エメチンの合成研究(第2報)Rubremetinium Bromideの全合成

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概要

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• Synthesis of rac-emetine was attempted on the working basis described in the preceding paper, ^<1)> starting from homoveratrylamine, formaldehyde, and ethylmalonic acid. Distinct from the former case, most of the important intermediates were not obtained in a crystalline state, rendering the structure of the ultimate compound ambiguous. When however the penultimate compound, tetradehydroemetinium salt (XII) was submitted to dehydrogenation by means of mercuric acetate, there was obtained rac-rubremetinium bromide (I) in beautifully crystallized state. Structural identity of this salt with the one prepared from natural emetine was established through the direct comparison of their ultrabiolet and infrared spectra. Evidence was thus provided for the correctness of this route for the synthesis of emetine.

• 公益社団法人日本薬学会の論文
• 1955-02-20

著者

• 伴 義雄

  Pharmaceutical Institute Medical Faculty University Of Tokyo

関連論文

• Infrared Spectra of Some Indole and Pyrrole Compounds
• Reaction of 1-Phenethyl-2 (1H)-pyridones with Phosphoryl Chloride. Formation of 1-Phenethyl-2-chloropyridinium Salts.
• The Preparation of 2-(Substituted phenyl) ethanols.
• Reaction of 1-(Phenethyl)-2 (1H)-pyridones with Phosphoryl Chloride. Formation of 1-(Phenethyl)-2-chloropyridinium Salts.
• Preliminary Studies on the Stereochemistry of Emetine. II. Ultraviolet and Infrared Absorption Spectra of 3,4-Dihydroisoquinoline and its Homologs
• Preliminary Studies on the Stereochemistry of Emetine. I. Mercuric Acetate Dehydrogenation of (-)-2'-Acylemetines
• エメチンの合成研究(第2報)Rubremetinium Bromideの全合成
• The Enamine-Immonium Cation System of 9,10-Dimethoxy-1,2,3,4,6,7-hexahydrobenzo [a] quinolizinium Salt

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