Recent advances in the asymmetric synthesis of pharmacology-relevant nitrogen heterocycles via stereoselective aza-Michael reactions

2019 ◽  
Vol 17 (15) ◽  
pp. 3670-3708 ◽  
Author(s):  
Maxim G. Vinogradov ◽  
Olga V. Turova ◽  
Sergei G. Zlotin
Keyword(s):  
Asymmetric Synthesis ◽  
Michael Reaction ◽  
Nitrogen Heterocycles ◽  
Michael Reactions ◽  
Naturally Occurring ◽  
Recent Advances

In this review, recent applications of a stereoselective aza-Michael reaction for asymmetric synthesis of naturally occurring N-containing heterocyclic scaffolds and their usefulness to pharmacology are summarized.

scholarly journals Recent Advance of Domino Michael Reaction in Natural Product Synthesis

2021 ◽  
Vol 16 (10) ◽  
pp. 1934578X2110498
Author(s):  
Hisahiro Hagiwara
Keyword(s):  
Natural Products ◽  
Natural Product ◽  
Michael Reaction ◽  
Natural Product Synthesis ◽  
Total Syntheses ◽  
Michael Reactions ◽  
Recent Advances ◽  
Key Steps ◽  
Related Compounds

Recent advances in the total syntheses of cyclic natural products and related compounds from 2005 to 2021, which employ domino Michael reactions as key steps, have been reviewed, focusing mainly on the domino Michael reactions catalyzed by organocatalysts.

Recent Advances in Catalytic Enantioselective Synthesis of Pyrazolones with a Tetrasubstituted Stereogenic Center at the 4-Position

Synthesis ◽  
2020 ◽  
Vol 53 (02) ◽  
pp. 215-237
Author(s):  
José R. Pedro ◽  
Carlos Vila ◽  
Laura Carceller-Ferrer ◽  
Gonzalo Blay
Keyword(s):  
Biological Activity ◽  
Asymmetric Synthesis ◽  
Nitrogen Heterocycles ◽  
Enantioselective Synthesis ◽  
Great Success ◽  
Pharmaceutical Drugs ◽  
Quaternary Carbon ◽  
Recent Advances ◽  
Excellent Research ◽  
Stereogenic Center

AbstractPyrazolone [2,4-dihydro-3H-pyrazol-4-one] represents one of the most important five-membered nitrogen heterocycles which is present in numerous pharmaceutical drugs and molecules with biological activity. Recently, many catalytic methodologies for the asymmetric synthesis of chiral pyrazolones have been established with great success, specially, for the synthesis of pyrazolones bearing a tetrasubstituted stereocenter at C-4. This review summarizes these excellent research studies since 2018, including representative examples and some mechanistic pathways explaining the observed stereochemistry.1 Introduction2 Catalytic Enantioselective Synthesis of Chiral Pyrazolones with a Full Carbon Tetrasubstituted Stereocenter at C-43 Catalytic Enantioselective Synthesis of Chiral Pyrazolones with a Quaternary Carbon Stereocenter at C-4 bearing a Heteroatom4 Catalytic Enantioselective Synthesis of Chiral Spiropyrazolones5 Conclusion

Asymmetric synthesis of highly functionalized furanones via direct Michael reactions mediated by a bulky primary amine

2019 ◽  
Vol 6 (8) ◽  
pp. 1080-1083 ◽  
Author(s):  
Huicai Huang ◽  
Xue Lu ◽  
Yukang Mao ◽  
Jinxing Ye
Keyword(s):  
Asymmetric Synthesis ◽  
Primary Amine ◽  
Michael Reaction ◽  
Michael Reactions

A bulky chiral primary amine catalyzed Michael reaction of 3(2H)-furanones has been realized, leading to the construction of substituted furanone derivatives.

