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 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.

Automated summary

Simmons-Smith cyclopropanation is a widely used reaction in organic synthesis for the conversion of alkenes into cyclopropane. It is an important reaction because cyclopropane is a key intermediate in the synthesis of biologically active natural compounds. The modified form of this reaction using Et2Zn and CH2I2 has been successfully applied in the total synthesis of complex natural products with diverse biological activities. This review provides an overview of the Furukawa-modified Simmons-Smith cyclopropanation from 2005 to 2022.