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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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Detalles Bibliográficos
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
Descripción
Sumario: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.