677. Annotinine

Nomenclature

CAS number: 559-49-9
C16H21NO3; mol wt 275.34.
C 69.79%, H 7.69%, N 5.09%, O 17.43%.

Description and references

Isoln from Lycopodium annotinum L., Lycopodiaceae: Manske, Marion, Can. J. Res. 21B, 92 (1943). Structure: Przybylska, Marion, Can. J. Chem. 35, 1075 (1957); Wiesner et al., Tetrahedron 4, 87 (1958); Przybylska, Ahmed, Acta Crystallogr. 11, 718 (1958). Stereochemistry: Wiesner et al., Tetrahedron Lett. 1961, 187; Ho, ibid. 1969, 1307. Synthesis: Wiesner et al., Can. J. Chem. 47, 433 (1969). Biogenesis: Leete, Tetrahedron 3, 313 (1958).

Chemical structure

Properties

Brilliant prisms from chloroform + methanol, mp 232°. Sol in chloroform, dil HCl. Sparingly sol in methanol.