Article
Chemistry, Multidisciplinary
Ya-Ting Chang, Ling-Jun Liu, Wen-Sheng Peng, Lin-Ting Lin, Yi-Tsu Chan, Fu-Yu Tsai
Summary: Isoflavones were synthesized via Stille coupling catalyzed by a water-soluble and reusable PdCl2(NH3)(2)/2,2 '-cationic bipyridyl system in aqueous solution. The prototype 3-bromochromone required 80 degrees C for 24 hr with 2.5 mol% catalyst, while substituted 3-bromochromones needed NaHCO3 and a higher reaction temperature.
JOURNAL OF THE CHINESE CHEMICAL SOCIETY
(2021)
Article
Biochemistry & Molecular Biology
Asma Hrizi, Manon Cailler, Moufida Romdhani-Younes, Yvan Carcenac, Jerome Thibonnet
Summary: This study describes a method for the preparation of polysubstituted indole-2-carbonitriles through a cross-coupling reaction. The reactivity of indole derivatives with iodine at position 3 was studied using various cross-coupling reactions. Sonogashira, Suzuki-Miyaura, Stille, and Heck cross-couplings provided a variety of di-, tri- and tetra-substituted indole-2-carbonitriles.
Article
Chemistry, Multidisciplinary
Zhenghong Zhou, Jimin Yang, Bo Yang, Yang Han, Lijuan Zhu, Xiao-Song Xue, Feng Zhu
Summary: This study presents a pioneering example of nickel-catalysed enantioconvergent Stille cross-coupling reactions. The reactions result in the formation of C-C bonds in good to high yields with excellent stereoselectivity, providing a practical and cost-effective method for synthesis. The innovative use of synergistic photoredox/nickel catalysis enables a novel single-electron transmetalation process, opening up new research possibilities in the field of Stille reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Ganapathy Ranjani, Rajagopal Nagarajan
Summary: A novel metal-free cross-dehydrogenative coupling method was developed, leading to the synthesis of a series of specific compounds with controlled functional groups. High yields were achieved through precise control of reaction conditions, offering a new strategy in the field of organic synthesis.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Yannick Linne, Elisa Bonandi, Christopher Tabet, Jan Geldsetzer, Markus Kalesse
Summary: The first total synthesis of chondrochloren A was achieved using a 1,2-metallate rearrangement addition as an alternative to the Nozaki-Hiyama-Kishi reaction. This approach not only overcomes the challenges of the polyketide segment but also provides a novel strategy for assembling polyketidal frameworks, utilizing a Z-selective cross coupling to form the Z-enamide.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Zhiqiang Ren, Zhongliu Sun, Yifei Li, Xin Fan, Mingda Dai, Yunxia Wang, Xiangdong Hu
Summary: A new synthetic strategy was reported for the first-time asymmetric synthesis of three compounds belonging to the Cephalotaxus diterpenoids class, featuring a diastereoselective Pauson-Khand reaction and a ring-closing metathesis/elimination protocol for the core tetracyclic skeleton and tropone moiety construction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Correction
Biochemistry & Molecular Biology
Christopher J. Huck, Yaroslav D. Boyko, David Sarlah
Summary: The article is a correction regarding dearomative logic in natural product total synthesis by Christopher J. Huck et al. The authors present a new method that can be applied effectively in the synthesis of natural products and provide relevant examples.
NATURAL PRODUCT REPORTS
(2022)
Article
Chemistry, Multidisciplinary
Yota Uwabe, Kei Muto, Junichiro Yamaguchi
Summary: The total synthesis of C11-oxygenated Cephalotaxus alkaloids, fortuneicyclidins A and B, and cephalotine B was achieved by Pd-catalyzed dearomative spirocyclization of bromofurans with N-tosylhydrazones, followed by acid-mediated tandem transformation. The concise synthesis of these compounds was completed through chemo-selective and catalytic functional group conversions.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Chengsen Cui, Mingji Dai
Summary: We present a highly efficient and convergent strategy for synthesizing UCS1025A and its diastereomer tetra-epi-UCS1025A. UCS1025A is a representative member of the naturally occurring pyrrolizidinone polyketides, some of which exhibit potent antibacterial, antifungal, and anticancer activities. Our approach involves a tandem carbonylative Stille cross coupling and Diels-Alder reaction to form a key C-C bond and construct the trans-decalin system. The process uses carbon monoxide as a linchpin to connect a vinyl triflate and a vinylstannane, resulting in the desired enone moiety for subsequent intramolecular Diels-Alder cyclization. Additionally, our synthesis provides a versatile method for synthesizing other pyrrolizidinone-containing polyketides.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Fanglin Xue, Hengmao Liu, Rui Wang, Dan Zhang, Hao Song, Xiao-Yu Liu, Yong Qin
Summary: A catalytic asymmetric total synthesis of (+)-vincamine is reported, featuring a Pd-catalyzed enantioselective decarboxylative allylation and a stereoselective iminium reduction.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Yusuke Imamura, Kyohei Takaoka, Yuma Komori, Masanori Nagatomo, Masayuki Inoue
Summary: This study presents a 34-step synthesis of Taxol, involving inter- and intramolecular radical reactions to connect the A- and C-ring fragments and cyclize the B-ring. The A- and C-ring functional groups were then efficiently modified using newly developed selective reactions. The construction of the D-ring and its conjugation with the beta-amino acid led to the successful synthesis of Taxol. This synthesis provides useful insights for the design of multistep syntheses of diverse bioactive natural products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Medicinal
Yumiko Yamano, Mari Tanabe, Atsushi Shimada, Akimori Wada
Summary: The first total synthesis of loroxanthin (1) was achieved using a series of reactions, and the detailed operation methods of each reaction step were described. This synthesis method provides a basis for further research and application of loroxanthin.
