A Short Route to the Ester (±) HomoSarkomycin via Johnson-Claisen Rearrangement

BACKGROUND: α-Methylene cycloalkanones are considered of interest because of their biological activity. Herein, in this paper the synthesis of (±) HomoSarkomycine Esters was described and characterized. METHODS: Using Bylis-Hillman adducts, triethlorthoacetate and propanoic acid, (±) HomoSarkomycine...

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Autores principales: Saied, M, Gatri, Rafik, Al-Ayed, Abdullah Sulaiman, Arfaoui, Youssef, El Gaied, Mohamed Moncef
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Bentham Science Publishers 2017
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5759048/
https://www.ncbi.nlm.nih.gov/pubmed/29399007
http://dx.doi.org/10.2174/1570178614666161230123513
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author Saied, M
Gatri, Rafik
Al-Ayed, Abdullah Sulaiman
Arfaoui, Youssef
El Gaied, Mohamed Moncef
author_facet Saied, M
Gatri, Rafik
Al-Ayed, Abdullah Sulaiman
Arfaoui, Youssef
El Gaied, Mohamed Moncef
author_sort Saied, M
collection PubMed
description BACKGROUND: α-Methylene cycloalkanones are considered of interest because of their biological activity. Herein, in this paper the synthesis of (±) HomoSarkomycine Esters was described and characterized. METHODS: Using Bylis-Hillman adducts, triethlorthoacetate and propanoic acid, (±) HomoSarkomycine Esters could be synthesized by smoothly Johnson-Claisen rearrangement. RESULTS: A small library of target compounds was prepared under optimized reaction conditions in moderate yields. The reaction mechanism and the DFT study have been investigated. CONCLUSION: This methodology provides ready access to 2-hydroxymethyl-2-cyclopentenone 1a which can be served as the raw materials of the synthesis of (±) HomoSarkomycine Ester.
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spelling pubmed-57590482018-02-02 A Short Route to the Ester (±) HomoSarkomycin via Johnson-Claisen Rearrangement Saied, M Gatri, Rafik Al-Ayed, Abdullah Sulaiman Arfaoui, Youssef El Gaied, Mohamed Moncef Lett Org Chem Article BACKGROUND: α-Methylene cycloalkanones are considered of interest because of their biological activity. Herein, in this paper the synthesis of (±) HomoSarkomycine Esters was described and characterized. METHODS: Using Bylis-Hillman adducts, triethlorthoacetate and propanoic acid, (±) HomoSarkomycine Esters could be synthesized by smoothly Johnson-Claisen rearrangement. RESULTS: A small library of target compounds was prepared under optimized reaction conditions in moderate yields. The reaction mechanism and the DFT study have been investigated. CONCLUSION: This methodology provides ready access to 2-hydroxymethyl-2-cyclopentenone 1a which can be served as the raw materials of the synthesis of (±) HomoSarkomycine Ester. Bentham Science Publishers 2017-03 2017-03 /pmc/articles/PMC5759048/ /pubmed/29399007 http://dx.doi.org/10.2174/1570178614666161230123513 Text en © 2017 Bentham Science Publishers https://creativecommons.org/licenses/by-nc/4.0/legalcode This is an open access article licensed under the terms of the Creative Commons Attribution-Non-Commercial 4.0 International Public License (CC BY-NC 4.0) (https://creativecommons.org/licenses/by-nc/4.0/legalcode), which permits unrestricted, non-commercial use, distribution and reproduction in any medium, provided the work is properly cited.
spellingShingle Article
Saied, M
Gatri, Rafik
Al-Ayed, Abdullah Sulaiman
Arfaoui, Youssef
El Gaied, Mohamed Moncef
A Short Route to the Ester (±) HomoSarkomycin via Johnson-Claisen Rearrangement
title A Short Route to the Ester (±) HomoSarkomycin via Johnson-Claisen Rearrangement
title_full A Short Route to the Ester (±) HomoSarkomycin via Johnson-Claisen Rearrangement
title_fullStr A Short Route to the Ester (±) HomoSarkomycin via Johnson-Claisen Rearrangement
title_full_unstemmed A Short Route to the Ester (±) HomoSarkomycin via Johnson-Claisen Rearrangement
title_short A Short Route to the Ester (±) HomoSarkomycin via Johnson-Claisen Rearrangement
title_sort short route to the ester (±) homosarkomycin via johnson-claisen rearrangement
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5759048/
https://www.ncbi.nlm.nih.gov/pubmed/29399007
http://dx.doi.org/10.2174/1570178614666161230123513
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