9988. Vindoline

Nomenclature

CAS number: 2182-14-1
(2β,3β,4β,5α,12β,19α)-4-(Acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methylaspidospermidine-3-carboxylic acid methyl ester.
C25H32N2O6; mol wt 456.53.
C 65.77%, H 7.07%, N 6.14%, O 21.03%.

Description and references

Major alkaloid from the leaves of Vinca rosea Linn. (Catharanthus roseus G. Don.), Apocynaceae; occurs naturally as the ()-form: Gorman et al., J. Am. Pharm. Assoc. 48, 256 (1959); Svoboda et al., ibid. 659; Moza, Trojánek, Collect. Czech. Chem. Commun. 28, 1419 (1963). Structure: Gorman et al., J. Am. Chem. Soc. 84, 1058 (1962); Neuss, Bull. Soc. Chim. Fr. 1963, 1509. Stereochemistry: Moncrief, Lipscomb, J. Am. Chem. Soc. 87, 4963 (1965). Review of chemistry: Neuss et al., Adv. Chemother. 1, 133 (1964). Total synthesis of (±)-vindoline: Ando et al., J. Am. Chem. Soc. 97, 6880 (1975); Y. Ban et al., Tetrahedron Lett. 1978, 151; J. P. Kutney et al., J. Am. Chem. Soc. 100, 4220 (1978). Lacks physiological activity alone but is contained as the pentacyclic moiety in the antineoplastic agents vinblastine and vincristine, q.q.v.

Chemical structure

Properties

Needles from acetone + petr ether, mp 164-165°; prisms, mp 174-175°; [α]D20 18° (chloroform); pKa 5.5 in 66% DMF (Moza, Trojánek). Also reported as crystals, mp 154-155°; [α]D27 +42° (chloroform) (Gorman). uv max (ethanol): 212, 250, 304 nm (log ε 4.49, 3.74, 3.57).

Derivative

Hydrochloride.
C25H32N2O6.HCl; mol wt 492.99.
C 60.91%, H 6.75%, N 5.68%, O 19.47%, Cl 7.19%.

Properties

Crystals from acetone, mp 161-164°.

Derivative

Demethoxyvindoline.

Nomenclature

CAS number: 5231-60-7
Vindorosine; vindolidine.
C24H30N2O5; mol wt 426.51.
C 67.59%, H 7.09%, N 6.57%, O 18.76%.

Description and references

Structure: Moza, Trojánek, Collect. Czech. Chem. Commun. 28, 1427 (1963).

Properties

Needles from benzene + petr ether, mp 167°. [α]D16 31° (chloroform). uv max (methanol): 250, 302 nm (log ε 3.98, 3.52).