ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

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)