scholarly journals Cellulose recycling as a source of raw chirality

2013 ◽  
Vol 85 (8) ◽  
pp. 1683-1692 ◽  
Author(s):  
Valeria Corne ◽  
María Celeste Botta ◽  
Enrique D. V. Giordano ◽  
Germán F. Giri ◽  
David F. Llompart ◽  
...  
Keyword(s):  
Organic Chemistry ◽  
Organic Carbon ◽  
Asymmetric Synthesis ◽  
Building Blocks ◽  
Biologically Active ◽  
Raw Material ◽  
Chiral Auxiliaries ◽  
High Chemical ◽  
Chiral Structure

Modern organic chemistry requires easily obtainable chiral building blocks that show high chemical versatility for their application in the synthesis of enantiopure compounds. Biomass has been demonstrated to be a widely available raw material that represents the only abundant source of renewable organic carbon. Through the pyrolitic conversion of cellulose or cellulose-containing materials it is possible to produce levoglucosenone, a highly functionalized chiral structure. This compound has been innovatively used as a template for the synthesis of key intermediates of biologically active products and for the preparation of chiral auxiliaries, catalysts, and organocatalysts for their application in asymmetric synthesis.

Remarkable Advances in the Asymmetric Synthesis of Biologically Active Natural Compounds from the Advent of Chiral Auxiliaries

2020 ◽  
pp. 1-51
Author(s):  
Gaspar Diaz-Muñoz ◽  
Izabel Luzia Miranda ◽  
Suélen Karine Sartori ◽  
Daniele Cristina de Rezende ◽  
Jefferson Viktor Barros de Paula Baeta ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Natural Compounds ◽  
Biologically Active ◽  
Chiral Auxiliaries ◽  
Active Natural

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.

Tandem allylboration-ring-closing metathesis reactions for the preparation of biologically active molecules

2003 ◽  
Vol 75 (9) ◽  
pp. 1263-1275 ◽  
Author(s):  
P. Veeraraghavan Ramachandran ◽  
M. Venkat Ram Reddy ◽  
Herbert C. Brown
Keyword(s):  
Organic Chemistry ◽  
Natural Products ◽  
Asymmetric Synthesis ◽  
Biologically Active ◽  
Cyclic Ethers ◽  
Ring Closing Metathesis ◽  
The Past ◽  
Metathesis Reactions

The development of asymmetric synthesis during the past two decades aided organic chemists considerably in the synthesis of complex natural products. Organoborane chemistry continues to play an important role in asymmetric synthesis. One of the important reactions that has become very common in the arsenal of synthetic chemists is allylboration and related reactions. Another important reaction that has recently attained enormous importance in organic chemistry is the ring-closing metathesis (RCM) reaction. Indeed, a combination of allylboration and RCM reactions provides an excellent route to cyclic ethers, lactones, lactams, etc. Herein, we describe a sequential asymmetric allylboration and RCM reaction protocol that has been utilized for the synthesis of several alpha-pyrone-containing natural products,particularly biologically active molecules.

Recent Applications in the Use of Sulfoxides as Chiral Auxiliaries for the Asymmetric Synthesis of Natural and Biologically Active Products

Synthesis ◽  
2020 ◽  
Vol 52 (07) ◽  
pp. 964-978 ◽  
Author(s):  
Xavier Salom-Roig ◽  
Claude Bauder
Keyword(s):  
Asymmetric Synthesis ◽  
Short Review ◽  
Diels Alder ◽  
Biologically Active ◽  
Aldol Reactions ◽  
Chiral Auxiliaries ◽  
Conjugate Additions ◽  
Chiral Sulfoxides ◽  
Diastereoselective Addition ◽  
Nazarov Cyclizations

The contribution of chiral sulfoxides as versatile auxiliaries in the field of organic chemistry has shown a prevalent interest in the asymmetric synthesis of natural products during the last 45 years. In this short review, we report the recent applications of these chiral auxiliaries to the synthesis of natural and biological active products highlighted from 2010 to 2019. We hope to allow the reader to have an overview of the potential of sulfoxide chemistry in the field of enantio­selective synthesis.1 Introduction2 Diastereoselective Additions to Ketones2.1 Reduction of β-Keto Sulfoxides2.2 Reduction of β-Keto Sulfoxides Followed by Bromohydrin Forma tion3 Synthesis of an α-Amino α′-Sulfinyl Ketone Followed by Diastere oselective Reduction of the β-Keto Sulfoxide4 Diastereoselective Addition of Carbanionic Chiral Sulfoxides4.1 Addition to an Aldehyde4.1.1 Aldol Reactions4.1.2 Reformatsky-Type Reactions4.2 Additions to Chiral Sulfinimines5 Diastereoselective Cyclization Reactions Directed by a Chiral Sulf oxide5.1 1,4-Radical Additions5.2 Intramolecular Conjugate Additions5.3 Nazarov Cyclizations5.4 Diels–Alder Reactions6 Atropodiastereoselective Synthesis7 Conclusion

