Topic
Brucine
About: Brucine is a research topic. Over the lifetime, 586 publications have been published within this topic receiving 6866 citations. The topic is also known as: 10,11-dimethoxy strychnine.
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11 citations
TL;DR: In this article, the stereoisomers of monocrotalic acid have been synthesized and their stereochemistry was assigned respectively as S- and R-configuration by correlation to the known (R)-(−)-2-phenylpropanoic acid.
Abstract: All stereoisomers (3a, b–6a, b) of monocrotalic acid have been synthesized. Methylation of (±)-cis-2,3,4-trimethyl-2-pentenedioic acid with diazomethane followed by cis-hydroxylation with potassium permanganate afforded two epimeric γ-lactone esters in a ratio of ca. 1:5. These esters were then hydrolyzed with dilute hydrochloric acid to the corresponding acids, (±)-3 and racemic monocrotalic acid (4). Optical resolution of (±)-3 with brucine afforded 3a (2R,3R,4S) and 3b (2S,3S,4R). The racemic monocrotalic acid was also resolved by means of brucine to give natural monocrotalic acid (4a: 2R,3R,4R) and its enantiomer (4b: 2S,3S,4S). Subsequently, (±)-trans-2,3,4-trimethyl-2-pentenedioic acid was resolved with cinchonidine to give 8a and 8b, whose stereochemistry was assigned respectively as S- and R-configuration by correlation to the known (R)-(−)-2-phenylpropanoic acid. Methylation of 8a followed by cis-hydroxylation and hydrolyses afforded γ-lactone acids, 5a (2R,3S,4S) and 6b (2S,3R,4S). Similarly, th...
11 citations
TL;DR: Bisquaternary dimers of strychnine and brucine were synthesized and their allosteric effect on muscarinic acetylcholine M(2) receptors was examined, which indicated ternary complex formation.
11 citations
TL;DR: Racemic threo-9,10,dihydroxypalmitic acid was resolved by means of the brucine salts into the optically active forms Levorotatory threeso-11,12,dhydroxyeicosanoic acid as discussed by the authors.
Abstract: Racemic threo-9,10-dihydroxypalmitic acid was resolved by means of the brucine salts into the optically active forms Levorotatory threo-11,12-dihydroxyeicosanoic acid was obtained from the corresp
11 citations
TL;DR: From the fruits of Strychnos lucida R.Br, were isolated loganin (1.1 per cent.) which appears to be confined to the pulp, strychnine (0.3 per cent.), and an unresolved glassy alkaloidal mixture as discussed by the authors.
Abstract: From the fruits of Strychnos lucida R.Br, were isolated loganin (1.1 per cent.) which appears to be confined to the pulp, strychnine (0.1 per cent.), brucine (1.3 per cent.), and an unresolved glassy alkaloidal mixture (0.5 per cent.). " Lucidine-S " could not be separated. The leaves of 8. psilosperma F. Muell. contain about 1.1 per cent. total alkaloid from which two new alkaloids, strychnospermine and spermostrychnine, were isolated. Structural formulae for these are suggested on biogenetic grounds. The triterpene alcohol, germanicol, was also isolated from S. psilosperma leaves.
11 citations