5625. Lycoramine

Nomenclature

CAS number: 21133-52-8
1,2-Dihydrogalanthamine; 3,4-dihydrogalanthamine.
C17H23NO3; mol wt 289.37.
C 70.56%, H 8.01%, N 4.84%, O 16.59%.

Description and references

One of the minor alkaloids of Lycoris radiata Herb., Amaryllidaceae: Kondo, Ishiwata, Ber. 70B, 2427 (1937). From Narcissus spp.: Boit et al., ibid. 90, 725 2197 (1957). Tentative structure: Kobayashi, Uyeo, Chem. Ind. (London) 1956, 177. Structure elucidation: William, Rogers, Proc. Chem. Soc. London 1964, 357. Synthesis of the naturally occurring (-)-form: Barton, Kirby, J. Chem. Soc. 1962, 806; of the (±)-form: N. Hazama et al., J. Chem. Soc. C 1968, 2947; Y. Misaka et al., ibid. 2954; A. G. Schultz et al., J. Am. Chem. Soc. 99, 8065 (1977); S. F. Martin, P. J. Garrison, J. Org. Chem. 46, 3567 (1981); 47, 1513 (1982).

Chemical structure

Properties

Plates from acetone, mp 121°. [α]D27 -98° (alcohol). Freely sol in water; sol in alc, acetone. Its salts hydrolyze easily.