General, Highly Selective Synthesis of 1,3- and 1,4-Difunctionalized Building Blocks by Regiodivergent Epoxide Opening

2016 ◽  
Vol 55 (39) ◽  
pp. 12030-12034 ◽  
Author(s):  
Nico Funken ◽  
Felix Mühlhaus ◽  
Andreas Gansäuer
Keyword(s):  
Building Blocks ◽  
Selective Synthesis ◽  
Epoxide Opening

General, Highly Selective Synthesis of 1,3- and 1,4-Difunctionalized Building Blocks by Regiodivergent Epoxide Opening

2016 ◽  
Vol 128 (39) ◽  
pp. 12209-12213 ◽  
Author(s):  
Nico Funken ◽  
Felix Mühlhaus ◽  
Andreas Gansäuer
Keyword(s):  
Building Blocks ◽  
Selective Synthesis ◽  
Epoxide Opening

scholarly journals Polyhalonitrobutadienes as Versatile Building Blocks for the Biotargeted Synthesis of Substituted N-Heterocyclic Compounds

Molecules ◽  
2020 ◽  
Vol 25 (12) ◽  
pp. 2863 ◽  
Author(s):  
Viktor A. Zapol’skii ◽  
Ursula Bilitewski ◽  
Sören R. Kupiec ◽  
Isabell Ramming ◽  
Dieter E. Kaufmann
Keyword(s):  
Staphylococcus Aureus ◽  
Antibacterial Activity ◽  
Heterocyclic Compounds ◽  
Nitrogen Heterocycles ◽  
Building Blocks ◽  
Antibacterial Activities ◽  
Synthetic Approach ◽  
Selective Synthesis ◽  
Ic50 Values ◽  
Thiophene Derivatives

Substituted nitrogen heterocycles are structural key units in many important pharmaceuticals. A new synthetic approach towards heterocyclic compounds displaying antibacterial activity against Staphylococcus aureus or cytotoxic activity has been developed. The selective synthesis of a series of 64 new N-heterocycles from the three nitrobutadienes 2-nitroperchloro-1,3-butadiene, 4-bromotetrachloro-2-nitro-1,3-butadiene and (Z)-1,1,4-trichloro-2,4-dinitrobuta-1,3-diene proved feasible. Their reactions with N-, O- and S-nucleophiles provide rapid access to push-pull substituted benzoxazolines, benzimidazolines, imidazolidines, thiazolidinones, pyrazoles, pyrimidines, pyridopyrimidines, benzoquinolines, isothiazoles, dihydroisoxazoles, and thiophenes with unique substitution patterns. Antibacterial activities of 64 synthesized compounds were examined. Additionally, seven compounds (thiazolidinone, nitropyrimidine, indole, pyridopyrimidine, and thiophene derivatives) exhibited a significant cytotoxicity with IC50-values from 1.05 to 20.1 µM. In conclusion, it was demonstrated that polyhalonitrobutadienes have an interesting potential as structural backbones for a variety of highly functionalized, pharmaceutically active heterocycles.

Cu ion-exchanged and Cu nanoparticles decorated mesoporous ZSM-5 catalysts for the activation and utilization of phenylacetylene in a sustainable chemical synthesis

RSC Advances ◽  
2016 ◽  
Vol 6 (90) ◽  
pp. 87066-87081 ◽  
Author(s):  
Bhaskar Sarmah ◽  
Biswarup Satpati ◽  
Rajendra Srivastava
Keyword(s):  
Chemical Synthesis ◽  
External Surface ◽  
Building Blocks ◽  
Selective Synthesis ◽  
Cu Nanoparticles ◽  
Excellent Activity ◽  
Highly Dispersed

Highly dispersed Cu nanoparticles supported on the large external surface of Meso-ZSM-5 exhibited excellent activity in the selective synthesis of indolizines, chalcones, and triazoles using phenylacetylene as one of the building blocks.

scholarly journals Diaryltin Dihydrides and Aryltin Trihydrides with Intriguing Stability

Molecules ◽  
2020 ◽  
Vol 25 (5) ◽  
pp. 1076
Author(s):  
Beate G. Steller ◽  
Berenike Doler ◽  
Roland C. Fischer
Keyword(s):  
Thermal Stability ◽  
Special Interest ◽  
Organometallic Compounds ◽  
Building Blocks ◽  
High Thermal Stability ◽  
Selective Synthesis ◽  
Oxygen Tolerance

In the last few decades, organotin hydrides have proven their potential as building blocks for a great variety of organometallic compounds. In this context, organotin hydrides with sterically shielding aryl substituents have attracted special interest, as these ligands can kinetically stabilize metastable products. The selective synthesis of aryltin halide compounds Ar*2SnCl2 and Ar*SnI3 featuring the highly sterically encumbered aryl ligand Ar* (iPrAr* = 2,6-(Ph2CH)2-4-iPrC6H2; MeAr* = 2,6-(Ph2CH)2-4-MeC6H2) is presented. These aryltin halides were converted into corresponding aryltin hydrides Ar*2SnH2 and Ar*SnH3, which exhibit a surprisingly high thermal stability and oxygen tolerance.

