(5α,12R,19α)-2,3-Didehydro-6α,7α-epoxyaspidospermidine-3-carboxylic acid methyl ester Chemical Properties

Melting point:

190-3°C (dec.).

alpha 

D27 -432° (chloroform)

pka

pKa in 66% DMF: 4.2(at 25℃)

(5α,12R,19α)-2,3-Didehydro-6α,7α-epoxyaspidospermidine-3-carboxylic acid methyl ester Usage And Synthesis

Description

One of the numerous alkaloids which have been isolated from Vinca rosea L. (Syn. Catharanthus roseus G. Don.), this base yields colourless crystals from MeOH and is strongly laevorotatory with [α]_D - 528° (CHCl3) or [α]²⁷_D - 432° (CHCI3). The ultraviolet spectrum of the alkaloid in EtOH shows three absorption maxima at 226, 297 and 327 ffi/.l. The suggested structure contains one methoxycarbonyl group, an imino group, a bridge ethyl group and an epoxy ring. The second nitrogen atom is tertiary.

Definition

ChEBI: Lochnericine is an Aspidosperma alkaloid with molecular formula C21H24N2O3 found in the roots of Madagascar periwinkle (Catharanthus roseus, formerly known as Vinca rosea). It has a role as a plant metabolite. It is a monoterpenoid indole alkaloid, an organic heterohexacyclic compound, a methyl ester, an epoxide and an Aspidosperma alkaloid. It is a conjugate base of a lochnericine(1+).

References

Nair, Pillay., Tetrahedron, 6,89 (1959)
Gorman et at., J. Amer. Pharm. Assoc., Sci. Ed., 48, 256 (1959)
Moza, Trojanck., Chem. Ind., 1425 (1962)
Mozaetat., Tetrahedron Lett., 2561 (1964)