Enantioselective syntheses of indanes: from organocatalysis to C–H functionalization

2016 ◽  
Vol 45 (5) ◽  
pp. 1368-1386 ◽  
Author(s):  
Cyril Borie ◽  
Lutz Ackermann ◽  
Malek Nechab
Keyword(s):  
Natural Products ◽  
Recent Progress ◽  
Enantioselective Catalysis ◽  
Enantioselective Syntheses ◽  
Major Progress

The indanyl core is ubiquitous in a large variety of drugs and natural products. Remarkable recent progress has been accomplished in the step-economical assembly of functionalization of chiral indanes by means of enantioselective catalysis, with major progress being achieved in organocatalysis and C–H activation chemistry.

Recent Progress Towards Synthesis of the Indolizidine Alkaloid 195B

2020 ◽  
Vol 17 (2) ◽  
pp. 82-90 ◽  
Author(s):  
Ghodsi Mohammadi Ziarani ◽  
Fatemeh Mohajer ◽  
Zohreh kheilkordi
Keyword(s):  
Natural Products ◽  
Natural Product ◽  
Recent Progress ◽  
Human Life ◽  
Natural Compounds ◽  
Biologically Active ◽  
Pharmaceutical Chemistry ◽  
Biological Perspective ◽  
Highly Active

Background: Natural products have been received attention due to their importance in human life as those are biologically active. In this review, there are some reports through different methods related to the synthesis of the indolizidine 195B which was extracted from poisonous frog; however, due to respect nature, the synthesis of natural compounds such as indolizidine has been attracted much attention among scientists and researchers. Objective: This review discloses the procedures and methods to provide indolizidine 195B from 1989 to 2018 due to their importance as a natural product. Conclusion: There are several methods to give rise to the indolizidine 195B as a natural product that is highly active from the biological perspective in pharmaceutical chemistry. In summary, many protocols for the preparations of indolizidine 195B from various substrates, several reagents, and conditions have been reported from different aromatic and aliphatic.

Enantioselective Syntheses of Flavonoid Diels-Alder Natural Products: A Review

2018 ◽  
Vol 15 (2) ◽  
pp. 221-229 ◽  
Author(s):  
Shah Bakhtiar Nasir ◽  
Noorsaadah Abd Rahman ◽  
Chin Fei Chee
Keyword(s):  
Natural Products ◽  
Organic Synthesis ◽  
Lewis Acid ◽  
Alder Reaction ◽  
Diels Alder ◽  
Enantioselective Synthesis ◽  
Chiral Ligand ◽  
Asymmetric Syntheses ◽  
Diels Alder Reaction ◽  
Enantioselective Syntheses

Background: The Diels-Alder reaction has been widely utilised in the syntheses of biologically important natural products over the years and continues to greatly impact modern synthetic methodology. Recent discovery of chiral organocatalysts, auxiliaries and ligands in organic synthesis has paved the way for their application in Diels-Alder chemistry with the goal to improve efficiency as well as stereochemistry. Objective: The review focuses on asymmetric syntheses of flavonoid Diels-Alder natural products that utilize chiral ligand-Lewis acid complexes through various illustrative examples. Conclusion: It is clear from the review that a significant amount of research has been done investigating various types of catalysts and chiral ligand-Lewis acid complexes for the enantioselective synthesis of flavonoid Diels-Alder natural products. The results have demonstrated improved yield and enantioselectivity. Much emphasis has been placed on the synthesis but important mechanistic work aimed at understanding the enantioselectivity has also been discussed.

scholarly journals Non-Enzymatic Desymmetrization Reactions in Aqueous Media

Symmetry ◽  
2021 ◽  
Vol 13 (4) ◽  
pp. 720
Author(s):  
Satomi Niwayama
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Functional Groups ◽  
Organic Compounds ◽  
Recent Progress ◽  
Aqueous Media ◽  
Building Blocks ◽  
Organic Reactions ◽  
Environmentally Benign ◽  
Enzymatic Desymmetrization