1,2-Trans-Selective Synthesis of Glycosyl Boranophosphates and Their Utility as Building Blocks for the Synthesis of Phosphodiester-Linked Disaccharides

2010 ◽  
Vol 75 (7) ◽  
pp. 2147-2156 ◽  
Author(s):  
Kazuki Sato ◽  
Natsuhisa Oka ◽  
Shoichi Fujita ◽  
Fumiko Matsumura ◽  
Takeshi Wada
Keyword(s):  
Building Blocks ◽  
Selective Synthesis

2,3-Dihalo-1-propenes as Building Blocks in Cu(I)-Catalyzed Domino Reactions: Efficient and Selective Synthesis of Furans

2014 ◽  
Vol 16 (18) ◽  
pp. 4862-4865 ◽  
Author(s):  
Dietmar Schmidt ◽  
Chandi C. Malakar ◽  
Uwe Beifuss
Keyword(s):  
Building Blocks ◽  
Selective Synthesis ◽  
Domino Reactions

scholarly journals The synthesis of the 2,3-difluorobutan-1,4-diol diastereomers

2017 ◽  
Vol 13 ◽  
pp. 2883-2887 ◽  
Author(s):  
Robert Szpera ◽  
Nadia Kovalenko ◽  
Kalaiselvi Natarajan ◽  
Nina Paillard ◽  
Bruno Linclau
Keyword(s):  
Building Blocks ◽  
Diastereoselective Synthesis ◽  
Fluorinated Building Blocks ◽  
Epoxide Opening

The diastereoselective synthesis of fluorinated building blocks that contain chiral fluorine substituents is of interest. Here we describe optimisation efforts in the synthesis of anti-2,3-difluorobutane-1,4-diol, as well as the synthesis of the corresponding syn-diastereomer. Both targets were synthesised using an epoxide opening strategy.

ChemInform Abstract: 1,2-trans-Selective Synthesis of Glycosyl Boranophosphates and Their Utility as Building Blocks for the Synthesis of Phosphodiester-Linked Disaccharides.

ChemInform ◽  
2010 ◽  
Vol 41 (30) ◽  
pp. no-no
Author(s):  
Kazuki Sato ◽  
Natsuhisa Oka ◽  
Shoichi Fujita ◽  
Fumiko Matsumura ◽  
Takeshi Wada
Keyword(s):  
Building Blocks ◽  
Selective Synthesis

scholarly journals Highly selective synthesis of d-amino acids via stereoinversion of corresponding counterpart by an in vivo cascade cell factory

2021 ◽  
Vol 20 (1) ◽  
Author(s):  
Dan-Ping Zhang ◽  
Xiao-Ran Jing ◽  
Lun-Jie Wu ◽  
An-Wen Fan ◽  
Yao Nie ◽  
...  
Keyword(s):  
Escherichia Coli ◽  
Amino Acids ◽  
Catalytic Efficiency ◽  
Building Blocks ◽  
Cell Factory ◽  
Selective Synthesis ◽  
Whole Cell ◽  
Whole Cell Biocatalyst ◽  
Cascade Biocatalysis

Abstract Background d-Amino acids are increasingly used as building blocks to produce pharmaceuticals and fine chemicals. However, establishing a universal biocatalyst for the general synthesis of d-amino acids from cheap and readily available precursors with few by-products is challenging. In this study, we developed an efficient in vivo biocatalysis system for the synthesis of d-amino acids from l-amino acids by the co-expression of membrane-associated l-amino acid deaminase obtained from Proteus mirabilis (LAAD), meso-diaminopimelate dehydrogenases obtained from Symbiobacterium thermophilum (DAPDH), and formate dehydrogenase obtained from Burkholderia stabilis (FDH), in recombinant Escherichia coli. Results To generate the in vivo cascade system, three strategies were evaluated to regulate enzyme expression levels, including single-plasmid co-expression, double-plasmid co-expression, and double-plasmid MBP-fused co-expression. The double-plasmid MBP-fused co-expression strain Escherichia coli pET-21b-MBP-laad/pET-28a-dapdh-fdh, exhibiting high catalytic efficiency, was selected. Under optimal conditions, 75 mg/mL of E. coli pET-21b-MBP-laad/pET-28a-dapdh-fdh whole-cell biocatalyst asymmetrically catalyzed the stereoinversion of 150 mM l-Phe to d-Phe, with quantitative yields of over 99% ee in 24 h, by the addition of 15 mM NADP+ and 300 mM ammonium formate. In addition, the whole-cell biocatalyst was used to successfully stereoinvert a variety of aromatic and aliphatic l-amino acids to their corresponding d-amino acids. Conclusions The newly constructed in vivo cascade biocatalysis system was effective for the highly selective synthesis of d-amino acids via stereoinversion.

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