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

被引：9

作者：

Munir, Ramsha ^{[1
]}

Zahoor, Ameer Fawad ^{[1
]}

Javed, Sadia ^{[2
]}

Parveen, Bushra ^{[1
]}

Mansha, Asim ^{[1
]}

Irfan, Ahmad ^{[3
]}

Khan, Samreen Gul ^{[1
]}

Irfan, Ali ^{[1
]}

Kotwica-Mojzych, Katarzyna ^{[4
]}

Mojzych, Mariusz ^{[5
]}

机构：

[1] Govt Coll Univ Faisalabad, Dept Chem, Med Chem Res Lab, Faisalabad 38000, Pakistan

[2] Govt Coll Univ Faisalabad, Dept Biochem, Faisalabad 38000, Pakistan

[3] King Khalid Univ, Coll Sci, Dept Chem, Abha 61413, Saudi Arabia

[4] Med Univ Lublin, Lab Expt Cytol, Radziwillowska 11, PL-20080 Lublin, Poland

[5] Siedlce Univ Nat Sci & Humanities, Dept Chem, 3-go Maja 54, PL-08110 Siedlce, Poland

来源：

MOLECULES | 2023年 / 28卷 / 15期

关键词：

Simmons-Smith cyclopropanation; natural products; drugs; Furukawa reagent; PLANT-GROWTH PROMOTERS; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; NUCLEOSIDE ANALOGS; SOLANDELACTONES-A; INDOLE ALKALOIDS; TERPENDOLE-E; HEPATITIS-C; DERIVATIVES; ALCOHOLS;

D O I：

10.3390/molecules28155651

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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.

引用

页数：50

共 19 条

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ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (16) : 3331 - 3337
[2] Zeolite Catalytic Simmons-Smith Cyclopropanation of Alkenes for the Synthesis of High-Energy-Density Fuels
Liu, Yakun
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Shi, Chengxiang
Pan, Lun
Zhang, Xiangwen
Zou, Ji-Jun
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2024, 63 (16) : 6985 - 6994
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JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (25): : 8628 - 8629
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MAJERSKI, Z
SCHLEYER, PV
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (10): : 3215 - +
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Du, Haifeng
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ORGANIC LETTERS, 2006, 8 (13) : 2827 - 2829
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CHEMICAL ENGINEERING SCIENCE, 2024, 283
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Cheng, D
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ORGANIC LETTERS, 2001, 3 (13) : 2121 - 2123
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Bull, James A.
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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (06) : 1895 - 1902
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ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (18) : 3082 - 3087
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SYNTHETIC COMMUNICATIONS, 2017, 47 (12) : 1121 - 1135

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