zaccaria, Sabrina, Centore, Roberto, Tuzi, Angela, Borbone, Nicola, Oliviero, Giorgia
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2011
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6264591/
https://www.ncbi.nlm.nih.gov/pubmed/21709619
http://dx.doi.org/10.3390/molecules16075362
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author Piccialli, Vincenzo
Zaccaria, Sabrina
Centore, Roberto
Tuzi, Angela
Borbone, Nicola
Oliviero, Giorgia
author_facet Piccialli, Vincenzo
Zaccaria, Sabrina
Centore, Roberto
Tuzi, Angela
Borbone, Nicola
Oliviero, Giorgia
author_sort Piccialli, Vincenzo
collection PubMed
description A novel bis-iodurated polyether compound, based on an unprecedented tetra-THF backbone, has been isolated as a trace by-product of the oxidation of squalene with the catalytic system RuO(2)(cat.)/NaIO(4). The double erythro configuration of the central portion of the molecule furnishes the first indirect support of the previously postulated pathway operating in the oxidative pentacyclization of the isoprenoid substrate. A bidirectional double oxidative bis-cyclization is invoked to explain the formation of this compound. The isolated substance was successfully subjected to a double rearrangement-ring expansion to give a novel bis-THF-bis-THP compound.
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spelling pubmed-62645912018-12-10 Isolation of a Bis-Iodurated Tetra-THF as a Trace Product from the Oxidation of Squalene with RuO(4) and Its Double Ring Expansion to a Novel bis-THF-bis-THP Compound Piccialli, Vincenzo Zaccaria, Sabrina Centore, Roberto Tuzi, Angela Borbone, Nicola Oliviero, Giorgia Molecules Article A novel bis-iodurated polyether compound, based on an unprecedented tetra-THF backbone, has been isolated as a trace by-product of the oxidation of squalene with the catalytic system RuO(2)(cat.)/NaIO(4). The double erythro configuration of the central portion of the molecule furnishes the first indirect support of the previously postulated pathway operating in the oxidative pentacyclization of the isoprenoid substrate. A bidirectional double oxidative bis-cyclization is invoked to explain the formation of this compound. The isolated substance was successfully subjected to a double rearrangement-ring expansion to give a novel bis-THF-bis-THP compound. MDPI 2011-06-27 /pmc/articles/PMC6264591/ /pubmed/21709619 http://dx.doi.org/10.3390/molecules16075362 Text en © 2011 by the authors; licensee MDPI, Basel, Switzerland. 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
Piccialli, Vincenzo
Zaccaria, Sabrina
Centore, Roberto
Tuzi, Angela
Borbone, Nicola
Oliviero, Giorgia
Isolation of a Bis-Iodurated Tetra-THF as a Trace Product from the Oxidation of Squalene with RuO(4) and Its Double Ring Expansion to a Novel bis-THF-bis-THP Compound
title Isolation of a Bis-Iodurated Tetra-THF as a Trace Product from the Oxidation of Squalene with RuO(4) and Its Double Ring Expansion to a Novel bis-THF-bis-THP Compound
title_full Isolation of a Bis-Iodurated Tetra-THF as a Trace Product from the Oxidation of Squalene with RuO(4) and Its Double Ring Expansion to a Novel bis-THF-bis-THP Compound
title_fullStr Isolation of a Bis-Iodurated Tetra-THF as a Trace Product from the Oxidation of Squalene with RuO(4) and Its Double Ring Expansion to a Novel bis-THF-bis-THP Compound
title_full_unstemmed Isolation of a Bis-Iodurated Tetra-THF as a Trace Product from the Oxidation of Squalene with RuO(4) and Its Double Ring Expansion to a Novel bis-THF-bis-THP Compound
title_short Isolation of a Bis-Iodurated Tetra-THF as a Trace Product from the Oxidation of Squalene with RuO(4) and Its Double Ring Expansion to a Novel bis-THF-bis-THP Compound
title_sort isolation of a bis-iodurated tetra-thf as a trace product from the oxidation of squalene with ruo(4) and its double ring expansion to a novel bis-thf-bis-thp compound
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6264591/
https://www.ncbi.nlm.nih.gov/pubmed/21709619
http://dx.doi.org/10.3390/molecules16075362
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