Commercial Scale Process of Galanthamine Hydrobromide Involving Luche Reduction: Galanthamine Process Involving Regioselective 1,2-Reduction of α,β-Unsaturated Ketone

2013 ◽  
Vol 17 (3) ◽  
pp. 406-412 ◽  
Author(s):  
Ganala Naga Trinadhachari ◽  
Anand Gopalkrishna Kamat ◽  
Koilpillai Joseph Prabahar ◽  
Vijay Kumar Handa ◽  
Kukunuri Naga Venkata Satya Srinu ◽  
...  
2016 ◽  
Vol 12 (8) ◽  
pp. 311-317
Author(s):  
Kamelia El-Mahdy

Thiazolopyrimidine 2 was obtained from the reaction of dihydropyrimidinone with chloroacetic acid and benzaldehyde. Thiazolopyrimidine 2 containing an α,β-unsaturated ketonic function [-CH=CH-CO-] has been used as a component of Michael addition with an equimolar amount of dinucleophiles to give a series of novel tetracyclic pyrimidine derivatives. Treatment of thiazolopyrimidine 2 with uracil, aminotriazole, cyanoacetic acid hydrazide, o-phenylenediamine or diaminopyridine afforded the corresponding pyridopyrimidine, triazolopyrimidine, pyrazolone, benzodiazepine and triazepine derivative, respectively. The detailed synthesis, spectroscopic data, and antitumor activity for synthesized compounds were reported.


2016 ◽  
Author(s):  
Owain Tucker ◽  
Lilian Gray ◽  
Wilfried Maas ◽  
Simon O'Brien
Keyword(s):  

2019 ◽  
Author(s):  
Nobutaka Fujieda ◽  
Miho Yuasa ◽  
Yosuke Nishikawa ◽  
Genji Kurisu ◽  
Shinobu Itoh ◽  
...  

Cupin superfamily proteins (TM1459) work as a macromolecular ligand framework with a double-stranded beta-barrel structure ligating to a Cu ion through histidine side chains. Variegating the first coordination sphere of TM1459 revealed that H52A and H54A/H58A mutants effectively catalyzed the diastereo- and enantio-selective Michael addition reaction of nitroalkanes to an α,β-unsaturated ketone. Moreover, in silico substrate docking signified C106N and F104W single-point mutations, which inverted the diastereoselectivity of H52A and further improved the stereoselectivity of H54A/H58A, respectively.


Organics ◽  
2021 ◽  
Vol 2 (1) ◽  
pp. 38-49
Author(s):  
Lakhdar Benhamed ◽  
Sidi Mohamed Mekelleche ◽  
Wafaa Benchouk

Experimentally, a reversal of chemoselectivity has been observed in catalyzed Diels–Alder reactions of α,β-unsaturated aldehydes (e.g., (2E)-but-2-enal) and ketones (e.g., 2-hexen-4-one) with cyclopentadiene. Indeed, using the triflimidic Brønsted acid Tf2NH as catalyst, the reaction gave a Diels–Alder adduct derived from α,β-unsaturated ketone as a major product. On the other hand, the use of tris(pentafluorophenyl)borane B(C6F5)3 bulky Lewis acid as catalyst gave mainly the cycloadduct of α,β-unsaturated aldehyde as a major product. Our aim in the present work is to put in evidence the role of the catalyst in the reversal of the chemoselectivity of the catalyzed Diels–Alder reactions of (2E)-but-2-enal and 2-Hexen-4-one with cyclopentadiene. The calculations were performed at the ωB97XD/6-311G(d,p) level of theory and the solvent effects of dichloromethane were taken into account using the PCM solvation model. The obtained results are in good agreement with experimental outcomes.


Author(s):  
John M. Pollock ◽  
Kerry Miner ◽  
Nathan Buzzell ◽  
Michael Schofield ◽  
Nathan Hawkins ◽  
...  

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