Oxidative Functionalization of Trinor-18α-olean-17(22)-ene Derivatives. Annulation of the E-Ring by an Intramolecular Aldol Reaction

[Image: see text] cis-Dihydroxylation of trinor-18α-olean-17(22)-ene 2 with osmium tetroxide led to diol 9. Its cleavage with lead tetraacetate gave tetracyclic ketoaldehyde 10. By comparison, the ozonation of trinor-18α-olean-17(22)-ene 2 in the presence of p-toluenesulfonic acid gave the correspon...

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Autores principales: Kuczynska, Kinga, Jaźwiński, Jarosław, Pakulski, Zbigniew, Cmoch, Piotr, Luboradzki, Roman
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8279477/
https://www.ncbi.nlm.nih.gov/pubmed/34033473
http://dx.doi.org/10.1021/acs.joc.1c00697
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author Kuczynska, Kinga
Jaźwiński, Jarosław
Pakulski, Zbigniew
Cmoch, Piotr
Luboradzki, Roman
author_facet Kuczynska, Kinga
Jaźwiński, Jarosław
Pakulski, Zbigniew
Cmoch, Piotr
Luboradzki, Roman
author_sort Kuczynska, Kinga
collection PubMed
description [Image: see text] cis-Dihydroxylation of trinor-18α-olean-17(22)-ene 2 with osmium tetroxide led to diol 9. Its cleavage with lead tetraacetate gave tetracyclic ketoaldehyde 10. By comparison, the ozonation of trinor-18α-olean-17(22)-ene 2 in the presence of p-toluenesulfonic acid gave the corresponding ketoacetal 12. Both products were subjected to an intramolecular aldol reaction under the acidic conditions and yielded unusual triterpenes bearing a bicyclo[4.3.1]decane fragment (22). Further manipulation of the protective groups afforded compounds useful in triterpene synthesis, especially in the preparation of potentially biologically active saponins based on a tetracyclic terpene core.
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spelling pubmed-82794772021-07-15 Oxidative Functionalization of Trinor-18α-olean-17(22)-ene Derivatives. Annulation of the E-Ring by an Intramolecular Aldol Reaction Kuczynska, Kinga Jaźwiński, Jarosław Pakulski, Zbigniew Cmoch, Piotr Luboradzki, Roman J Org Chem [Image: see text] cis-Dihydroxylation of trinor-18α-olean-17(22)-ene 2 with osmium tetroxide led to diol 9. Its cleavage with lead tetraacetate gave tetracyclic ketoaldehyde 10. By comparison, the ozonation of trinor-18α-olean-17(22)-ene 2 in the presence of p-toluenesulfonic acid gave the corresponding ketoacetal 12. Both products were subjected to an intramolecular aldol reaction under the acidic conditions and yielded unusual triterpenes bearing a bicyclo[4.3.1]decane fragment (22). Further manipulation of the protective groups afforded compounds useful in triterpene synthesis, especially in the preparation of potentially biologically active saponins based on a tetracyclic terpene core. American Chemical Society 2021-05-25 2021-06-04 /pmc/articles/PMC8279477/ /pubmed/34033473 http://dx.doi.org/10.1021/acs.joc.1c00697 Text en © 2021 The Authors. Published by American Chemical Society Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Kuczynska, Kinga
Jaźwiński, Jarosław
Pakulski, Zbigniew
Cmoch, Piotr
Luboradzki, Roman
Oxidative Functionalization of Trinor-18α-olean-17(22)-ene Derivatives. Annulation of the E-Ring by an Intramolecular Aldol Reaction
title Oxidative Functionalization of Trinor-18α-olean-17(22)-ene Derivatives. Annulation of the E-Ring by an Intramolecular Aldol Reaction
title_full Oxidative Functionalization of Trinor-18α-olean-17(22)-ene Derivatives. Annulation of the E-Ring by an Intramolecular Aldol Reaction
title_fullStr Oxidative Functionalization of Trinor-18α-olean-17(22)-ene Derivatives. Annulation of the E-Ring by an Intramolecular Aldol Reaction
title_full_unstemmed Oxidative Functionalization of Trinor-18α-olean-17(22)-ene Derivatives. Annulation of the E-Ring by an Intramolecular Aldol Reaction
title_short Oxidative Functionalization of Trinor-18α-olean-17(22)-ene Derivatives. Annulation of the E-Ring by an Intramolecular Aldol Reaction
title_sort oxidative functionalization of trinor-18α-olean-17(22)-ene derivatives. annulation of the e-ring by an intramolecular aldol reaction
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8279477/
https://www.ncbi.nlm.nih.gov/pubmed/34033473
http://dx.doi.org/10.1021/acs.joc.1c00697
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