5264. Jervine

Nomenclature

CAS number: 469-59-0
(2′R,3S,3′R,3′aS,6′S,6aS,6bS,7′aR,11aS,11bR)-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-tetramethylspiro[9H-benzo[a]fluorene-9,2′(3′H)-furo[3,2-b]pyridin]-11(1H)-one; (3β,23β)-17,23-epoxy-3-hydroxyveratraman-11-one.
C27H39NO3; mol wt 425.60.
C 76.20%, H 9.24%, N 3.29%, O 11.28%.

Description and 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).

Chemical structure

Properties

Needles from methanol + water, mp 243.5-244.5° (Saito). [α]D20 150° (ethanol) (Saito); [α]D20 167.6° (chloroform) (Poethke). uv max: 250, 360 nm (ε 15000, 60). LD50 i.v. in mice: 9.3 mg/kg (Krayer). LD50 s.c. in male mice: 29 mg/kg (Tanaka).

Derivative

Diacetyljervine.

Nomenclature

CAS number: 7622-06-2
C31H43NO5; mol wt 509.68.
C 73.05%, H 8.50%, N 2.75%, O 15.70%.

Properties

mp 173-175°. [α]D 112°. uv max (ethanol): 250, 360 nm (ε 16400, 80).

Derivative

Hydrochloride.

Nomenclature

CAS number: 903508-18-9
C27H39NO3.HCl; mol wt 462.06.
C 70.18%, H 8.73%, N 3.03%, O 10.39%, Cl 7.67%.

Properties

mp 300-302°.