Symmetric organic compounds are generally obtained inexpensively, and therefore they can be attractive building blocks for the total synthesis of various pharmaceuticals and natural products. The drawback is that discriminating the identical functional groups in the symmetric compounds is difficult. Water is the most environmentally benign and inexpensive solvent. However, successful organic reactions in water are rather limited due to the hydrophobicity of organic compounds in general. Therefore, desymmetrization reactions in aqueous media are expected to offer versatile strategies for the synthesis of a variety of significant organic compounds. This review focuses on the recent progress of desymmetrization reactions of symmetric organic compounds in aqueous media without utilizing enzymes.

Recent progress in doxorubicin-induced cardiotoxicity and protective potential of natural products

Phytomedicine ◽  
2018 ◽  
Vol 40 ◽  
pp. 125-139 ◽  
Author(s):  
Jie Yu ◽  
Changxi Wang ◽  
Qi Kong ◽  
Xiaxia Wu ◽  
Jin-Jian Lu ◽  
...  
Keyword(s):  
Natural Products ◽  
Recent Progress ◽  
Protective Potential

scholarly journals Heterocycles as Moderators of Allyl Cation Cycloaddition Reactivity

Synlett ◽  
2017 ◽  
Vol 28 (18) ◽  
pp. 2345-2352 ◽  
Author(s):  
Johan Winne ◽  
Jan Hullaert ◽  
Bram Denoo ◽  
Mien Christiaens ◽  
Brenda Callebaut
Keyword(s):  
Natural Products ◽  
Recent Progress ◽  
Organic Transformations ◽  
Allyl Cation

For the rapid elaboration of polycarbocyclic scaffolds, prevalent in many important families of terpenoid natural products, allyl cations derived from simple heterocyclic alcohols can be used as versatile reaction partners in both (4+3) and (3+2) cycloaddition pathways. Our recent progress in this area is outlined, pointing towards the untapped potential of heterocycles to act as reagents in novel or known but challenging organic transformations.1 Heterocyclic Reagents2 Cycloadditions and Allyl Cations3 Furfuryl Cations in Cycloadditions4 Heterocycle-Substituted Cations in Cycloadditions5 Mechanistic Considerations6 Conclusions and Outlook

Recent progress of antibacterial natural products: Future antibiotics candidates

2020 ◽  
Vol 101 ◽  
pp. 103922 ◽  
Author(s):  
Jiangkun Dai ◽  
Rui Han ◽  
Yujie Xu ◽  
Na Li ◽  
Junru Wang ◽  
...  
Keyword(s):  
Natural Products ◽  
Recent Progress

scholarly journals N-(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds

2019 ◽  
Vol 15 ◽  
pp. 1722-1757
Author(s):  
Iwona E Głowacka ◽  
Aleksandra Trocha ◽  
Andrzej E Wróblewski ◽  
Dorota G Piotrowska
Keyword(s):  
Amino Acids ◽  
Natural Products ◽  
Natural Compounds ◽  
Review Article ◽  
Chiral Auxiliary ◽  
Biologically Relevant ◽  
Alternative Approaches ◽  
Approved Drugs ◽  
Enantioselective Syntheses ◽  
New Procedures

Since Garner’s aldehyde has several drawbacks, first of all is prone to racemization, alternative three-carbon chirons would be of great value in enantioselective syntheses of natural compounds and/or drugs. This review article summarizes applications of N-(1-phenylethyl)aziridine-2-carboxylates, -carbaldehydes and -methanols in syntheses of approved drugs and potential medications as well as of natural products mostly alkaloids but also sphingoids and ceramides and their 1- and 3-deoxy analogues and several hydroxy amino acids and their precursors. Designed strategies provided new procedures to several drugs and alternative approaches to natural products and proved efficiency of a 2-substituted N-(1-phenylethyl)aziridine framework as chiron bearing a chiral auxiliary.

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