Wieland-Gumlich Aldehyde

Title: Wieland-Gumlich Aldehyde
CAS Registry Number: 466-85-3
CAS Name: (17R)-19,20-Didehydro-17,18-epoxycuran-17-ol
Additional Names: 1-deacetyldiaboline; caracurine VII
Molecular Formula: C19H22N2O2
Molecular Weight: 310.39
Percent Composition: C 73.52%, H 7.14%, N 9.03%, O 10.31%
Literature References: Decompn product of isonitrosostrychnine: Wieland, Kaziro, Ann. 506, 60 (1933). Isoln from Strychnos toxifera Benth., and S. subcordata Spruce, Loganiaceae: Asmis et al., Helv. Chim. Acta 37, 1983 (1954); Penna et al., Gazz. Chim. Ital. 87, 1163 (1957). Identity with caracurine VII: Bernauer et al., Helv. Chim. Acta 41, 1405 (1958). Structure: Deyrup et al., ibid. 45, 2266 (1962). Chemistry of the degradation from strychnine, q.v.: Hymon et al., ibid. 52, 1564-1602 (1969). Synthesis: L. Szabo, O. Clauder, Acta Chim. Acad. Sci. Hung. 95, 85 (1977). 13C-NMR study: E. Wenkert et al., J. Org. Chem. 43, 1099 (1978).
Properties: Crystals from acetone + methanol, decomp 213-214°. [a]D22 -133.8° (c = 0.52 in methanol). Sol in methanol, ethanol, chloroform; slightly sol in acetone, ethyl acetate.
Optical Rotation: [a]D22 -133.8° (c = 0.52 in methanol)
Derivative Type: Hydrochloride hemihydrate
Properties: Crystals from ethanol, mp >300°. uv max (water): 240, 290 nm (log e 3.80, 3.40). Sol in water, ethanol, methanol, warm chloroform; slightly sol in acetone, chloroform.
Melting point: mp >300°
Absorption maximum: uv max (water): 240, 290 nm (log e 3.80, 3.40)
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