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Synthesis of some derivatives of alkaloids. III

I. Ježo and A. Rybár

Slovak Academy of Sciences, Bratislava

 

Abstract: Two methods for prepn. of tetrahydroberberine (I) are described. (1) By treatment of homoprotocatechuic acid dibenzyl ether with homopiperonylamine; N-(3,4-methylenedioxyphenethyl) - 3,4 - dibenzyloxyphenylacetamide is formed and dehydrated to 1-(3,4-dibenzyloxybenzyl)-6,7-methylenedioxy-3,4-dihydroisoquinoline. This is catalytically hydrogenated to 1-(3,4-dihydroxybenzyl)norhydrohydrastinine and finely, after condensation with CH2O and methylation, I is formed. (2) In the 2nd method the reaction with dibenzyl ether is omitted.

Full paper in Portable Document Format: 84a201.pdf (in Slovak)

 

Chemical Papers 8 (4) 201–206 (1954)

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