Recent developments in the synthesis of azaindoles from pyridine and pyrrole building blocks

2021 ◽  
Author(s):  
Damoder Reddy Motati ◽  
Radhika Amaradhi ◽  
Thota Ganesh
Keyword(s):  
Natural Products ◽  
Building Blocks ◽  
Bioactive Natural Products ◽  
Biological Importance ◽  
Recent Developments ◽  
Synthetic Approaches

The azaindole framework is ubiquitous in bioactive natural products and pharmaceuticals. This review highlights the synthetic approaches to azaindoles with advantages and limitations, mechanistic pathways and biological importance.

Formation of Carbon-Oxygen Bond Mediated by Hypervalent Iodine Reagents Under Metal-free Conditions

2020 ◽  
Vol 17 ◽  
Author(s):  
Ayesha Jalil ◽  
Yaxin O Yang ◽  
Zhendong Chen ◽  
Rongxuan Jia ◽  
Tianhao Bi ◽  
...  
Keyword(s):  
Natural Products ◽  
Bond Formation ◽  
Building Blocks ◽  
Review Article ◽  
Hypervalent Iodine ◽  
Metal Free ◽  
Bioactive Natural Products ◽  
The Past ◽  
Oxygen Bond ◽  
Privileged Scaffolds

: Hypervalent iodine reagents are a class of non-metallic oxidants have been widely used in the construction of several sorts of bond formations. This surging interest in hypervalent iodine reagents is essentially due to their very useful oxidizing properties, combined with their benign environmental character and commercial availability from the past few decades ago. Furthermore, these hypervalent iodine reagents have been used in the construction of many significant building blocks and privileged scaffolds of bioactive natural products. The purpose of writing this review article is to explore all the transformations in which carbon-oxygen bond formation occurred by using hypervalent iodine reagents under metal-free conditions

Electrocatalytic Difunctionalization of Olefins as a General Approach to the Synthesis of Vicinal Diamines

Synlett ◽  
2018 ◽  
Vol 29 (03) ◽  
pp. 257-265 ◽  
Author(s):  
Song Lin ◽  
Joseph Parry ◽  
Niankai Fu
Keyword(s):  
Natural Products ◽  
Building Blocks ◽  
Therapeutic Agents ◽  
Recent Contribution ◽  
Structural Motifs ◽  
Bioactive Natural Products ◽  
Methodological Approaches ◽  
Molecular Catalysts ◽  
Vicinal Diamines

Vicinal diamines are highly prevalent structural motifs in therapeutic agents, bioactive natural products, and molecular catalysts. However, there are currently few unified methodological approaches for making these pertinent synthetic building blocks. This Synpacts article provides an overview of selected landmark developments in the area of olefin diamination. In particular, we highlight our recent contribution on the electrocatalytic diazidation of olefins as a general, selective, and sustainable method for the synthesis of vicinal diamines.1 Introduction2 Background: Intermolecular Diamination of Olefins3 Background: Intermolecular Diazidation of Olefins4 Electrocatalytic Diazidation of Olefins

scholarly journals Borylation and rearrangement of alkynyloxiranes: a stereospecific route to substituted α-enynes

2019 ◽  
Vol 15 ◽  
pp. 1416-1424
Author(s):  
Ruben Pomar Fuentespina ◽  
José Angel Garcia de la Cruz ◽  
Gabriel Durin ◽  
Victor Mamane ◽  
Jean-Marc Weibel ◽  
...  
Keyword(s):  
Organic Synthesis ◽  
Cross Coupling ◽  
Functional Materials ◽  
Building Blocks ◽  
Cascade Process ◽  
Coupling Reactions ◽  
One Pot ◽  
Bioactive Natural Products ◽  
Cross Coupling Reactions ◽  
Synthetic Approaches

1,3-Enynes are important building blocks in organic synthesis and also constitute the key motif in various bioactive natural products and functional materials. However, synthetic approaches to stereodefined substituted 1,3-enynes remain a challenge, as they are limited to Wittig and cross-coupling reactions. Herein, stereodefined 1,3-enynes, including tetrasubstituted ones, were straightforwardly synthesized from cis or trans-alkynylated oxiranes in good to excellent yields by a one-pot cascade process. The procedure relies on oxirane deprotonation, borylation and a stereospecific rearrangement of the so-formed alkynyloxiranyl borates. This stereospecific process overall transfers the cis or trans-stereochemistry of the starting alkynyloxiranes to the resulting 1,3-enynes.

Sharpless Asymmetric Epoxidation: Applications in the Synthesis of Bioactive Natural Products

2020 ◽  
Vol 17 ◽  
Author(s):  
Suélen Karine Sartori ◽  
Izabel Luzia Miranda ◽  
Marisa Alves Nogueira Diaz ◽  
Gaspar Diaz-Muñoz
Keyword(s):  
Natural Products ◽  
Building Blocks ◽  
Heterocyclic Ring ◽  
Biologically Active ◽  
Asymmetric Epoxidation ◽  
Allylic Alcohols ◽  
Titanium Tetraisopropoxide ◽  
Bioactive Natural Products ◽  
Tert Butyl Hydroperoxide ◽  
Sharpless Asymmetric Epoxidation

: This review discusses an important synthetic tool proposed by K. B. Sharpless in 1980, known as the Sharpless asymmetric epoxidation of allylic alcohols, and examines its use in the total synthesis of representative exponents of biologically active natural products. Focus is given to the synthesis of simple to highly complex secondary metabolites, including lactones, amino acids, diterpenes, and macrolides. The Sharpless approach involves the use of a catalyst, titanium tetraisopropoxide [Ti(OiPr)4], dialkyl tartrate as chiral ligand, and tert-butyl hydroperoxide (TBHP) as oxidizing agent. The method allows converting allylic alcohols to epoxides, which are chiral building blocks and versatile intermediates in the synthesis of natural products. The biological and synthetic importance of epoxides lies in the susceptibility of the threemembered heterocyclic ring to stereo- and regioselective opening by nucleophilic or acidic reagents, providing oxygen adducts.

