3294. Dioscorine

Nomenclature

CAS number: 3329-91-7
[1R-(1α,4α,5α)]-2,4′-Dimethylspiro[2-azabicyclo[2.2.2]octane-5,2′-[2H]pyran]-6′(3′H)-one.
C13H19NO2; mol wt 221.30.
C 70.56%, H 8.65%, N 6.33%, O 14.46%.

Description and references

Found in the tubers of Dioscorea hirsuta Blume and D. hispida Dennst., Dioscoreaceae: H. W. Schutte, Chem. Zentralbl. 68, II, 130 (1897); M. K. Gorter, Rec. Trav. Chim. 30, 161 (1911); A. R. Pinder, Nature 168, 1090 (1951); idem, J. Chem. Soc. 1952, 2236. Structure: W. A. M. Davies et al., Chem. Ind. (London) 1961, 1410; eidem, Tetrahedron 18, 405 (1962); Morris, A. R. Pinder, J. Chem. Soc. 1963, 1841. Synthesis: Page, A. R. Pinder, ibid. 1964, 4811. Absolute configuration: A. F. Beecham et al., Tetrahedron Lett. 1969, 3745. Biosynthetic studies: E. Leete, A. R. Pinder, Chem. Commun. 1971, 1499; E. Leete, J. Am. Chem. Soc. 99, 648 (1977). Pharmacology: A. R. Pinder, J. Chem. Soc. 1953, 1826. Evaluation of toxic components: J. Webster et al., J. Agric. Food Chem. 32, 1087 (1984).

Chemical structure

Properties

Greenish-yellow prisms from ether, mp 54-55°. [α]D18 -35.0° (c = 3.4 in chloroform). uv max (methanol): 215 nm (ε 10160). Distills unchanged in vacuo. Sol in water, alcohol, acetone, chloroform; slightly sol in ether, benzene, petr ether.

Derivative

Hydrochloride.
C13H19NO2.HCl; mol wt 257.76.
C 60.58%, H 7.82%, N 5.43%, O 12.41%, Cl 13.75%.

Properties

Needles from alcohol + ether, dec 210-211°.