Review
Chemistry, Medicinal
Aqsa Kanwal, Muhammad Bilal, Nasir Rasool, Muhammad Zubair, Syed Adnan Ali Shah, Zainul Amiruddin Zakaria
Summary: This review discusses the total synthesis, origin, and biological potential of terpenes, highlighting their wide applications in the medicinal, flavor, and fragrance industries.
Article
Chemistry, Multidisciplinary
Christopher A. Wilhelmsen, Xuntong Zhang, Jesse A. Myhill, James P. Morken
Summary: Versatile beta tert-boryl amides were synthesized through conjunctive cross-coupling of alpha-substituted alkenyl boron ate complexes and carbamoyl chloride electrophiles. The use of a palladium catalyst in combination with MandyPhos enabled enantioselective synthesis. Additionally, the chemoselectivity of the reaction product was enhanced by the addition of water.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Robert D. Hale, David M. Mcdonald, David A. Spiegel
Summary: Marine alkaloids with a diaminoimidazole-derived core have fascinating chemical structures and have shown promising antimicrobial activity. However, the synthesis of these compounds is hindered by a lack of methods to generate the densely functionalized multicyclic cores that contain a relatively large number of nitrogen atoms. In this study, a new total synthesis of the marine alkaloid (+/-)-dibromoagelaspongin is reported. The key intermediate, a 2,5-diaminoisoimidazole, is accessed in one step, bypassing the need for redox and protecting group manipulations. The natural product is obtained in fewer steps than the previous route, and with excellent overall yield.
Review
Biochemistry & Molecular Biology
Majid M. Heravi, Pourya Mohammadi
Summary: Layered double hydroxides (LDHs) are utilized as efficient and eco-friendly catalysts in Suzuki, Heck, Sonogashira, and Ullmann cross-coupling reactions, leading to carbon-carbon bond formations.
MOLECULAR DIVERSITY
(2022)
Article
Engineering, Chemical
Ghazaleh Jahani, Masoume Malmir, Majid M. Heravi
Summary: A novel nitrogen- and sulfur-doped graphene carbon dot-modified magnetic nanocomposite was synthesized and characterized. The catalyst, Fe3O4/g-CSNCDs, showed excellent catalytic activity and selectivity in alcohol oxidation. The carbonation of reagents and magnetic nanoparticles were found to have an impact on the catalytic performance. The Fe3O4/g-CSNCDs catalyst not only exhibited recyclability and magnetic recovery, but also showed improved catalytic activity compared to the bare g-CSNCDs.
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
(2022)
Review
Chemistry, Multidisciplinary
Heshmatollah Sepahvand, Majid M. Heravi, Mahyar Saber, Seyyed Emad Hooshmand
Summary: Enzymes play a key role in chemical industries as biological catalysts. Immobilization of enzymes using techniques like the Ugi multicomponent reaction can enhance their stability and activity, leading to a more robust catalyst system. Immobilized enzymes through Ugi MCR show good stability and activity, with the potential for synergistic effects on enzyme activities.
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Majid M. Heravi, Reihaneh Malakooti, Kosar Kafshdarzadeh, Zahra Amiri, Vahideh Zadsirjan, Hassan Atashin
Summary: An eco-friendly method for the synthesis of substituted dihydropyrano[2,3-c]pyrazole and benzylpyrazolyl coumarin derivatives has been developed through a multicomponent reaction. The method offers wide scope, high yields, short reaction times, and simple workup procedure. Furthermore, the nanocatalyst used in this method can be easily recovered and reused multiple times without significant loss in catalytic activity and performance.
RESEARCH ON CHEMICAL INTERMEDIATES
(2022)
Article
Chemistry, Organic
Zahra Khademi, Majid M. Heravi
Summary: The Claisen condensation is a base-mediated reaction that generates alpha,beta-keto ester by reacting an ester with a molecule containing alpha-hydrogen atom. This review focuses on the applications of Claisen condensation in the total synthesis of natural products, covering relevant literature up to the beginning of 2021.