Recent achievements in the synthesis of oxazoles

2021 ◽  
Vol 25 ◽  
Author(s):  
Dau Xuan Duc ◽  
Nguyen Thi Chung
Keyword(s):  
Natural Products ◽  
Biological Activities ◽  
Agricultural Fields ◽  
Disease Treatment ◽  
Bioactive Natural Products ◽  
Antiviral Activities ◽  
Novel Methods ◽  
Anti Inflammatory ◽  
Synthetic Approaches ◽  
Synthetic Transformations

: Oxazole-containing compounds have diverse biological activities, such as antimicrobial, anticancer, antitubercular, anti-inflammatory, antidiabetic, antiobesity, antimalarial, and antiviral activities, and some of them have been used as drugs for disease treatment. They also play important roles in the synthesis of bioactive natural products, pharmaceuticals, and synthetic transformations, as well as in materials, catalysts, and agricultural fields. Thus, the development of more efficient and facile synthetic approaches to access oxazole compounds has attracted the intensive interest of chemists, and diverse methods for their synthesis have been investigated. Various established methods have been improved and modified, while numerous novel methods have been discovered. This article summarizes considerable studies on the construction of the oxazole skeleton, which date back to 2014.

Combining biocatalysis and organocatalysis for the synthesis of piperidine alkaloids.

2022 ◽  
Author(s):  
Freya Taday ◽  
Ryan Cairns ◽  
Adam O'Connell ◽  
Elaine O'Reilly
Keyword(s):  
Natural Products ◽  
Building Blocks ◽  
Piperidine Alkaloids ◽  
Bioactive Natural Products ◽  
Cascade Processes

There is continued interest in developing cascade processes for the synthesis of key chiral building blocks and bioactive natural products (or analogues). Here, we report a hybrid bio-organocatalytic cascade for...

scholarly journals Recent Advances in the Synthesis of β-Carboline Alkaloids

Molecules ◽  
2021 ◽  
Vol 26 (3) ◽  
pp. 663
Author(s):  
Tímea Szabó ◽  
Balázs Volk ◽  
Mátyás Milen
Keyword(s):  
Natural Products ◽  
Pharmacological Activity ◽  
Heterocyclic Compounds ◽  
Biological Activities ◽  
Antimicrobial Drug ◽  
Drug Candidates ◽  
Recent Developments ◽  
Pharmacological Potential ◽  
Key Steps ◽  
Synthetic Approaches

β-Carboline alkaloids are a remarkable family of natural and synthetic indole-containing heterocyclic compounds and they are widely distributed in nature. Recently, these alkaloids have been in the focus of interest, thanks to their diverse biological activities. Their pharmacological activity makes them desirable as sedative, anxiolytic, hypnotic, anticonvulsant, antitumor, antiviral, antiparasitic or antimicrobial drug candidates. The growing potential inherent in them encourages many researchers to address the challenges of the synthesis of natural products containing complex β-carboline frameworks. In this review, we describe the recent developments in the synthesis of β-carboline alkaloids and closely related derivatives through selected examples from the last 5 years. The focus is on the key steps with improved procedures and synthetic approaches. Furthermore the pharmacological potential of the alkaloids is also highlighted.

scholarly journals Engineering the acyltransferase substrate specificity of assembly line polyketide synthases

2013 ◽  
Vol 10 (85) ◽  
pp. 20130297 ◽  
Author(s):  
Briana J. Dunn ◽  
Chaitan Khosla
Keyword(s):  
Natural Products ◽  
Substrate Specificity ◽  
Assembly Line ◽  
Current Knowledge ◽  
Structural Diversity ◽  
Structural Data ◽  
Building Blocks ◽  
Polyketide Synthases ◽  
Biologically Active ◽  
Recent Developments

Polyketide natural products act as a broad range of therapeutics, including antibiotics, immunosuppressants and anti-cancer agents. This therapeutic diversity stems from the structural diversity of these small molecules, many of which are produced in an assembly line manner by modular polyketide synthases. The acyltransferase (AT) domains of these megasynthases are responsible for selection and incorporation of simple monomeric building blocks, and are thus responsible for a large amount of the resulting polyketide structural diversity. The substrate specificity of these domains is often targeted for engineering in the generation of novel, therapeutically active natural products. This review outlines recent developments that can be used in the successful engineering of these domains, including AT sequence and structural data, mechanistic insights and the production of a diverse pool of extender units. It also provides an overview of previous AT domain engineering attempts, and concludes with proposed engineering approaches that take advantage of current knowledge. These approaches may lead to successful production of biologically active ‘unnatural’ natural products.

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