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The constitution of vincamine

J. Mokrý, I. Kompiš, J. Suchy, P. Šefčovič, and Z. Votický

Slovak Academy of Sciences, Bratislava


Abstract: Vincamine C21H26N2O3 (I) m. 234-6.5°, the main alkaloid in Vinca minor is changed by sapon. into vincaminic acid C20H24N2O2 (1I), m. 256-8°, which on treatment with CH2N2 is reconverted to I. On esterification with MeOH satd. with HCl, the ester is dehydrated to apovincamine C21H24N2O2, m. 160-2°, which by dehydrogenation gives 2 carbomethoxy epimers: epideoxyvincamine C21H26N2O2, m. 123-4°, and deoxyvincamine C21H26N2O2, m. 159-60°. By dehydrogenation of I with Se N(a) substituted β-carbolines are formed: vincyrine C19H22N2, m. 107-9° and isovincyrine C19H22N2, b0.01 120°. In the acid portions of CrO3-oxidn. of I, acetic and propionic acids were bound. On the basis of analytical detns., ultraviolet and infrared spectra, and biogenetic data, the structure of I was proposed as 19,20-dihydro-16(e)-carbomethoxy-17(a)-hydroxynorma-vacurine.

Full paper in Portable Document Format: 161-2a140.pdf (in Slovak)


Chemical Papers 16 (1-2) 140–150 (1962)

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