316. Alstonine

Nomenclature

CAS number: 642-18-2
3,4,5,6,16,17-Hexadehydro-16-(methoxycarbonyl)-19α-methyl-20α-oxayohimbanium.
C21H20N2O3; mol wt 348.40.
C 72.40%, H 5.79%, N 8.04%, O 13.78%.

Description and references

From Alstonia constricta F. Mull., Rauwolfia vomitoria Afzel., Rauwolfia obscura K. Schum., Vinca rosea L., and other Apocynaceae: Sharp, J. Chem. Soc. 1934, 287; Schlittler et al., Helv. Chim. Acta 35, 271 (1952); Pillay, Kumari, J. Sci. Ind. Res. 20B, 458 (1961); C.A. 56, 7425b (1962). Structure: Bader, Helv. Chim. Acta 36, 215 (1953). Stereoisomer of serpentine (alkaloid), q.v. Stereochemistry: Wenkert, Roychaudhuri, J. Am. Chem. Soc. 79, 1519 (1957); 80, 1613 (1958); Shamma, Richey, ibid. 85, 2507 (1963). Biosynthesis: Woodward, Angew. Chem. 68, 13 (1956).

Chemical structure

Properties

Fine, yellow needles from acetone, dec above 300° (brown at 200°, black at 260°). uv max (methanol): 252, 289, 309, 336, 369 nm (log ε 4.54, 4.08, 4.36, 3.39, 3.60). Quickly decomposes on standing in organic solvents, yielding red solns with blue fluorescence.

Derivative

Hydrochloride.
C21H20N2O3.HCl; mol wt 384.86.
C 65.54%, H 5.50%, N 7.28%, O 12.47%, Cl 9.21%.

Properties

Yellow plates from abs alcohol, dec 286°. [α]D +132° (c = 1.06). Sol in water.