Chemistry Of Alkaloids Research Articles

Isolation and Chemistry of Alkaloids from Plants of the Papaveraceae1

From Fumaria scbrammii (Ascherson) Veeen. collected near Varna (Bulgaria), a mixture of alkaloids (0.27 %) was isolated. It contained the major alkaloid protopine together with parfumine, adlumidiceine, adlumiceine, adlumidiceine and adlumiceine enol lactones, cryptopine, dihydrofumariline, fumancine, tetrahydrocoptisine, and coptisine. The presence of the alkaloids sanguinarine and chelerythrine was revealed by TLC. The alkaloids dihydrofumariline and adlumiceine enol lactone have not been isolated previously from natural sources. The spectral data for adlumiceine and dihydrofumariline are given.

Synthesis of racemic 3‐hydroxy‐N‐methyl‐6‐oxomorphinan (Chemistry of opium alkaloids, Part XIV)

AbstractThe preparation of racemic 3‐hydroxy‐N‐methyl‐6‐oxomorphinan (5) by acid‐catalysed cyclization of 1‐(4‐hydroxybenzyl)‐1,2,3,4,5,8‐hexahydro‐6‐methoxy‐2‐methylisoquinoline (4) and its 4′‐methyl ether 6 is described. The corresponding N‐formyl derivatives did not give the desired cyclization.

Oxidation of (‐)‐2‐bromo‐3‐hydroxy‐N‐methyl‐6‐oxomorphinan with Fremy's salt. An unprecedented 2,4‐shift of the bromo substituent. (Chemistry of opium alkaloids, Part XIII)

Abstract(‐)‐3‐Hydroxy‐N‐methyl‐6‐oxomorphinan (6a) and its (‐)‐2‐bromo derivative (6b) were converted into (‐)‐2,3‐dihydroxy‐N‐methyl‐6‐oxomorphinan (8a) and its (‐)‐4‐bromo derivative (8b), respectively, by oxidation with Fremy's salt to the ortho‐quinones, followed by reduction. Methylation of 8a and 8b gave the corresponding methyl ethers 9a and 9b. Catalytic hydrogenolysis of 8b and 9b gave 8a and 9a, respectively. The structure of (‐)‐2,3‐dimethoxy‐N‐methyl‐6‐oxomorphinan (9a) was confirmed by total synthesis, and that of (‐)‐4‐bromo‐2,3‐dimethoxy‐N‐methyl‐6‐oxomorphinan (9b) by single‐crystal X‐ray analysis.The model compound 2‐bromo‐4,5‐dimethylphenol (15) gave, analogously, 3‐bromo‐4,5‐dimethyl‐pyrocatechol (16).

Recent Advances in the Chemistry of Berbine Alkaloids

Recent Advances in the Chemistry of Berbine Alkaloids

Developments in the Chemistry of Diterpenoid Alkaloids

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTDevelopments in the Chemistry of Diterpenoid AlkaloidsS. William Pelletier and Naresh V. ModyCite this: J. Nat. Prod. 1980, 43, 1, 41–71Publication Date (Print):January 1, 1980Publication History Published online1 July 2004Published inissue 1 January 1980https://doi.org/10.1021/np50007a003RIGHTS & PERMISSIONSArticle Views314Altmetric-Citations22LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (1 MB) Get e-Alerts Get e-Alerts

Main stages in the development of domestic alkaloid chemistry

The following are considered: 1) the study of alkaloids in Russia before the Great October Socialist Revolution. 2) The development of industry and of scientific investigations in the field of alkaloid chemistry at the end of the XIXth and the beginning of the XXth centuries and the influence of social factors on the development of this part of knowledge. 3) The work of Academician A. P. Orekhov and his school, which opened up a new direction in the development of alkaloid chemistry. 4) The achievements of the modern school of alkaloid investigators in the USSR.

