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Highly Efficient and Mild Gold (I) Catalyzed Synthesis of 3,8-Diarylidene-2,7-dioxaspiro[4.4]nonane-1,6-diones
The gold-catalyzed cyclization of 2,2-bis(3-arylprop-2-yn1-yl)malonic acid has been proposed as an efficient approach to substituted 3,8-dibenzyl-2,7-dioxaspiro[4.4]nonane-1,6-diones. The reaction proceeds smoothly in mild reaction conditions to give the desired products in quantitative yields in th...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9822471/ https://www.ncbi.nlm.nih.gov/pubmed/36615493 http://dx.doi.org/10.3390/molecules28010300 |
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author | Iazzetti, Antonia Allevi, Dario Calcaterra, Andrea Fabrizi, Giancarlo Goggiamani, Antonella Mazzoccanti, Giulia Sferrazza, Alessio Verdiglione, Rosanna Vergine, Valeria |
author_facet | Iazzetti, Antonia Allevi, Dario Calcaterra, Andrea Fabrizi, Giancarlo Goggiamani, Antonella Mazzoccanti, Giulia Sferrazza, Alessio Verdiglione, Rosanna Vergine, Valeria |
author_sort | Iazzetti, Antonia |
collection | PubMed |
description | The gold-catalyzed cyclization of 2,2-bis(3-arylprop-2-yn1-yl)malonic acid has been proposed as an efficient approach to substituted 3,8-dibenzyl-2,7-dioxaspiro[4.4]nonane-1,6-diones. The reaction proceeds smoothly in mild reaction conditions to give the desired products in quantitative yields in the presence of variously substituted starting materials. In addition, the synthesis of γ-arylidene spirobislactone bearing different substituents on the two aromatic rings has been achieved. This kind of compound could be of great interest in pharmaceutical science given the widespread presence of this scaffold in bioactive natural and synthetic products. |
format | Online Article Text |
id | pubmed-9822471 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-98224712023-01-07 Highly Efficient and Mild Gold (I) Catalyzed Synthesis of 3,8-Diarylidene-2,7-dioxaspiro[4.4]nonane-1,6-diones Iazzetti, Antonia Allevi, Dario Calcaterra, Andrea Fabrizi, Giancarlo Goggiamani, Antonella Mazzoccanti, Giulia Sferrazza, Alessio Verdiglione, Rosanna Vergine, Valeria Molecules Article The gold-catalyzed cyclization of 2,2-bis(3-arylprop-2-yn1-yl)malonic acid has been proposed as an efficient approach to substituted 3,8-dibenzyl-2,7-dioxaspiro[4.4]nonane-1,6-diones. The reaction proceeds smoothly in mild reaction conditions to give the desired products in quantitative yields in the presence of variously substituted starting materials. In addition, the synthesis of γ-arylidene spirobislactone bearing different substituents on the two aromatic rings has been achieved. This kind of compound could be of great interest in pharmaceutical science given the widespread presence of this scaffold in bioactive natural and synthetic products. MDPI 2022-12-30 /pmc/articles/PMC9822471/ /pubmed/36615493 http://dx.doi.org/10.3390/molecules28010300 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Iazzetti, Antonia Allevi, Dario Calcaterra, Andrea Fabrizi, Giancarlo Goggiamani, Antonella Mazzoccanti, Giulia Sferrazza, Alessio Verdiglione, Rosanna Vergine, Valeria Highly Efficient and Mild Gold (I) Catalyzed Synthesis of 3,8-Diarylidene-2,7-dioxaspiro[4.4]nonane-1,6-diones |
title | Highly Efficient and Mild Gold (I) Catalyzed Synthesis of 3,8-Diarylidene-2,7-dioxaspiro[4.4]nonane-1,6-diones |
title_full | Highly Efficient and Mild Gold (I) Catalyzed Synthesis of 3,8-Diarylidene-2,7-dioxaspiro[4.4]nonane-1,6-diones |
title_fullStr | Highly Efficient and Mild Gold (I) Catalyzed Synthesis of 3,8-Diarylidene-2,7-dioxaspiro[4.4]nonane-1,6-diones |
title_full_unstemmed | Highly Efficient and Mild Gold (I) Catalyzed Synthesis of 3,8-Diarylidene-2,7-dioxaspiro[4.4]nonane-1,6-diones |
title_short | Highly Efficient and Mild Gold (I) Catalyzed Synthesis of 3,8-Diarylidene-2,7-dioxaspiro[4.4]nonane-1,6-diones |
title_sort | highly efficient and mild gold (i) catalyzed synthesis of 3,8-diarylidene-2,7-dioxaspiro[4.4]nonane-1,6-diones |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9822471/ https://www.ncbi.nlm.nih.gov/pubmed/36615493 http://dx.doi.org/10.3390/molecules28010300 |
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