193. Ajaconine

Nomenclature

CAS number: 545-61-9
C22H33NO3; mol wt 359.50.
C 73.50%, H 9.25%, N 3.90%, O 13.35%.

Description and references

From seeds of larkspur, Delphinium ajacis L., Ranunculaceae: Keller, Volker, Arch. Pharm. 251, 207 (1913); Goodson, J. Chem. Soc. 1945, 245. Structure: Dvornik, Edwards, Tetrahedron 14, 54 (1961); Nabors et al., Tetrahedron Lett. 1969, 2445. Stereochemistry: Solo, Pelletier, Chem. Ind. (London) 1960, 1108; Whalley, Tetrahedron 18, 43 (1962). Synthetic studies: Nabors et al., ibid. 27, 2385 (1971). Rearrangement: S. W. Pelletier, N. V. Mody, J. Am. Chem. Soc. 101, 492 (1979).

Chemical structure

Properties

Prisms from dil alcohol, mp 172°. [α]D18 119° (c = 2 in anhydr alcohol).

Derivative

Sulfate heptahydrate.

Properties

Hexagonal plates from dil acetone, mp 113°. [α]D20 +5.5° (c = 2).