References of Spiro[9H-benzo[a]fluorene-9,2'(3'H)-furo[3,2-b]pyridin]-11(1H)-one,2,3,3'a,4,4',5',6,6',6a,6b,7,7',7'a,8,11a,11b-hexadecahydro-3-hydroxy-3',6',10,11b-tetramethyl-,(2'R,3S,3'R,3'aS,6'S,6aS,6bS,7'aR,11aS,11bR)-
Title: Jervine
CAS Registry Number: 469-59-0
CAS Name: (3b,23b)-17,23-Epoxy-3-hydroxyveratraman-11-one
Molecular Formula: C27H39NO3
Molecular Weight: 425.60
Percent Composition: C 76.20%, H 9.24%, N 3.29%, O 11.28%
Literature References: Steroidal alkaloid found in
Veratrum grandiflorum (Maxim.) Loes F.,
V. album L.,
V. viride Sol.,
Liliaceae: Saito,
Bull. Chem. Soc. Jpn. 9, 15 (1934),
C.A. 28, 2463 (1934); Poethke,
Arch. Pharm. 275, 357, 571 (1937);
276, 170 (1938);
282, 56 (1944); Seiferle
et al., J. Econ. Entomol. 35, 35 (1942); Jacobs, Craig,
J. Biol. Chem. 160, 555 (1945). Structure: Fried
et al., J. Am. Chem. Soc. 73, 2970 (1951).
Reviews: Wintersteiner in Graff,
Essays in Biochemistry (Wiley, New York, 1956) pp 308-321;
idem, Festschrift Arthur Stoll (Basel, 1957) pp 166-176; L. F. Fieser, M. Fieser,
Steroids (Reinhold, New York, 1959) pp 870-877. Stereochemistry: Sicher, Tichy,
Tetrahedron Lett. no. 12, 6 (1959); Augustine,
Chem. Ind. (London) 196l, 1448; Mitsuhashi, Shimizu,
Tetrahedron 19, 1027 (1963); Bailey
et al., Tetrahedron Lett. 1963, 555; Masamune
et al., ibid. 1965, 489. Revised stereochemistry: Scott
et al., ibid. 1967, 2381; Kupchan, Suffness,
J. Am. Chem. Soc. 90, 2730 (1968); Sprague
et al., Tetrahedron 27, 4857 (1971). Total synthesis: Kutney
et al., Can. J. Chem. 53, 1796 (1975). Comparative toxicity: O. Krayer
et al., J. Pharmacol. Exp. Ther. 82, 167 (1944); K. Tanaka,
ibid. 113, 89 (1955).
Properties: Needles from methanol + water, mp 243.5-244.5° (Saito). [a]D20 -150° (ethanol) (Saito); [a]D20 -167.6° (chloroform) (Poethke). uv max: 250, 360 nm (e 15000, 60). LD50 i.v. in mice: 9.3 mg/kg (Krayer). LD50 s.c. in male mice: 29 mg/kg (Tanaka).
Melting point: mp 243.5-244.5° (Saito)
Optical Rotation: [a]D20 -150° (ethanol) (Saito); [a]D20 -167.6° (chloroform) (Poethke)
Absorption maximum: uv max: 250, 360 nm (e 15000, 60)
Toxicity data: LD50 i.v. in mice: 9.3 mg/kg (Krayer); LD50 s.c. in male mice: 29 mg/kg (Tanaka)
Derivative Type: Diacetyljervine
Molecular Formula: C31H43NO5
Molecular Weight: 509.68
Percent Composition: C 73.05%, H 8.50%, N 2.75%, O 15.70%
Properties: mp 173-175°. [a]D -112°. uv max (ethanol): 250, 360 nm (e 16400, 80).
Melting point: mp 173-175°
Optical Rotation: [a]D -112°
Absorption maximum: uv max (ethanol): 250, 360 nm (e 16400, 80)
Derivative Type: Hydrochloride
Properties: mp 300-302°.
Melting point: mp 300-302°