scholarly journals Biochemical Asymmetric Synthesis and Its Application to Chemical Synthesis of Bioactive Compounds.

1995 ◽  
Vol 69 (1) ◽  
pp. 9-16
Author(s):  
Takeshi Sugai
2020 ◽  
Vol 20 (28) ◽  
pp. 2520-2534
Author(s):  
He Huang ◽  
Chuanjun Song ◽  
Junbiao Chang

: Tanshinones are a class of bioactive compounds present in the Chinese herbal medicine Danshen (Salvia miltiorrhiza Bunge), containing among others, abietane diterpene quinone scaffolds. Chemical synthesis and biological activity studies of natural and unnatural tanshinone derivatives have been reviewed in this article.


2019 ◽  
Vol 800 ◽  
pp. 36-41
Author(s):  
Evija Rolava ◽  
Jevgeņija Lugiņina ◽  
Māris Turks

Oxazolidinones are an important class of heterocyclic compounds that are used as chiral auxiliaries in asymmetric synthesis and as biologically active pharmaceutical agents. Moreover, carbohydrates are ideal scaffolds to generate libraries of bioactive compounds due the presence of defined configuration. We report here asymmetric alkylation studies on N-derivatized glucose-and allose-based spirooxazolidinones which do act as chiral auxiliaries.


Synthesis ◽  
2020 ◽  
Vol 53 (01) ◽  
pp. 107-122
Author(s):  
Jean-François Brière ◽  
Mario Waser ◽  
Antonio Massa ◽  
Antonio Macchia ◽  
Andreas Eitzinger

AbstractIsoxazol-5-ones and isoxazolidin-5-ones represent two important classes of heterocycles, with several applications as bioactive compounds and as versatile building blocks for further transformations. Unlike the parent aromatic isoxazoles, the presence of one or two stereocenters in the ring renders their asymmetric construction particularly important. In this review, starting from the description of general features and differences between these two related compound families, we present an overview on the most important enantioselective synthesis strategies to access these heterocycles. Both chiral metal catalysts and organocatalysts have recently been successfully employed for this task and some of the most promising approaches will be discussed.1 Introduction2 Isoxazol-5-ones as Nucleophiles2.1 Isoxazol-5-ones as C-Nucleophiles2.2 Isoxazol-5-ones as N-Nucleophiles2.3 Isoxazol-5-ones as C-Nucleophiles in Cyclization Processes3 Asymmetric Construction of Isoxazolidin-5-ones3.1 Enantioselective α-Functionalizations of Isoxazolidin-5-ones4 Arylideneisoxazol-5-ones in Conjugated Addition5 Conclusions


Nanoscale ◽  
2021 ◽  
Author(s):  
Mariya A. Zvaigzne ◽  
Pavel Samokhvalov ◽  
Yurii Gun'ko ◽  
Igor Nabiev

The production of enantiopure chemicals is an essential part of modern chemical industry. Hence, the emergence of asymmetric catalysis led to dramatic changes in the procedures of chemical synthesis, and...


2021 ◽  
Vol 18 ◽  
Author(s):  
Estibaliz Sansinenea ◽  
Aurelio Ortiz

Background: The total syntheses of complex natural products have evolved to include new methodologies to save time, simplifying the form to achieve these natural compounds. Objective: In this review, we have described the asymmetric synthesis of different natural products and biologically active compounds of the last ten years until the current day. Results: An asymmetric organocatalytic reaction is the key to generate stereoselectively the main structure with the required stereochemistry. Conclusion: Even more remarkable, the organocatalytic cascade reactions, which are carried out with high stereoselectivity, as well as a possible approximation of the organocatalysts activation with substrates are also described.


Author(s):  
Kai Zhang ◽  
Yuanzhi He ◽  
Jiawei Zhu ◽  
Qi Zhang ◽  
Luyao Tang ◽  
...  

Reductive aminases (RedAms) for the stereoselective amination of ketones represent an environmentally benign and economically viable alternative to transition metal–catalyzed asymmetric chemical synthesis. Here, we report two RedAms from Aspergillus calidoustus (AcRedAm) and bacteria (BaRedAm) with NADPH-dependent features. The enzymes can synthesize a set of secondary amines using a broad range of ketone and amine substrates with up to 97% conversion. To synthesize the pharmaceutical ingredient (R)-rasagiline, we engineered AcRedAm through rational design to obtain highly stereoselective mutants. The best mutant Q237A from AcRedAm could synthesize (R)-rasagiline with >99% enantiomeric excess with moderate conversion. The features of AcRedAm and BaRedAm highlight their potential for further study and expand the biocatalytic toolbox for industrial applications.


2021 ◽  
Vol 25 ◽  
Author(s):  
Martina Bortolami ◽  
Francesca Leonelli ◽  
Marta Feroci ◽  
Fabrizio Vetica

: Oxindoles are an important class of heterocyclic scaffolds widely present in natural products and bioactive compounds. For this reason, a plethora of methodologies for the stereoselective synthesis of enantioenriched oxindoles has been studied over the years. Among all the reported synthetic strategies, organocatalysis has proven to be a powerful tool for the asymmetric synthesis of this class of compounds being a step- and atom-economical, environmentally friendly, and non-toxic approach. This review will outline the application of asymmetric organocatalysis in the synthesis of chiral oxindole-based structures, relying on domino/one-pot reaction sequences in a step-economical fashion.


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