Article
Multidisciplinary Sciences
Samahe Sadjadi, Fatemeh Koohestani, Majid M. Heravi
Summary: 1-Butyl-3-vinylimidazolium chloride was synthesized and polymerized with acrylamide to form an ionic liquid-containing polymer, which was then used to create a composite with iron-based metal-organic framework. The resulting composite exhibited high catalytic activity and recyclability for ultrasonic-assisted Knoevenagel condensation.
SCIENTIFIC REPORTS
(2022)
Review
Chemistry, Multidisciplinary
Majid M. Heravi, Vahideh Zadsirjan
Summary: This review summarizes recent advances in the synthesis and aromatization of Hantzsch 1,4-dihydropyridines under microwave irradiation, highlighting the use of this green approach.
Review
Chemistry, Applied
Yalda Rangraz, Majid M. Heravi
Summary: The development of methodologies for carbon-nitrogen bond formation is crucial in organic synthesis, as the resulting products are widely used in pharmaceuticals, biologically active compounds, and natural products. Recently, nanosized metal catalysts have gained significant attention for their excellent catalytic performance, high product yields, mild reaction conditions, and environmental sustainability. This review provides an overview of the latest progress in the fabrication of nanocatalysts and their applications in constructing carbon-nitrogen bonds via cross-coupling reactions.
APPLIED ORGANOMETALLIC CHEMISTRY
(2023)
Review
Chemistry, Organic
Majid M. Heravi, Batoul Alipour, Vahideh Zadsirjan, Masoume Malmir
Summary: The Robinson annulation is a significant reaction for the synthesis of alpha,beta-unsaturated ketone ring that involves the generation of two C-C bonds. It has been frequently used in the total synthesis of biologically active natural products. These products and their derivatives play a major role in pharmacotherapy, especially for cancer and infectious diseases.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Masoume Malmir, Majid M. Heravi, Zahra Yekke-Ghasemi, Satar Saberi, Masoud Mirzaei
Summary: A new heterogeneous catalyst, TBA8[Zr(W5O18)2]middot17H2O (Zr(W5)2), was synthesized and characterized. It was found that the catalyst had a sandwich-type structure consisting of zirconium ions and mono-lacunary Lindqvist [W5O18 ]4- anions, encapsulated by TBA+ cations. This catalyst exhibited hydrophobic properties and improved catalytic efficiency by trapping reactants on its surface. Using Zr(W5)2 as a catalyst, a series of 1,5-benzodiazepines were successfully synthesized via mild and solvent-free reactions.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Applied
Masoume Malmir, Majid M. Heravi, Ghazaleh Jahani
Summary: Metal-organic frameworks (MOFs) are viable and environmentally friendly alternatives to traditional catalysts, and the magnetic Ox-CN-Cu-MOF catalyst has shown remarkable catalytic performance due to its unique structure and Lewis acidic properties. It also exhibits excellent recyclability.
APPLIED ORGANOMETALLIC CHEMISTRY
(2023)
Article
Biotechnology & Applied Microbiology
Masoumeh Bagheri Bisafar, Masoume Malmir, Majid M. Heravi
Summary: In this study, a novel magnetic MOFs-based catalyst was synthesized and showed good catalytic activity and stability for the reduction of nitroarenes and organic dyes. The catalyst can be easily separated and recovered by magnetic separation, and it can be reused for multiple cycles.
JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY
(2023)
Article
Multidisciplinary Sciences
Zahra Yekke-Ghasemi, Majid M. Heravi, Masoume Malmir, Masoud Mirzaei
Summary: In this study, a tri-component composite Zr/SiW12/GO was prepared using an ultrasonic-assisted method. This composite, acting as a remarkable heterogeneous catalyst, showed exceptional catalytic performance in the oxidation reaction of sulfides to sulfoxides. The composite also demonstrated exceptional stability and could be reused up to four times without significant loss in its catalytic activity.
SCIENTIFIC REPORTS
(2023)
Review
Chemistry, Multidisciplinary
Majid M. Heravi, Azadeh Nazari
Summary: Natural product synthesis is a constantly evolving field that evaluates new synthetic methods and reagents to address the complexities of structures and functions. SmI2, a widely-used reagent in chemical synthesis, has been highlighted in this review for its recent advances and strategies used in the total synthesis of natural products since 2004.
Review
Chemistry, Multidisciplinary
Majid M. Heravi, Vahideh Zadsirjan
Summary: The Hantzsch reaction is a well-known multi-component reaction for synthesizing 1,4-dihydropyridines, and microwave irradiation has been successfully utilized as a green energy source to promote this organic transformation. Literature survey shows that construction and aromatization of 1,4-DHPs can be effectively carried out under microwave irradiation in solution or dry media.
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.