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Article
Carane amino alcohols as organocatalysts in asymmetric aldol reaction of isatin with acetone
Carane-derived β-amino alcohols with amino and hydroxy groups at positions 3 and 4 differing in their mutual arrangement and configuration were synthesized. Their application as organocatalysts in the asymmetr...
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Article
Synthetic analogs of phytanic acid and their effect on human hepatic cholesterol esterase in vitro
Ten acyclic isoprenoid fatty acids were synthesized and tested in vitro as possible regulators of the cholesterol/cholesteryl alkanoate ratio in blood serum lipoproteins. Racemic C20 analogs of (3R/S,7R, 11R)-3,7...
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Article
The effects of the nature of catalyst and of the solvent on the stereoselectivity in amine-catalyzed asymmetric synthesis of substituted cyclohexa-1,3-dienes from prenal and monoesters of ylidenemalonic acids
In the amine-catalyzed reactions of prenal with (Z)-5-methyl-2-(methoxycarbonyl)hexa-2,4-dienoic or (Z)-3-phenyl-2-(ethoxycarbonyl)prop-2-enoic acid chiral β-amino alcohols provide for higher enantiomeric purity ...
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Article
Catalytic asymmetric synthesis of polysubstituted cyclohexa-1,3-dienes from β-branched α,β-alkenals
3-Methyl- and 3-phenylbut-2-enal in the presence of (S)-prolinol (0.1 eq.) in benzene or THF react with the acidic monoesters of alkenylidene, and arylmethylidene-, and alkylidenemalonic acids at −10 to +22 °C to...
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Article
Synthesis of polysubstituted 1,3-cyclohexadienes from β-branched α,β-alkenals and monoesters of ylidenemalonic acids
3-Methyl- and 3-phenyl-2-butenal react with monoesters of alkylidene-, alkenylidene-, and arylmethylenemalonic acids in the presence of piperidine as the catalyst to give esters of 4,6-disubstituted 1,3-cycloh...
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Article
Catalytic asymmetric synthesis of 6-substituted derivatives of 1,3-cyclohexadienecarboxylic acid
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Article
Acyclic isoprenoid 1,3-dieneamines in the Diels-Alder reaction
The dieneamines obtained from 3-methyl-2-butenal and citral (Ia) and (Ib, c) enter into [4 + 2]-cycloaddition with monoethyl citrylidenemalonate (II) and prenylidenemalonate (III), respectively, forming the es...
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Article
Mechanism of cyclocondensation of isoprenoid acyclic α,Β-enals with monoethyl malonate under the conditions of the Knoevenagel reaction
It was shown that the formation of the di- and trisubstituted derivatives of 1.3-cyclohexadiene-1-carboxylic acid during the condensation of 3-methyl-2-butenal, citral, and farnesal with monoethyl malonate in ...
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Article
Cyclodimerization of a citral dienamine
The dienamine (a mixture of isomers) obtained from citral and diethylamine is converted to a mixture of citral anhydro cyclodimers by the action of weak proton-donor agents. The principal reaction product corr...
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Article
Synthesis of derivatives of polyprenylacetic acids and related isoprenoids (review)
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Article
Formation of derivatives of 1,3-cyclohexadienecarboxylic acid from acyclic isoprenoid α,Β-enals and monoethyl malonate by the Knoevenagel reaction
In the presence of piperidine in toluene (110‡C, 40 min) the reaction of 3-methyl-2-butenal, citral, or farnesal with monoethyl malonate gives, along with the esters of the respective alkenylideneacetic acids,...
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Article
Acyclic isoprenoid α,Β-enals in the Doebner and Knoevenagel reactions with monoethyl malonate
When acyclic isoprenoid α,Β-enals are condensed with monoethyl malonate in the presence of pyridine or 4-dimethylaminopyridine (Doebner reaction) or piperidine (Knoevenagel reaction), beside the esters of 2,4-...
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Article
Biologically active derivatives of polyprenylacetic acids and related compounds (review)
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Article
Improved method for the isolation of geranyl esters of (4E/Z,8E)- and (4E/Z,8Z)-farnesylacetic acid