August 2010
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40 Reads
ChemInform
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August 2010
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40 Reads
ChemInform
June 2010
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11 Reads
ChemInform
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
June 2010
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7 Reads
ChemInform
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
April 2010
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50 Reads
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11 Citations
The one-pot three-component reaction of an aryl aldehyde, an arylamine, and a trialkylborane in the presence of hydrogen peroxide afforded the alkylated arylamines 1 in good yields via oxidized imine–borane complexes. In addition, the versatility of our procedure has been confirmed by the use of enolizable aldehydes, alkylic amines, and cyclic imines.
February 2010
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53 Reads
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17 Citations
The total synthesis of the natural compound (8S*,14S*)-8-(4′-hydroxybenzyl)-2,3-dimethoxyberbin-10-ol and its C-8 epimer has been conveniently developed by making use of the diastereoselective Stevens rearrangement of the corresponding N-(arylmethyl)berbinium salts as the key step.
January 2008
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35 Reads
ChemInform
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
September 2007
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44 Reads
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8 Citations
The reaction of an aldimine with dicyclohexylboron chloride in the presence of hydrogen peroxide gives N-[cyclohexyl(aryl)methyl]arylamines 2 in good yields via oxidized imine–borane complexes. The amines can also be obtained by a three-component reaction involving an arenecarbaldehyde, an arylamine and a dialkylchloroborane reagent. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
February 2006
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77 Reads
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4 Citations
An improved synthetic approach to protopines based on the sequential Hofmann elimination, hydroboration and oxidation of N-(arylmethyl)berbinium salts has been designed. By using berberine chloride as the starting material, this sequence of reactions has provided two new nonnatural protopines, N-benzyl-N-nordihydroallocriptopine and N-(p-methoxybenzyl)-N-nordihydroallocriptopine and the natural allocriptopine. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
September 2005
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73 Reads
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11 Citations
Phytochemical Analysis
Six cularine alkaloids, cularicine, O-methylcularicine, celtisine, cularidine, cularine and celtine, three isocularine alkaloids, sarcophylline, sarcocapnine and sarcocapnidine, and five non-cularine alkaloids, glaucine, protopine, ribasine, dihydrosanguinarine and chelidonine, were identified and quantified by GC-MS in nine taxa of the genus Sarcocapnos (Fumariaceae). The chemotaxonomic significance of the results is discussed. Copyright © 2005 John Wiley & Sons, Ltd.
September 2005
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249 Reads
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19 Citations
Phytochemical Analysis
Six cularine alkaloids, cularicine, O-methylcularicine, celtisine, cularidine, cularine and celtine, three isocularine alkaloids, sarcophylline, sarcocapnine and sarcocapnidine, and five non-cularine alkaloids, glaucine, protopine, ribasine, dihydrosanguinarine and chelidonine, were identified and quantified by GC-MS in nine taxa of the genus Sarcocapnos (Fumariaceae). The chemotaxonomic significance of the results is discussed.
... Wu et al. identified and quantified the intracellular concentration of protopine in HL-7702 cells by liquid chromatography-tandem mass spectrometry (LC-MS/MS) [14]. Protopine can also be identified and quantified by GC-MS and TLC/GC-MS methods [15,16]. Compared to HPLC-MS or HPLC-NMR, TLC/GC-MS has the advantages of short identification time, low cost of separation, and simple operation. ...
September 2005
Phytochemical Analysis
... In contrast with other related alkaloids that contain the quinolizidine moiety (e.g. berbines), 25 inversion at the N bridgehead of the starting material is unlikely in phenanthroquinolizidines and the adjacent methyl group should stabilize the trans isomer. It is generally assumed that, either by formation of an iminium ion or via recombination of radical pairs in the solvent-cage, 26 the Stevens rearrangement is suprafacial. ...
June 2002
Tetrahedron
... Establishment of the requisite cis-diol 146 from this transformation was attributed to the chelation of cationic samarium with the two carbonyl functionality before the coupling took place. The synthesis of (+)-alopecuridineÁTFA (147) was completed in another three steps from 146, and the synthetic (+)-alopecuridine could be converted to (+)-sieboldine A (139) Using 157 as a starting material, the total synthesis of (À)-farnesiferol C was accomplished in 7 steps. ...
February 2010
... According to the general procedure. 3 According to the general procedure. Yellow oil (49.8 mg, 51% ...
September 2007
... To appraise the applicability of the procedure, we extended the study of the one-pot alkylation reaction to enantiomerically pure amines. Chiral amines (1S)-1-phenylethanamine (13) and L-valine methyl ester (14) were made to react with p-anisaldehyde (12) and Et 3 B (Scheme 4), in dichloromethane at 20°C. ...
April 2010
... Recently, Cabedo et al. 118 To explore the role of the 1-benzyl group in the tetrahydroisoquinolines, Andreu et al. 119 prepared compounds with a cyclohexylmethyl group at the C-1 position to replace the benzyl substituent (115a,b, 116; Figure 9). These novel compounds, like their benzyl congeners, retained substantial D 2 receptor binding. ...
December 2002
Tetrahedron
... In addition, the reaction quantum yield of rearranged products is strongly influenced by solvent polarity as well as by the presence of electron donor or acceptor in the aromatic moiety. 19,27,32,44,45 Scheme 1. General scheme of Photo-Fries rearrangement. ...
February 1995
Tetrahedron Letters
... The total synthesis of these alkaloids typically involves isoquinoline synthesis methods, such as Bischler-Napieralski cyclization, 6) Pictet-Spengler cyclization, 7,8) intramolecular N-alkylation, 6) intramolecular hydroamination, 7) and others. [9][10][11][12] Alternative synthetic approaches include Stevens rearrangement for the installation of C8-substituents. 13) The relative stereochemistry between H8 and H14 is trans in javaberine A (1), theoneberine (2), and O-methylcorytenchirine (3), whereas a cis relationship is observed in coralydine (4). ...
November 2004
... The family Fumariaceae is composed of about 600 species from worldwide spread genera Fumaria, Corydalis, Rupicapnos, Sarcocapnos, Ceratocapnos and Platycapnos [1,2,3,4]. Genus Corydalis is represented by 470 plant species [4,5]. This genus comprises only four taxa in Bulgaria (Corydalis solida (L.) Swartz., C. marschalliana (Willd.) ...
September 2005
Phytochemical Analysis