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Simmons–Smith Cyclopropanation: A Multifaceted Synthetic Protocol toward the Synthesis of Natural Products and Drugs: A Review

Simmons–Smith cyclopropanation is a widely used reaction in organic synthesis for stereospecific conversion of alkenes into cyclopropane. The utility of this reaction can be realized by the fact that the cyclopropane motif is a privileged synthetic intermediate and a core structural unit of many bio...

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Autores principales: Munir, Ramsha, Zahoor, Ameer Fawad, Javed, Sadia, Parveen, Bushra, Mansha, Asim, Irfan, Ahmad, Khan, Samreen Gul, Irfan, Ali, Kotwica-Mojzych, Katarzyna, Mojzych, Mariusz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10420228/
https://www.ncbi.nlm.nih.gov/pubmed/37570621
http://dx.doi.org/10.3390/molecules28155651
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author Munir, Ramsha
Zahoor, Ameer Fawad
Javed, Sadia
Parveen, Bushra
Mansha, Asim
Irfan, Ahmad
Khan, Samreen Gul
Irfan, Ali
Kotwica-Mojzych, Katarzyna
Mojzych, Mariusz
author_facet Munir, Ramsha
Zahoor, Ameer Fawad
Javed, Sadia
Parveen, Bushra
Mansha, Asim
Irfan, Ahmad
Khan, Samreen Gul
Irfan, Ali
Kotwica-Mojzych, Katarzyna
Mojzych, Mariusz
author_sort Munir, Ramsha
collection PubMed
description Simmons–Smith cyclopropanation is a widely used reaction in organic synthesis for stereospecific conversion of alkenes into cyclopropane. The utility of this reaction can be realized by the fact that the cyclopropane motif is a privileged synthetic intermediate and a core structural unit of many biologically active natural compounds such as terpenoids, alkaloids, nucleosides, amino acids, fatty acids, polyketides and drugs. The modified form of Simmons–Smith cyclopropanation involves the employment of Et(2)Zn and CH(2)I(2) (Furukawa reagent) toward the total synthesis of a variety of structurally complex natural products that possess broad range of biological activities including anticancer, antimicrobial and antiviral activities. This review aims to provide an intriguing glimpse of the Furukawa-modified Simmons–Smith cyclopropanation, within the year range of 2005 to 2022.
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spelling pubmed-104202282023-08-12 Simmons–Smith Cyclopropanation: A Multifaceted Synthetic Protocol toward the Synthesis of Natural Products and Drugs: A Review Munir, Ramsha Zahoor, Ameer Fawad Javed, Sadia Parveen, Bushra Mansha, Asim Irfan, Ahmad Khan, Samreen Gul Irfan, Ali Kotwica-Mojzych, Katarzyna Mojzych, Mariusz Molecules Review Simmons–Smith cyclopropanation is a widely used reaction in organic synthesis for stereospecific conversion of alkenes into cyclopropane. The utility of this reaction can be realized by the fact that the cyclopropane motif is a privileged synthetic intermediate and a core structural unit of many biologically active natural compounds such as terpenoids, alkaloids, nucleosides, amino acids, fatty acids, polyketides and drugs. The modified form of Simmons–Smith cyclopropanation involves the employment of Et(2)Zn and CH(2)I(2) (Furukawa reagent) toward the total synthesis of a variety of structurally complex natural products that possess broad range of biological activities including anticancer, antimicrobial and antiviral activities. This review aims to provide an intriguing glimpse of the Furukawa-modified Simmons–Smith cyclopropanation, within the year range of 2005 to 2022. MDPI 2023-07-26 /pmc/articles/PMC10420228/ /pubmed/37570621 http://dx.doi.org/10.3390/molecules28155651 Text en © 2023 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 Review
Munir, Ramsha
Zahoor, Ameer Fawad
Javed, Sadia
Parveen, Bushra
Mansha, Asim
Irfan, Ahmad
Khan, Samreen Gul
Irfan, Ali
Kotwica-Mojzych, Katarzyna
Mojzych, Mariusz
Simmons–Smith Cyclopropanation: A Multifaceted Synthetic Protocol toward the Synthesis of Natural Products and Drugs: A Review
title Simmons–Smith Cyclopropanation: A Multifaceted Synthetic Protocol toward the Synthesis of Natural Products and Drugs: A Review
title_full Simmons–Smith Cyclopropanation: A Multifaceted Synthetic Protocol toward the Synthesis of Natural Products and Drugs: A Review
title_fullStr Simmons–Smith Cyclopropanation: A Multifaceted Synthetic Protocol toward the Synthesis of Natural Products and Drugs: A Review
title_full_unstemmed Simmons–Smith Cyclopropanation: A Multifaceted Synthetic Protocol toward the Synthesis of Natural Products and Drugs: A Review
title_short Simmons–Smith Cyclopropanation: A Multifaceted Synthetic Protocol toward the Synthesis of Natural Products and Drugs: A Review
title_sort simmons–smith cyclopropanation: a multifaceted synthetic protocol toward the synthesis of natural products and drugs: a review
topic Review
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10420228/
https://www.ncbi.nlm.nih.gov/pubmed/37570621
http://dx.doi.org/10.3390/molecules28155651
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