A REVIEW ON RECENT ADVANCES IN CHEMISTRY, SYNTHESIS AND BIOLOGICAL APPLICATIONS OF ISATIN DERIVATIVES

2018 ◽  
pp. 16-22
Author(s):  
Shukla PK ◽  
Singh MP ◽  
Patel R
Keyword(s):  
Heterocyclic Compounds ◽  
Biologically Active ◽  
Biological Applications ◽  
Plant Origin ◽  
Recent Past ◽  
Pharmacological Activities ◽  
Naturally Occurring ◽  
Recent Advances ◽  
Biological Aspects ◽  
Isatin Derivatives

Indole and its derivatives have engaged a unique place in the chemistry of nitrogen heterocyclic compounds. The recognition of the plant growthhormone, heteroauxin, the significant amino acids, tryptamine & tryptophan and anti-inflammatory drug, indomethacine are the imperativederivatives of indole which have added stimulus to this review work. Isatin (1H-indole-2,3-dione), an indole derivative of plant origin. Althoughit is a naturally occurring compound, but was synthesized by Erdmann and Laurent in 1840 before it was found in nature. Isatin is a versatileprecursor for many biologically active molecules and its diversified nature makes it a versatile substrate for further modifications. It is concernedin many pharmacological activities like anti-malarial, antiviral, anti-allergic, antimicrobial etc; isatin and its derivatives have been also found todemonstrate promising outcomes against various cancer cell lines. This review provides a brief overview on the recent advances and futureperspectives on chemistry and biological aspects of isatin and its derivatives reported in the recent past.

Enantioselective Functionalization of Prochiral Cyclobutanones and Cyclobutenones

Synlett ◽  
2021 ◽  
Author(s):  
Memg Wang ◽  
Changxu Zhong ◽  
Ping Lu
Keyword(s):  
Asymmetric Synthesis ◽  
Membered Ring ◽  
Enantioselective Synthesis ◽  
Ring Compounds ◽  
Recent Advances ◽  
Cyclobutane Derivatives

Enantioselective synthesis of cyclobutane derivatives is still a challenging topic in asymmetric synthesis. [2+2]-Cycloaddition and skeleton rearrangement are two primary strategies to this end. Recently, functionalization of cyclobutanones and cyclobutenones, which are readily available via [2+2]-cycloadditions as prochiral substrates, has emerged as a powerful tool to access versatile four-membered ring compounds. Herein, we summarize some recent advances in these areas from our and other groups.

ChemInform Abstract: Base-Dependent Stereodivergent Intramolecular Aza-Michael Reaction: Asymmetric Synthesis of 1,3-Disubstituted Isoindolines.

ChemInform ◽  
2014 ◽  
Vol 45 (3) ◽  
pp. no-no
Author(s):  
Santos Fustero ◽  
Lidia Herrera ◽  
Ruben Lazaro ◽  
Elsa Rodriguez ◽  
Miguel A. Maestro ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Michael Reaction

scholarly journals Epsilon-poly-L-lysine: Recent Advances in Biomanufacturing and Applications

2021 ◽  
Vol 9 ◽  
Author(s):  
Liang Wang ◽  
Chongyang Zhang ◽  
Jianhua Zhang ◽  
Zhiming Rao ◽  
Xueming Xu ◽  
...  
Keyword(s):  
Industrial Waste ◽  
Genome Mining ◽  
Process Engineering ◽  
Polymerization Degree ◽  
Future Perspectives ◽  
Naturally Occurring ◽  
Recent Advances ◽  
Wild Strains ◽  
Purification Methods ◽  
Pharmaceutical Industries

ε-poly-L-lysine (ε-PL) is a naturally occurring poly(amino acid) of varying polymerization degree, which possesses excellent antimicrobial activity and has been widely used in food and pharmaceutical industries. To provide new perspectives from recent advances, this review compares several conventional and advanced strategies for the discovery of wild strains and development of high-producing strains, including isolation and culture-based traditional methods as well as genome mining and directed evolution. We also summarize process engineering approaches for improving production, including optimization of environmental conditions and utilization of industrial waste. Then, efficient downstream purification methods are described, including their drawbacks, followed by the brief introductions of proposed antimicrobial mechanisms of ε-PL and its recent applications. Finally, we discuss persistent challenges and future perspectives for the commercialization of ε-PL.

Asymmetric Synthesis of Unsaturated Monocyclic and Bicyclic Nitrogen Heterocycles

2009 ◽  
Vol 11 (13) ◽  
pp. 2892-2895 ◽  
Author(s):  
Hiroshi Nomura ◽  
Christopher J. Richards
Keyword(s):  
Asymmetric Synthesis ◽  
Nitrogen Heterocycles
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