Recent Advances in One-Pot Enyne Metathesis Processes for the Preparation of Biologically and Medicinally Relevant Compounds

Synthesis ◽  
2020 ◽  
Author(s):  
Massimo Serra ◽  
Eric Bernardi ◽  
Lino Colombo
Keyword(s):  
Environmental Sustainability ◽  
Scientific Literature ◽  
Diels Alder ◽  
Chemical Transformations ◽  
Enyne Metathesis ◽  
One Pot ◽  
Biologically Relevant ◽  
Bond Forming ◽  
Wide Range ◽  
Metal Catalyzed

AbstractEnyne metathesis reactions are powerful tools for the preparation of a wide range of synthetic and natural chemical substances with increasing efficiency and environmental sustainability. The driving force of the reaction is the formation of a stable conjugated system, i.e., a diene, which through further functionalization steps can be used for the construction of skeletally complex molecular architectures. These concepts are exploited to design cascade reaction sequences, where multiple rings can be formed in a one-pot fashion by combining metathetic protocols with various chemical transformations. The strong correlation between synthetic organic chemistry and medicinal chemistry prompted us to review the most notable approaches for the synthesis of biologically relevant compounds via enyne metathesis-based one-pot processes. With the aim to provide a modern and practical overview, by taking into consideration the scientific literature on this topic, we have focused the majority of our attention on the research performed in the last decade. This review covers the literature from 2003 to 2020.1 Introduction2 Ethylene-Mediated Processes3 RCEYM/CM and CEYM/RCM Processes4 Enyne Metathesis/Diels–Alder-Based Processes5 RCM of Dienynes6 RCM of Tethered Dienynes7 Relay Metathesis8 Ring-Rearrangement Metathesis9 RCEYM/Transition-Metal-Catalyzed C–C Bond-Forming Processes10 Conclusions11 List of Acronyms

Transition-Metal-Catalyzed Annulative Coupling Cascade for the Synthesis of 3-Methyleneisoindolin-1-ones

Synthesis ◽  
2020 ◽  
Vol 52 (06) ◽  
pp. 807-818 ◽  
Author(s):  
So Won Youn
Keyword(s):  
Transition Metal ◽  
Bond Formation ◽  
Short Review ◽  
Coupling Reactions ◽  
Cyclization Reactions ◽  
One Pot ◽  
Bond Forming ◽  
Wide Range ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

This short review describes the recent progress made on transition-metal-catalyzed annulative couplings for the synthesis of 3-methyleneisoindolin-1-ones, which are useful intermediates for the synthesis of numerous alkaloids and can be often found in a wide range of natural products and pharmaceuticals. In particular, new one-pot multiple C–C/C–N bond-forming processes for the construction of the 5-methylenepyrrol-2-one nucleus of such compounds are summarized.1 Introduction2 Intramolecular Cyclization Reactions: C3–N or C3–C3a and C–C Bond Formation3 Intermolecular Annulative Coupling Reactions3.1 C3–C3a and C3–N Bond Formation3.2 C1–C7a and C3–N Bond Formation3.3 C1–C7a and C1–N Bond Formation3.4 C1–C7a, C1–N and C3–N Bond Formation3.5 C3–C3a, C1–C7a, C1–N and C3–N Bond Formation: A Pd-Catalyzed One-Pot Sonogashira Coupling–Carbonylation–Amination–Cyclization Cascade4 Conclusion

scholarly journals Redox-Initiated Reversible Addition–Fragmentation Chain Transfer (RAFT) Polymerization

2019 ◽  
Vol 72 (7) ◽  
pp. 479 ◽  
Author(s):  
Amin Reyhani ◽  
Thomas G. McKenzie ◽  
Qiang Fu ◽  
Greg G. Qiao
Keyword(s):  
Redox Reactions ◽  
Chain Transfer ◽  
Raft Polymerization ◽  
Molecular Structures ◽  
Biologically Relevant ◽  
Molecular Weights ◽  
Polymeric Biomaterials ◽  
Reversible Addition ◽  
Wide Range ◽  
Metal Catalyzed

Reversible addition–fragmentation chain transfer (RAFT) polymerization initiated by a radical-forming redox reaction between a reducing and an oxidizing agent (i.e. ‘redox RAFT’) represents a simple, versatile, and highly useful platform for controlled polymer synthesis. Herein, the potency of a wide range of redox initiation systems including enzyme-mediated redox reactions, the Fenton reaction, peroxide-based reactions, and metal-catalyzed redox reactions, and their application in initiating RAFT polymerization, are reviewed. These redox-RAFT polymerization methods have been widely studied for synthesizing a broad range of homo- and co-polymers with tailored molecular weights, compositions, and (macro)molecular structures. It has been demonstrated that redox-RAFT polymerization holds particular promise due to its excellent performance under mild conditions, typically operating at room temperature. Redox-RAFT polymerization is therefore an important and core part of the RAFT methodology handbook and may be of particular importance going forward for the fabrication of polymeric biomaterials under biologically relevant conditions or in biological systems, in which naturally occurring redox reactions are prevalent.

Preparation of Tricyclic and Tetracyclic Benzoxepin Derivatives by One-Pot Enyne Metathesis/Diels-Alder Reaction

Synlett ◽  
2001 ◽  
Vol 2001 (11) ◽  
pp. 1784-1786 ◽  
Author(s):  
Marcial Moreno-Mañas ◽  
Roser Pleixats ◽  
Antoni Santamaria
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Enyne Metathesis ◽  
One Pot ◽  
Diels Alder Reaction

A Review on Synthetic Approaches of Phenanthridine

2021 ◽  
Vol 18 ◽  
Author(s):  
Nilesh Kshirsagar ◽  
Ratnamala Sonawane ◽  
Sultan Pathan ◽  
Ganesh Kamble ◽  
Girdhar Pal Singh
Keyword(s):  
Biological Activity ◽  
Transition Metal ◽  
Material Science ◽  
Anticancer Agent ◽  
Hypervalent Iodine ◽  
One Pot ◽  
Bond Forming ◽  
Microwave Assisted ◽  
Metal Catalyzed ◽  
Synthetic Approaches

Abstract: The phenanthridine family is widely found in medicinal chemistry and material science because of the biological activity and the presence in a variety of significant natural products and synthetic dye-stuffs. The phenanthridine has many clinical application like anticancer agent, antibacterial, antiprotozoal, pharmaceutically, and optoelectronic properties. Many methods have been reported for the synthesis of phenanthridine and phenanthridine alkaloids such as Pd catalyzed C-C bond forming. Reaction involving C-H activation , Radical, Microwave-assisted , transition metal catalyzed, one- pot cascade, benzyne mediated, photochemical, hypervalent iodine promoted ,etc. Here we summarized the literature data from 2014 to present concerning a novel or improved synthetic approaches.

Synthesis of New Polycyclic β-Lactams via One-Pot Enyne Metathesis and Diels-Alder Reactions

Synthesis ◽  
2004 ◽  
Vol 2004 (16) ◽  
pp. 2665-2672 ◽  
Author(s):  
Monique Savignac ◽  
Jean-Pierre Genêt ◽  
Nicolas Desroy ◽  
Fabien Robert-Peillard ◽  
Julie Toueg ◽  
...  
Keyword(s):  
Diels Alder ◽  
Enyne Metathesis ◽  
One Pot
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