- (S)-(-)-α-Methylbenzylamine as chiral auxiliary in the synthesis of (+)-lortalamine
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(+)-Lortalamine was synthesised using (S)-(-)-α-methylbenzylamine as a chiral auxiliary. The stereochemistry of an intermediate compound was established on the basis of X-ray crystallography, allowing unambiguous assignment of the absolute configuration.
- Pawlowska, Jolanta,Krawczyk, Krzysztof K.,Wojtasiewicz, Krystyna,Maurin, Jan K.,Czarnocki, Zbigniew
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- COMPOSITIONS AND METHODS FOR TREATING MALARIA
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Disclosed are methods of treating malaria with tetrahydrobenzonaphtyridine carboxanilide (TBN) derivatives and related pyrrolinones and hydrolysis products thereof. These compounds are active against Plasmodium falciparum strains that are resistant to multiple drugs currently on the market. The present invention further relates to novel compounds and pharmaceutical compositions comprising such compounds.
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Page/Page column 78
(2021/08/27)
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- BENZENESULFONAMIDE COMPOUNDS AND THEIR USE AS THERAPEUTIC AGENTS
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This invention is directed to benzenesulfonamide compounds, as stereoisomers, enantiomers, tautomers thereof or mixtures thereof; or pharmaceutically acceptable salts, solvates or prodrugs thereof, for the treatment of diseases or conditions associated with voltage-gated sodium channels, such as epilepsy.
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Page/Page column 163-164; 168-169
(2017/12/18)
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- Electrochemical access to 8-(1-phenyl-ethyl)-1,4-dioxa-8-aza-spiro[4.5] decane-7-carbonitrile. Application to the asymmetric syntheses of (+)-myrtine and alkaloid (+)-241D
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The total syntheses of both enantiomers of trans-quinolizidine (+)-myrtine and cis-2,4,6-trisubstituted piperidine alkaloid (+)-241D are reported here. Our approach was based on the N-Boc-directed metalation of enantiopure 4-piperidone (-)-11, which was prepared in four steps from α-amino nitrile 6 through a stereoselective alkylation-reduction decyanation process. α-Amino nitrile 6 was prepared at the anode through electrochemical oxidation of 4-piperidone (+)-5. In our study, α-phenylethylamine (α-PEA) allowed an efficient 1-3 stereoinduction, and an orthogonal cleavage of the N-Boc protecting group in piperidone derivatives was carried out by stirring them in a suspension of SnCl4·(Et2O)2 complex in diethyl ether. When appropriate, the ers were determined by proton and carbon NMR spectroscopy utilizing (+)-tert-butylphenylphosphinothioic acid and (+)-DBTA as chiral solvating agents.
- Vu, Van Ha,Louafi, Fadila,Girard, Nicolas,Marion, Ronan,Roisnel, Thierry,Dorcet, Vincent,Hurvois, Jean-Pierre
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p. 3358 - 3373
(2014/05/06)
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- Synthesis and antihistamine evaluations of novel loratadine analogues
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A series of loratadine analogues containing hydroxyl group and chiral center were synthesized. The effect of the synthesized compounds on the histamine-induced contractions of guinea-pig ileum muscles was studied. In addition, the in vivo asthma-relieving effect of the analogues in the histamine induced asthmatic reaction in guinea-pigs was determined. Most of the compounds exhibited definite H1 antihistamine activity. The S-enantiomers, compounds 2, 4 and 8, are more potent than the R-enantiomers, compounds 1, 3 and 7. Compound 6 was the most active one among the eight synthesized compounds.
- Wang, Yue,Wang, Juan,Lin, Yan,Si-Ma, Li-Feng,Wang, Dong-Hua,Chen, Li-Gong,Liu, Deng-Ke
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p. 4454 - 4456
(2011/09/15)
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- Enantioselective Syntheses of Vinblastine, Leurosidine, Vincovaline, and 20'-epi-Vincovaline
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The binary indole-indoline alkaloids vinblastine (1), leurosidine (13), 20'-epi-vincovaline (14a), and vincovaline (14b) were obtained by coupling of vindoline (3) to the tetracyclic intermediates 7a, 7b or 22a, 22b, followed by reduction and cyclization
- Kuehne, Martin E.,Matson, Patricia A.,Bornmann, William G.
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p. 513 - 528
(2007/10/02)
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- THE (13)C NMR SPECTRA, ISOMERISM, AND CONFORMATIONAL ANALYSIS OF SUBSTITUTED PIPERIDIN-4-ONES
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The (13)C NMR spectra of 15 stereoisomers of 1-mono, 1,2-di, and 1,2,5-trisubstituted piperidin-4-ones were investigated, and the stereochemical orientations of the substituents and the conformation relationships were established.For the series of piperid
- Leshcheva, I. F.,Sergeev, N. M.,Grishina, G. V.,Potapov, V. M.
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p. 1214 - 1225
(2007/10/02)
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- STERIC CONTROL OF THE ASYMMETRIC SYNTHESIS OF N-SUBSTITUTED 2-METHYL-4-PIPERIDONES
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Transmission of the iodomethylate of 1,2-dimethyl-4-piperidone by (S)-sec-butylamine gives 1-(S-sec-butyl)-2S-methyl-4-piperidone in 33percent optical yield while transamination by (S)-1-methyl-2-phenylethylamine gives a 1:1 diastereomeric mixture of 1-(1-methyl-2-phenylethyl)-2-methyl-4-piperidone.The decrease in the optical yield is related to the facile opening of the piperidone ring at the C-N bond with subsequent recyclization.The 13C NMR data indicate that all the diastereomers of the 4-piperidones obtained are in the chair conformation with predominantly equatorial orientation of the methyl group at C(2).The chi ral optical properties were studied and the absolution configurations of the 4-piperidones were established.
- Grishina, G. V.,Potapov, V. M.,Abdulganeeva, S. A.,Korchagina, E. Yu.
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p. 1355 - 1362
(2007/10/02)
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