Isolation and Chemistry of Alkaloids from Plants of the Papaveraceae. LXXV1

Isolation and Chemistry of Alkaloids from Plants of the Papaveraceae. LXXV¹

Isolation and Chemistry of the Alkaloids from Plants of the Papaveraceae. LXXIII1: Isolation and Identification of Alkaloids from Corydalis lutea (L.) DC.2

Isolation and Chemistry of the Alkaloids from Plants of the Papaveraceae. LXXIII¹: Isolation and Identification of Alkaloids from Corydalis lutea (L.) DC.²

On the closure of the 4,5‐oxygen bridge in morphinans 1H and 13C NMR spectroscopy of brominated intermediates. (Chemistry of opium alkaloids, Part IX)

Abstract1H and 13C Nuclear magnetic resonance spectra of brominated dihydrothebainones, needed for the closure of the oxygen bridge of morphinans to form morphine derivatives, were studied. Bromination of (‐)‐dihydrothebainone (1) yielded successively 1‐bromo‐, 1,7α‐dibromo‐, and 1,5β,7α‐tribromo‐dihydrothebainone (2,3,4). 1‐Bromo‐O4‐methyldihydrothebainone (12) gave, after bromination, a stable crystalline l,5β,7α‐tribromo derivative (15). A 5β,7α‐dibromo derivative (9) was formed also starting with l‐methyldihydrothebainone (7).Closure of the oxygen bridge in 1,5β,7α‐tribromodihydrothebainone (4) in boiling ethanol, yields an equilibrium mixture of 1,7β‐ and 1,7β‐dibromodihydrothebainone (5:6, ∼ 35 : 65). 5β,7α‐Dibromo‐l‐methyldihydrothebainone (9) gave the same result.13C NMR spectra of the model compounds cyclohexanone, 2‐bromo‐, 2,2‐dibromo‐, cis‐ and trans‐2,6‐dibromo‐cyclohexanone were studied.

Chemistry of opium alkaloids : VIII. Separation of opium alkaloids and related compounds by ion-pair high-performance liquid chromatography

Chemistry of opium alkaloids : VIII. Separation of opium alkaloids and related compounds by ion-pair high-performance liquid chromatography

ChemInform Abstract: Chemistry of Opium Alkaloids. Part 4. Synthesis of Racemic and of (+)‐ and (‐)‐1‐ Methyldihydrothebainone.

AbstractDas aus den Komponenten (I) und (II) erhältliche Amid (III) wird nach Bischler‐Napieralski zum Dihydroisochinolin (IV) cyclisiert, dessen Birch‐Reduktion die racemische Verbindung (Va) liefert.

A practical technique for laboratory Birch reductions (Chemistry of opium alkaloids, Part VI)

AbstractA practical technique and a simple apparatus are described, which makes possible various ways of carrying out Birch reductions on a (0.1−10 g)‐scale. Examples of reductions of 1‐benzylisoquinolines and β‐nitrostyrenes are discussed. Reaction of 1,2,3,4,5,8‐hexahydro‐1‐(3,5‐dihydroxy‐4‐methoxybenzyl)‐6‐methoxyisoquinoline (2b) with acetone yielded a hexahydrodimethylprotoberberine (3).

Synthesis of racemic and of (+)‐ and (‐)‐1‐methyldihydrothebainone. (Chemistry of opium alkaloids, Part IV)

AbstractRacemic 1‐(5‐benzyloxy‐4‐methoxy‐2‐methylbenzyl)‐1,2,3,4‐tetrahydro‐6‐methoxyisoquinoline (rac. 3) was synthesized (Scheme 1). Resolution with (+)‐ and with (‐)‐6,6′‐dinitrobiphenyl‐2,2′‐dicarboxylic acid yielded (‐)‐ and (+)‐3, respectively. By a Birch reduction, followed by N‐formylation, and by acid‐catalysed cyclization, we obtained in high yield racemic, (‐)‐, and (+)‐N‐formyl‐1‐methylnordihydrothebainone (6), respectively. In two ways, by direct reduction and by deformylation followed by reductive methylation, 6 could be converted selectively into racemic, and (‐)‐, and (+)‐1‐methyldihydrothebainone (7).Synthetic (‐)‐7 was found to be identical with (‐)‐1‐methyldihydrothebainone prepared from natural material. This completes the proof of the structure.The optical rotatory dispersion spectra are discussed.

