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Keywords = DIBAL-H

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11 pages, 1261 KB  
Article
Synthesis of Demissidine Analogues from Tigogenin via Imine Intermediates
by Agnieszka Wojtkielewicz, Urszula Kiełczewska, Aneta Baj and Jacek W. Morzycki
Int. J. Mol. Sci. 2021, 22(19), 10879; https://doi.org/10.3390/ijms221910879 - 8 Oct 2021
Cited by 3 | Viewed by 2999
Abstract
A five-step transformation of a spiroketal side chain of tigogenin into an indolizidine system present in solanidane alkaloids such as demissidine and solanidine was elaborated. The key intermediate in the synthesis was spiroimine 3 readily obtained from tigogenin by its RuO4 oxidation [...] Read more.
A five-step transformation of a spiroketal side chain of tigogenin into an indolizidine system present in solanidane alkaloids such as demissidine and solanidine was elaborated. The key intermediate in the synthesis was spiroimine 3 readily obtained from tigogenin by its RuO4 oxidation to 5,6-dihydrokryptogenin followed by amination with aluminum amide generated in situ from DIBAlH and ammonium chloride. The mild reduction of spiroimine to a 26-hydroxy-dihydropyrrole derivative and subsequent mesylation resulted in the formation of 25-epidemissidinium salt or 23-sulfone depending on reaction conditions. Full article
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10 pages, 1839 KB  
Article
C-N Bond Formation by Consecutive Continuous-Flow Reductions towards A Medicinally Relevant Piperazine Derivative
by Zsolt Fülöp, Péter Bana, István Greiner and János Éles
Molecules 2021, 26(7), 2040; https://doi.org/10.3390/molecules26072040 - 2 Apr 2021
Cited by 2 | Viewed by 3881
Abstract
A new, continuous-flow consecutive reduction method was developed for the C-N bond formation in the synthesis of the key intermediate of the antipsychotic drug cariprazine. The two-step procedure consists of a DIBAL-H mediated selective ester reduction conducted in a novel, miniature alternating diameter [...] Read more.
A new, continuous-flow consecutive reduction method was developed for the C-N bond formation in the synthesis of the key intermediate of the antipsychotic drug cariprazine. The two-step procedure consists of a DIBAL-H mediated selective ester reduction conducted in a novel, miniature alternating diameter reactor, followed by reductive amination using catalytic hydrogenation on 5% Pt/C. The connection of the optimized modules was accomplished using an at-line extraction to prevent precipitation of the aluminum salt byproducts. Full article
(This article belongs to the Special Issue Advances in Flow Chemistry)
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4 pages, 373 KB  
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(E)-2-((4R,5R)-5-((Benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-ene-1,4-diol
by Carlos R. Carreras, Celina E. García, Víctor S. Martín, Carlos E. Tonn, David Díaz Díaz and Juan Pedro Ceñal
Molbank 2010, 2010(2), M676; https://doi.org/10.3390/M676 - 19 Apr 2010
Cited by 1 | Viewed by 9313
Abstract
The synthesis of (E)-2-((4R,5R)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-ene-1,4-diol by a one-step reduction of the appropriate 2-substituted butenolide is reported. Product characterization was carried out by IR, 1H NMR, 13C NMR, MS, elemental analysis and optical rotation. Full article
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