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Synthesis of 4-(1-methyl-2-pyrrolidinyl)isoquinoline under physiological conditions : a model for the biosynthesis of 4-pyrrolidinylisoquinoline alkaloids

✍ Scribed by Edward Leete

Book ID: 104237981
Publisher: Elsevier Science
Year: 1979
Tongue: French
Weight: 125 KB
Volume: 20
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)86640-5

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✦ Synopsis

Tetrahydroisoquinoline-3-carboxylic acid was oxidatively decarboxylated with sodium hypochlorite, affording a dihydroisoquinoline which on condensation with N-methyl-Alpyrrolinium acetate, and subsequent aerial oxidation yielded 4-(1-methyl-2-pyrrolidinyl)isoquinoline.

Arenine (6, R = H) and macrostomine (6, R = Me) are novel isoquinoline alkaloids which have been isolated from Pczpaver arenariwn2 and P. macrosbmun3 respectively. Although no biosynthetic experiments have been carried out on these alkaloids, which contain a pyrrolidine ring at the 4-position of the isoquinoline nucleus, we consider that these alkaloids are formed from norlaudanosoline-3-carboxylic acid (1) which is formed from dopa and 3,4_dihydroxyphenylpyruvic acid. It is suggested that this compound undergoes an oxidative decarboxylation af-(6)

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