Conversion of (‐)‐dihydrocodeinone into (‐)‐1‐methyldihydrocodeinone, (‐)‐1‐methyldihydrocodeine and (‐)‐1‐methyldihydrothebainone. (Chemistry of opium alkaloids, Part V)

AbstractChloromethylation of (‐)‐dihydrocodeinone (1) followed by reduction with zinc yielded, via 2, (‐)‐1‐methyldihydrocodeinone (3). Further reduction afforded (‐)‐1‐methyldihydrothebainone (4). The latter compound proved to be identical with (‐)‐1‐methyldihydrothebainone prepared by total synthesis. This proves position 1 of the chloromethylation and, in consequence, of the methyl group.Compound 3 could also be reduced catalytically to (‐)‐1‐methyldihydrocodeine (5).

Alkaloids of callus tissues and redifferentiated plantlets in the papaveraceae

The callus tissues from 11 representative species of the Papaveraceae and the redifferentiated plantlets from four species were successfully derived and maintained. The alkaloids in the callus tissues and redifferentiated plantlets were examined in comparison with those of the original plants. All the callus tissues are similar in their alkaloid chemistry and contain benzophenanthridine, protopine and aporphine type alkaloids. By contrast, the plantlets have a more specific alkaloid pattern, being similar in content to the original plants.

Structure elucidation and chemistry of Catharanthus alkaloids. XXX. Isolation and structure elucidation of vincarodine.

Structure elucidation and chemistry of Catharanthus alkaloids. XXX. Isolation and structure elucidation of vincarodine.

Isolation and chemistry of papaver alkaloids. 58. Isolation and identification of alkaloids from Papaver urbanianum Fedde

Aus der Gattung Papaver urbanianum Fed de (Papaveraceae: Sektion Miltantha Bernh.) wurde ein Alkaloidgemisch (0,30 %) isoliert. Präparative Chromatographie ergab die Alkaloide 6a,7–Didehydroaporhein, (+)–Aporhein, (–)–Mecambrin, (–)–Armepavin, (–)–N–Norarmepavin, Muramin, N–Methyl–6,7–dimethoxytetrahydroisochinolon–(1) und Palmatin. Diinnschichtchromatographisch wurde die Gegenwart der Alkaloide Protopin und Papaverrubin B nachgewiesen. Die Alkaloide (–)–N–Norarmepavin und N–Methyl–6,7–dimethoxytetrahydroisochinolon–(1) sind in den Arten der Familie Papaveraceae bisher nicht gefunden worden. Die gewonnenen Ergebnisse ergänzen die hinsichtlich der Zureihung der Arten zur Sektion Miltantha Bernh. gezogenen chemotaxonomischen Schlüsse.

Soviet advances in the development of the chemistry of the alkaloids

Soviet advances in the development of the chemistry of the alkaloids

Fire ant venoms: comparative analyses of alkaloidal components.

The chemistry of the venom alkaloids of Solenopsis geminata, S. xyloni and the red and black forms of S. saevissima was investigated. All four forms have a venom composition characterized by the presence of various 2,6-disubstituted piperidines in amounts distinctive of the form. The alkaloids of the red and black forms mainly contain an alkenyl group in position 6 and a trans configuration of the substituents on the piperidine ring, while those of the two indigenous species of North American fire ants contain alkyl substituents which are both cis and trans on the ring. In addition, the venom of S. xyloni contains detectable amounts of 2-methyl-6- n -undecyl- Δ 1,2 -piperideine, a possible precursor of certain of these alkaloids.

The Chemistry of the Isoquinoline Alkaloids

The Chemistry of the Isoquinoline Alkaloids