Title: Sporidesmins
Literature References: Toxic fungal mixture from Pithomyces chartarum Ellis (Sporidesmium bakeri Sydow), composed of sporidesmins A-H and J, as causative agent of "facial eczema" in sheep. First isoln of A (major metabolite): R. L. M. Synge, E. P. White, Chem. Ind. (London) 1959, 1546. Isoln of A and B: J. W. Ronaldson et al., J. Chem. Soc. C 1963, 3172. Structure of A: J. Fridrichsons, A. M. Mathieson, Tetrahedron Lett. 1962, 1265. Abs config of A: A. F. Beecham et al., ibid. 1966, 3131. Isoln and structure of D and F: W. D. Jamieson et al., J. Chem. Soc. C 1969, 1564; of E: R. Rahman et al., ibid. 1665; of G: E. Francis et al., J. Chem. Soc. Perkin Trans. 1 1972, 470; of H and J: R. Rahman et al., ibid. 1978, 1476. Total synthesis of A: Y. Kishi et al., J. Am. Chem. Soc. 95, 6493 (1973).
Derivative Type: Sporidesmin A
CAS Registry Number: 1456-55-9
CAS Name: (3a,5aa,10ba,11b,11aa)-9-Chloro-2,3,5a,6,10b,11-hexahydro-10b,11-dihydroxy-7,8-dimethoxy-2,3,6-trimethyl-3,11a-epidithio-11aH-pyrazino[1¢,2¢:1,5]pyrrolo[2,3-b]indole-1,4-dione
Additional Names: sporidesmin
Molecular Formula: C18H20ClN3O6S2
Molecular Weight: 473.95
Percent Composition: C 45.62%, H 4.25%, Cl 7.48%, N 8.87%, O 20.25%, S 13.53%
Properties: Colorless needles with a faint green sheen, from aq methanol, mp 179° (dependent on rate of heating). [a]D20 -45° (c = 0.98 in methanol). uv max: 219, 253, 305 nm (E1%1cm 700, 220, 40). Very slightly sol in water, light petroleum, CCl4. Readily sol in most organic solvents.
Melting point: mp 179° (dependent on rate of heating)
Optical Rotation: [a]D20 -45° (c = 0.98 in methanol)
Absorption maximum: uv max: 219, 253, 305 nm (E1%1cm 700, 220, 40)
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