Description and references

The aglycon of digitoxin, thevetin, cerberin, echujin, evomonosid. Prepn by refluxing digitoxin in a mixture of water + alcohol + HCl: Cloetta, Arch. Exp. Pathol. Pharmakol. 88, 113 (1920); Stoll, Kreiss, Helv. Chim. Acta 17, 592 (1934). Structure: Jacobs, Hoffmann, J. Biol. Chem. 67, 333 (1926); Jacobs, Gustus, ibid. 78, 573; 79, 533 (1928); 82, 402 (1929); Jacobs, Elderfield, ibid. 108, 497 (1935); Elderfield, Chem. Rev. 17, 187 (1935). Stereochemistry: Meyer, Helv. Chim. Acta 30, 1976 (1947). Synthesis: Danieli et al., Tetrahedron 22, 3189 (1966); W. Fritsch et al., Ann. 1974, 621; S. F. Donovan et al., Tetrahedron Lett. 1979, 3287; R. Marinibettolo et al., Can. J. Chem. 59, 1403 (1981); T. Milkova et al., Tetrahedron Lett. 23, 413 (1982). Biosynthesis from neriifolin, q.v.: A. Cruz et al., J. Org. Chem. 42, 3580 (1977).

Properties

Derivative