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

Ramsha Munir; Ameer Fawad Zahoor; Sadia Javed; Bushra Parveen; Asim Mansha; Ahmad Irfan; Samreen Gul Khan; Ali Irfan; Katarzyna Kotwica-Mojzych; Mariusz Mojzych

doi:10.3390/molecules28155651

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

Molecules. 2023 Jul 26;28(15):5651. doi: 10.3390/molecules28155651.

Authors

Affiliations

¹ Medicinal Chemistry Research Lab, Department of Chemistry, Government College University Faisalabad, Faisalabad 38000, Pakistan.
² Department of Biochemistry, Government College University Faisalabad, Faisalabad 38000, Pakistan.
³ Department of Chemistry, College of Science, King Khalid University, Abha 61413, Saudi Arabia.
⁴ Laboratory of Experimental Cytology, Medical University of Lublin, Radziwiłłowska 11, 20-080 Lublin, Poland.
⁵ Department of Chemistry, Siedlce University of Natural Sciences and Humanities, 3-go Maja 54, 08-110 Siedlce, Poland.

Abstract

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 Et₂Zn and CH₂I₂ (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.

Keywords: Furukawa reagent; Simmons–Smith cyclopropanation; drugs; natural products.

Publication types

Review

MeSH terms

Alkaloids* / chemistry
Biological Products* / chemistry
Cyclization
Cyclopropanes / chemistry
Nucleosides

Substances

Biological Products
Alkaloids
Nucleosides
cyclopropane
Cyclopropanes

Grants and funding

The research was partly financed by research projects: Siedlce University of Natural Sciences and Humanities (UPH/WNSP/ICH/zadaniebadawcze/143/23/B), Medical University of Lublin (DS 730).