Alkaloids phenylethylamine

L-tyrosine Phenylethylamino alkaloids Phenylethylamine Adrenaline Anhalamine Dopamine Noradrealine Tyramine... 

By the method referred to under the benzyl/soquinoline alkaloids (p. 193) Leithe has shown that the configuration of the I- and d-canadines by reference to Z( —)-a-phenylethylamine is l(—) and d(-j-) respectively. 

Nitroalkenes prepared from aromatic aldehydes are especially useful for natural product synthesis. For example, the products are directly converted into ketones via the Nef reaction (Section 6.1) or indoles (Section 10.2) via the reduction to phenylethylamines (Section 6.3.2). The application of these transformations are discussed later here, some examples are presented to emphasize their utility. Schemes 3.3 and 3.4 present a synthesis of 5,6-dihydroxyindole66 and asperidophytine indole alkaloid,67 respectively. 

On the other hand, adults of E. varivestis turned out to be the most versatile alkaloid producer of all ladybird species so far examined. Indeed, not less than 12 alkaloids have been isolated from this beetle, including euphococcinine (32), a complex mixture of simple piperidines (33-36), 2-phenylethylamine (37) and long chain pyrrolidines (38-41) (Fig. 7) [43-45]. The syntheses of optically pure (2S,12 R)-2-(12 -aminotridecyl)-pyrrolidine (38) and (2S,12 R)-l-(2"-hydroxy-... 

Bentley, K. W. 2000. (3-Phenylethylamines and the isoquinoline alkaloids. Nature Product Reports, 17 247-268. 

In toluene with 4 equiv methanol and a catalytic amount of the alkaloid. b ee values are determined by conversion of the monoesters to the (R)-l-(l-naphthalenyl)ethylamides (entries 1-14) and analysis by HPLC, by salt formation with (R)-l-phenylethylamine (entries 15-20) or by H-NMR spectroscopy in the presence of Eu(hfc)3. Absolute configurations are determined by chemical correlation or by X-ray analysis of the Mosher ester of the lactone alcohol (entry 21). With 20 equiv of methanol. d With 4 equiv of methanol. With 10 equiv of methanol. f With 3 equiv of methanol. 

Isoquinoline synthesis Bischler-Napieralski synthesis is used to synthesize isoquinolines. (3-phenylethylamine is acylated, and then cyclodehy-drated using phosphoryl chloride, phosphorus pentoxide or other Lewis acids to yield dihydroisoquinoline, which can be aromatized by dehydrogenation with palladium, for example in the synthesis of papaverine, a pharmacologically active isoquinoline alkaloid. 

Several alkaloids of the phenylethylamine, morphine and Ipecacuanha classes can be detected directly with DNS-C1 [121-124]. This reagent reacts with the primary and secondary amino groups or phenolic hydroxyl groups of the alkaloids to form highly fluorescent derivatives, nanogram amounts of which may be detected after chromatographic separation. 

Zhang H, Kamano Y, Kizu H, Itokawa H, Pettit GR, Herald CL (1994) Convolutamines A-E, Novel P-Phenylethylamine Alkaloids from Marine Bryozoan Amathia convoluta. Chem Lett 2271... 

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