Six new indole alkaloids from Gelsemium sempervirens Ait. f.

Tetrahedron Letters

Volumn 46, Issue 35, 2005, Pages 5857-5861

  Kogure, Noriyuki ^a   Nishiya, Chika ^a   Kitajima, Mariko ^a   Takayama, Hiromitsu ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

Gelsemium; Indole alkaloid; Isomerization; NMR; Solvent effect; Structure elucidation; Total synthesis

Indexed keywords

16 EPIVOACARPINE; AMINOKETONE; GELSEMPERVINE A; GELSEMPERVINE B; GELSEMPERVINE C; GELSEMPERVINE D; INDOLE ALKALOID; SEPERVILAM; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; GELSEMIUM; SPECTROSCOPY;

GELSEMIUM; GELSEMIUM SEMPERVIRENS;

EID: 23044479998     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.06.136     Document Type: Article

References (18)

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10. -1): 3451, 3342, 2951, 1732, 1639. CD (c = 0.262 mM, MeOH, 23°C) Δε (λ nm): 0 (396), +1.91 (321), 0 (299), -1.51 (282), 0 (265), +1.12 (257), 0 (243), -10.32 (224), 0 (210), +3.55 (203).
11. D. Ponglux, S. Wongseripipatana, S. Subhadhirasakul, H. Takayama, M. Yokota, K. Ogata, C. Phisalaphong, N. Aimi, and S. Sakai Tetrahedron 44 1988 5075 5094
12. M. Gorman, and J. Sweeny Tetrahedron Lett. 5 1964 3105 3111
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14. S. Sakai, E. Yamanaka, and L. Dolby Yakugaku Zasshi 97 1977 309 319
15. -1): 3313, 2925, 1742, 1640. CD (c = 0.210 mM, MeOH, 23°C) Δε (λ nm): 0 (396), +2.29 (318), 0 (302), -1.64 (286), 0 (264), +1.24 (252), 0 (246), -8.38 (223), 0 (205).
16. 3OD. These correlations enabled us to assign the chemical shift of C-3 in 4, and the HMBC connectivities supported the transannular form in the protic solvent.
17. -1): 3451, 3316, 2928, 1737, 1641. CD (c = 0.224 mM, MeOH, 23°C) Δε (λ nm): 0 (392), +1.46 (318), 0 (301), -1.36 (282), 0 (265), +1.10 (251), 0 (244), -6.99 (224), 0 (214), +3.15 (204).
18. -1): 3330, 2925, 1731. CD (c = 0.272 mM, MeOH, 23°C) Δε (λ nm): 0 (319), +0.79 (271), 0 (244), -13.02 (230), 0 (215), +1.12 (211), +2.16 (206).