Optically active juvenoids derived from 2-substituted cyclopentanol and their biological activity on Tenebrio molitor

Rejzek, Martin; Wimmer, Zdeněk; Zarevúcká, Marie; Kuldová, Jelena; Šaman, David; Vacek, Miroslav

doi:10.1016/s0957-4166(98)00369-3

Cited by 10 publications

(4 citation statements)

References 15 publications

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“…Additionally, reduction of 2 g with Pd/C followed by separation using preparative column chromatography, allows for a fully hydrogenated product (1 R ,2 R )‐ 4 to be obtained with 90 % ee and 60 % isolated yield. This chiral cyclopentanol is a precursor of juvenile hormone analogues (Scheme 3III) [1e] . The C=C unsaturated bond in the product can also be oxidized by m ‐CPBA to obtain chiral cyclopentanol with β,γ‐epoxy structure 5 (Scheme 3IV).…”

Section: Resultsmentioning

confidence: 99%

Copper‐Catalyzed Chemoselective Asymmetric Hydrogenation of C=O Bonds of Exocyclic α,β‐Unsaturated Pentanones

et al. 2023

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A highly chemoselective earth‐abundant transition metal copper catalyzed asymmetric hydrogenation of C=O bonds of exocyclic α,β‐unsaturated pentanones was realized using H2. The desired products were obtained with up to 99 % yield and 96 % ee (enantiomeric excess) (99 % ee, after recrystallization). The corresponding chiral exocyclic allylic pentanol products can be converted into several bioactive molecules. The hydrogenation mechanism was investigated via deuterium‐labelling experiments and control experiments, which indicate that the keto‐enol isomerization rate of the substrate is faster than that of the hydrogenation and also show that the Cu−H complex can only catalyze chemoselectively the asymmetric reduction of the carbonyl group. Computational results indicate that the multiple attractive dispersion interactions (MADI effect) between the catalyst with bulky substituents and substrate play important roles which stabilize the transition states and reduce the generation of by‐products.

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Section: Resultsmentioning

confidence: 99%

Copper‐Catalyzed Chemoselective Asymmetric Hydrogenation of C=O Bonds of Exocyclic α,β‐Unsaturated Pentanones

et al. 2023

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“…Those compounds are general precursors of a series of insect juvenile hormone bioanalogs, we have been investigating for many years [15,[86][87][88][89][90][91][92][93][94][95][96][97][98][99][100][101]. Lipase-catalyzed resolution processes (Scheme 7) enable in principle preparation of all possible stereoisomers of 2-(4-alkoxybenzyl)cycloalkan-1-ols.…”

Section: Lipase-mediated Resolution Of Racemic Substrates: Synthesis mentioning

confidence: 99%

“…However, lower enantiomeric purity of the unreacted substrate, and the yields rarely exceeding 40% (i.e., 80% conversion) still creates important limitation against selecting this enzymic procedure as general approach in the synthesis of all possible stereoisomers of 2-(4-alkoxybenzyl)cycloalkan-1-ols. More details on our results can be found the respective original papers [15,[86][87][88][89][90][91][92][93][94][95][96][97][98][99][100][101]. Lipase-catalyzed hydrolysis was performed in aqueous media, because this environment is close to the natural environment in which hydrolytic processes are realized by nature itself.…”

Section: Lipase-mediated Resolution Of Racemic Substrates: Synthesis mentioning

confidence: 99%

Selected chiral alcohols: Enzymic resolution and reduction of convenient substrates

Jurček

Wimmerová

Wimmer

2008

Coordination Chemistry Reviews

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“…A Czech group uses both isolated enzymes and whole cells to the preparation of analogues of insect juvenile hormones [29][30]. A Czech group uses both isolated enzymes and whole cells to the preparation of analogues of insect juvenile hormones [29][30].…”

Section: Isolated Enzymesmentioning

confidence: 99%

Alcohol and 1,2-Diol Dehydrogenases: Synthetic Use in the Preparation of Chiral Alcohols by Carbonyl Reduction

Sello¹,

Orsini

2006

MROC

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Chiral alcohols are useful intermediates and auxiliaries in organic synthesis. Their preparation in enantiopure form is consequently of very high interest. Among the different enzymatic procedures, the use of dehydrogenase activities can be considered as the most attractive alternative. These enzymes can fruitfully work in inverse direction as enantioselective reducing agents. We will focus on the use of well-known alcohol dehydrogenases, describing their application in chiral alcohol preparation. A final discussion on the possibility of using these enzymes in either oxidative or reductive direction will be presented.

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Optically active juvenoids derived from 2-substituted cyclopentanol and their biological activity on Tenebrio molitor

Cited by 10 publications

References 15 publications

Copper‐Catalyzed Chemoselective Asymmetric Hydrogenation of C=O Bonds of Exocyclic α,β‐Unsaturated Pentanones

Copper‐Catalyzed Chemoselective Asymmetric Hydrogenation of C=O Bonds of Exocyclic α,β‐Unsaturated Pentanones

Selected chiral alcohols: Enzymic resolution and reduction of convenient substrates

Alcohol and 1,2-Diol Dehydrogenases: Synthetic Use in the Preparation of Chiral Alcohols by Carbonyl Reduction

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