Use of chiral auxiliaries in the asymmetric synthesis of biologically active compounds: A review

Chirality ◽  
2019 ◽  
Vol 31 (10) ◽  
pp. 776-812 ◽  
Author(s):  
Gaspar Diaz‐Muñoz ◽  
Izabel Luzia Miranda ◽  
Suélen Karine Sartori ◽  
Daniele Cristina Rezende ◽  
Marisa Alves Nogueira Diaz
Keyword(s):  
Asymmetric Synthesis ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Chiral Auxiliaries ◽  
Active Compounds

scholarly journals 1,3-Cyclohexadien-1-Als: Synthesis, Reactivity and Bioactivities

Molecules ◽  
2021 ◽  
Vol 26 (6) ◽  
pp. 1772
Author(s):  
Ignacio E. Tobal ◽  
Rocío Bautista ◽  
David Diez ◽  
Narciso M. Garrido ◽  
Pilar García-García
Keyword(s):  
Organic Chemistry ◽  
Building Block ◽  
Building Blocks ◽  
Natural Compounds ◽  
Diels Alder ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Complex Molecules ◽  
Active Compounds ◽  
Electron Withdrawing Group

In synthetic organic chemistry, there are very useful basic compounds known as building blocks. One of the main reactions wherein they are applied for the synthesis of complex molecules is the Diels–Alder cycloaddition. This reaction is between a diene and a dienophile. Among the most important dienes are the cyclic dienes, as they facilitate the reaction. This review considers the synthesis and reactivity of one of these dienes with special characteristics—it is cyclic and has an electron withdrawing group. This building block has been used for the synthesis of biologically active compounds and is present in natural compounds with interesting properties.

Technological aspects of alcohol distillates production from non-traditional sugar-raw materials

2021 ◽  
Vol 9 (16) ◽  
pp. 90-97
Author(s):  
Kateryna Danilova ◽  
◽  
Oksana Zavarzina ◽  
Keyword(s):  
Raw Materials ◽  
Biologically Active ◽  
Raw Material ◽  
Material Base ◽  
Growth Substances ◽  
Technological Properties ◽  
Actual Problem ◽  
Cane Molasses ◽  
Yeast Biomass ◽  
Nitrogen Phosphorus

An actual problem of the alcohol industry development is the expansion of the raw material base through the use of new, cheaper types of carbohydrate sources. Recently, glucose-fructose syrup has been of increasing interest to producers of ethanol. Among the producers of craft drinks, in particular rum-based drinks, cane molasses is in increasing demand. The article presents the technological aspects of the fermentation process of nonconventional sugar-containing raw materials on the example of glucose-fructose syrup and cane molasses in ethanol by different yeast strains. It is determined that glucose-fructose syrup and cane molasses are raw materials depleted of nitrogen, phosphorus and growth substances necessary for the yeast activity. To improve the technological properties of raw materials in the molasses, nitrogen, phosphorus nutrition and corn extract as a growth substance shall be added to a mash. Glucose-fructose syrup is of pH 3.68 and of acidity 0.12, which negatively affects the fermentation. It is established that in order to create optimal living conditions for yeast, it is necessary to add substances to the glucose-fructose syrup that will contribute to the safety of development and prevent the pH 3.5. It was determined that the alcohol yield from 1 ton of glucose-fructose syrup is 31.0 dal, from 1 ton of cane molasses is 24.0 dal on the yeast 46ED and 22 dal on the TegaYeast without the use of growth substances and vitamins necessary for the reproduction of yeast biomass. Under conditions of improving the technological properties of the mash from the glucose-fructose syrup and cane molasses by adding biologically active substances promoting the synthesis of yeast biomass, the ethanol content in the fermented mashes increases up to 11.9 12% vol.

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