Asymmetric Organocatalytic Syntheses of Bioactive Compounds

2021 ◽  
Vol 18 ◽  
Author(s):  
Estibaliz Sansinenea ◽  
Aurelio Ortiz
Keyword(s):  
Natural Products ◽  
Asymmetric Synthesis ◽  
Bioactive Compounds ◽  
Cascade Reactions ◽  
Biologically Active ◽  
Active Compounds ◽  
Total Syntheses ◽  
Main Structure ◽  
New Methodologies ◽  
High Stereoselectivity

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.

Glucose - and Allose-Derived Chiral Auxiliaries

2019 ◽  
Vol 800 ◽  
pp. 36-41
Author(s):  
Evija Rolava ◽  
Jevgeņija Lugiņina ◽  
Māris Turks
Keyword(s):  
Asymmetric Synthesis ◽  
Bioactive Compounds ◽  
Heterocyclic Compounds ◽  
Biologically Active ◽  
Important Class ◽  
Chiral Auxiliaries ◽  
Asymmetric Alkylation ◽  
Pharmaceutical Agents

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.

The Potential of Biologically Active Brazilian Plant Species as a Strategy to Search for Molecular Models for Mosquito Control

Planta Medica ◽  
2020 ◽  
Author(s):  
Marilia Valli ◽  
Letícia Cristina Vieira Atanázio ◽  
Gustavo Claro Monteiro ◽  
Roberta Ramos Coelho ◽  
Daniel Pecoraro Demarque ◽  
...  
Keyword(s):  
Natural Products ◽  
Drug Discovery ◽  
Vector Control ◽  
Plant Species ◽  
Mosquito Control ◽  
Biologically Active ◽  
Molecular Models ◽  
Public Health Importance ◽  
Active Compounds ◽  
Brazilian Biodiversity

AbstractNatural products are a valuable source of biologically active compounds and continue to play an important role in modern drug discovery due to their great structural diversity and unique biological properties. Brazilian biodiversity is one of the most extensive in the world and could be an effective source of new chemical entities for drug discovery. Mosquitoes are vectors for the transmission of dengue, Zika, chikungunya, yellow fever, and many other diseases of public health importance. These diseases have a major impact on tropical and subtropical countries, and their incidence has increased dramatically in recent decades, reaching billions of people at risk worldwide. The prevention of these diseases is mainly through vector control, which is becoming more difficult because of the emergence of resistant mosquito populations to the chemical insecticides. Strategies to provide efficient and safe vector control are needed, and secondary metabolites from plant species from the Brazilian biodiversity, especially Cerrado, that are biologically active for mosquito control are herein highlighted. Also, this is a literature revision of targets as insights to promote advances in the task of developing active compounds for vector control. In view of the expansion and occurrence of arboviruses diseases worldwide, scientific reviews on bioactive natural products are important to provide molecular models for vector control and contribute with effective measures to reduce their incidence.

scholarly journals Recent applications of imines as key intermediates in the synthesis of alkaloids and novel nitrogen heterocycles

2009 ◽  
Vol 81 (2) ◽  
pp. 195-204 ◽  
Author(s):  
Stephen F. Martin
Keyword(s):  
Organic Chemistry ◽  
Natural Products ◽  
Multicomponent Reactions ◽  
Nitrogen Heterocycles ◽  
Biologically Active ◽  
Total Syntheses ◽  
Biological Interest ◽  
Cascade Processes ◽  
Novel Applications ◽  
Active Natural

One of the major challenges in contemporary synthetic organic chemistry is the design and development of new tactics and strategies and their application to concise and efficient syntheses of biologically active natural products. Strategies that utilize reactions that enable the rapid assembly of the skeletal framework of such targets are thus especially attractive. In this context, we have developed novel applications of imine chemistry in Mannich and related reactions, cascade processes, and multicomponent reactions (MCRs) to rapidly assemble structural subunits common to diverse families of alkaloids. The practical utility of these chemistries is evidenced by their use in the execution of facile total syntheses of (±)-epilupinine (1), (±)-tashiromine (2), (-)-epimyrtine (3), and (±)-roelactamine (4) as well as other nitrogen heterocycles of potential biological interest.

Diversity-Oriented Synthesis of Natural Products via Gold-Catalyzed Cascade Reactions

Synlett ◽  
2018 ◽  
Vol 29 (12) ◽  
pp. 1552-1571 ◽  
Author(s):  
Jianxian Gong ◽  
Zhen Yang ◽  
Yueqing Gu ◽  
Ceheng Tan
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Cascade Reactions ◽  
Cascade Reaction ◽  
Biologically Active ◽  
Synthetic Methods ◽  
Left Wing ◽  
Asymmetric Total Synthesis ◽  
Diversity Oriented Synthesis ◽  
Active Natural

This account describes our group’s latest research in the field of diversity-oriented synthesis of natural products via gold-catalyzed cascade reactions. We present two general strategies based on gold-catalyzed cycloisomerization: a gold-catalyzed cascade reaction of 1,7-diynes and a pinacol-terminated gold-catalyzed cascade reaction. We highlight our development of synthetic methods for the construction of biologically active natural products by using these two strategies.1 Introduction2 Gold-Catalyzed Cascade Reactions of 1,7-Diynes2.1 Collective Synthesis of C15 Oxygenated Drimane-Type Sesquiterpenoids2.2 Synthesis of Left-Wing Fragment of Azadirachtin I2.3 Collective Synthesis of Cladiellins3 Pinacol-Terminated Gold-Catalyzed Cascade Reaction3.1 Asymmetric Formal Total Synthesis of (+)-Cortistatins3.2 Total Synthesis of Orientalol F3.3 Asymmetric Total Synthesis of (–)-Farnesiferol C4 Summary and Outlook

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