VINCAMINE (Minorine, Vincamarine)

Description

A further alkaloid isolated from Vinca minor, the base yields colourless crystals from Me2CO or MeOH and has [α]²³_D - 5° (CHCl3) or + 41 ° (pyridine). It contains a non-phenolic hydroxyl group and yields the hydrochloride, m.p. 202-212°C and the picrate, m.p. 228-9°C. The above structure has been confirmed by the total synthesis of the base.

References

Schlittler, Furlenmeier., Helv. Chim. Acta, 36, 2017 (1953) Pailer, Belohlav.,Monatsh., 85, 1055 (1954) King, Gilks, Partridge., J. Chem. Soc., 4206 (1955) Cekan, Trojanek, Zabolotnaja., Tetrahedron Lett., No. 18, 11 (1959) Trojanek et al., Chem. & Ind., 790 (1961) Trojanek et al., Tetrahedron Lett., 702 (1961) Synthesis: Kuehna., J. A mer. Chem. Soc., 86, 2946 (1964) ThaI et al., Compt. Rend., 275C, 1295 (1972) Absolute configuration: Trojanek, Koblicova, Blaha., Collect. Czech. Chem. Commun., 33, 393 (1968)