Stereoselective syntheses and transformations of chiral 1,3-aminoalcohols and 1,3-diols derived from nopinone

Szakonyi, Zsolt; Gonda, Tímea; Ötvös, Sándor B.; Fülöp, Ferenc

doi:10.1016/j.tetasy.2014.06.017

Cited by 29 publications

(32 citation statements)

References 37 publications

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“…These features ensured improved operational safety and simplicity over traditional hydrogenation techniques . Importantly, the flow system furnished an excellent level of control over the most important reaction parameters that determine the product selectivity . A representation of the flow reactor is shown in Figure .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Nontoxic Protoflavone Derivatives through Selective Continuous‐Flow Hydrogenation of the Flavonoid B‐Ring

et al. 2017

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Protoflavones are unique natural flavonoids with a non‐aromatic B‐ring, known for their potent antitumor properties. However, their cytotoxicity represents a strong limitation in the further exploration of their pharmacological potential. In the current study, we sought to selectively saturate the p‐quinol B‐ring of protoapigenone and that of its 1′‐O‐butyl ether, in order to obtain non‐toxic protoflavone analogues expressing the dihydro‐ or tetrahydroprotoflavone structure also occurring in nature. The benefits of a strictly controlled continuous‐flow environment in combination with on‐demand electrolytic H2 gas generation were exploited to suppress undesired side reactions and to safely and selectively yield the desired substances. The obtained tetrahydroprotoflavones were free of the cytotoxicity of their parent compounds, and, even though tetrahydroprotoapigenone 1‐O‐butyl ether showed a weak inhibition of DNA damage response through Chk1, neither compounds influenced the cytotoxicity of doxorubicin either.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Nontoxic Protoflavone Derivatives through Selective Continuous‐Flow Hydrogenation of the Flavonoid B‐Ring

et al. 2017

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“…Similar deprotection was carried out on nopinone‐derived 1,3‐aminoalcohols,12 but with the aim of identifying reaction conditions ensuring the selective removal of only one of two benzyl groups (Scheme ).…”

Section: Cf Hydrogenationmentioning

confidence: 99%

Harnessing the Versatility of Continuous-Flow Processes: Selective and Efficient Reactions

Mándity

Ötvös

Szőlősi

et al. 2016

The Chemical Record

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There is a great need for effective transformations and a broad range of novel chemical entities. Continuous-flow (CF) approaches are of considerable current interest: highly efficient and selective reactions can be performed in CF reactors. The reaction setup of CF reactors offers a wide variety of possible points where versatility can be introduced. This article presents a number of selective and highly efficient gas-liquid-solid and liquid-solid reactions involving a range of reagents and immobilized catalysts. Enantioselective transformations through catalytic hydrogenation and organocatalytic reactions are included, and isotopically labelled compounds and pharmaceutically relevant 1,2,3-triazoles are synthesized in CF reactors. Importantly, the catalyst bed can be changed to a solid-phase peptide synthesis resin, with which peptide synthesis can be performed with the utilization of only 1.5 equivalents of the amino acid.

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“…Synthesis of the novel β-amino-N-hemiacetal 24{1,1}. usefulness of its structural parents γ-aminoalcohols, [43][44][45][46][47] we decided to explore in more detail, reproducibility and scope of this process. Thus, a chemset of diversely substituted secondary amines 19{1-21} and activated alkenes 10{1,3-4} was evaluated under the established reaction conditions.…”

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Recent contributions to the Diversity-Oriented Synthesis (DOS) mediated by iminium ions through multicomponent Mannich-type reactions

Abonı́a¹,

Castillo²,

Kotali³

2017

Arkivoc

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This short account summarizes the most recent contributions of the author and his collaborators to the Diversity Oriented Synthesis (DOS) mediated, at least in a step of the process, by Mannich-type reactions (MTR) and using formaldehyde as common starting material in all cases. Through this strategy, diverse nitrogen-containing acyclic and heterocyclic systems were synthesized, whether in straightforward or multicomponent approaches.

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Stereoselective syntheses and transformations of chiral 1,3-aminoalcohols and 1,3-diols derived from nopinone

Cited by 29 publications

References 37 publications

Synthesis of Nontoxic Protoflavone Derivatives through Selective Continuous‐Flow Hydrogenation of the Flavonoid B‐Ring

Synthesis of Nontoxic Protoflavone Derivatives through Selective Continuous‐Flow Hydrogenation of the Flavonoid B‐Ring

Harnessing the Versatility of Continuous-Flow Processes: Selective and Efficient Reactions

Recent contributions to the Diversity-Oriented Synthesis (DOS) mediated by iminium ions through multicomponent Mannich-type reactions

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