Total synthesis, relay synthesis, and structural confirmation of the C18-norditerpenoid alkaloid neofinaconitine

Journal of the American Chemical Society

Volumn 135, Issue 38, 2013, Pages 14313-14320

  Shi, Yuan ^a,b   Wilmot, Jeremy T ^a,c   Nordstrøm, Lars Ulrik ^a,d   Tan, Derek S ^a   Gin, David Y ^a  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^b ELI LILLY AND COMPANY   (United States)

^c DOW AGROSCIENCES LLC   (United States)

^d ALBERT EINSTEIN COLLEGE OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CONJUGATE ADDITION; DIELS-ALDER CYCLOADDITIONS; DIELS-ALDER REACTION; IDENTICAL STRUCTURES; RADICAL CYCLIZATIONS; STERICALLY DEMANDING; STRUCTURAL CONFIRMATION; X-RAY CRYSTALLOGRAPHIC ANALYSIS;

ALKALOIDS; CYCLOADDITION; ISOMERS; NITROGEN COMPOUNDS; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

METABOLITES;

9 DEOXYLAPPACONITINE; ACONITINE; ACONITINE DERIVATIVE; ALKALOID DERIVATIVE; ALKENE DERIVATIVE; AZEPINONE DIENOPHILE; BROMINE; CARBON; CONDELPHINE; CYCLOPENTADIENE; CYCLOPROPENE; DELPHICRISPULINE; HYDROXYL GROUP; NEOFINACONITINE; TERPENE DERIVATIVE; TERPENOID DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; BIOTRANSFORMATION; CHEMICAL COMPOSITION; CONTROLLED STUDY; CRYSTAL STRUCTURE; CYCLOADDITION; DIASTEREOISOMER; DIELS ALDER REACTION; DRUG SYNTHESIS; MANNICH REACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SUBSTITUTION REACTION; X RAY CRYSTALLOGRAPHY;

ACONITINE; CRYSTALLOGRAPHY, X-RAY; CYCLOADDITION REACTION; DITERPENES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE;

EID: 84884840483     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja4064958     Document Type: Article

References (52)

1. Amiya, T.; Bando, H. Aconitum Alkaloids. In The Alkaloids: Chemistry and Pharmacology; Brossi, A., Ed.; Academic Press: San Diego, 1988; Vol. 34, pp 95-179.
2. 19-Diterpenoid Alkaloids. In The Alkaloids: Chemistry and Biology; Cordell, G. A., Ed.; Elsevier: Amsterdam, 2010; Vol. 69, p 1.
3. 18-Diterpene Alkaloids. In The Alkaloids: Chemistry and Biology; Cordell, G. A., Ed.; Elsevier: Amsterdam, 2009; Vol. 67, p 1.
4. Huang, T. K. Handbook of Composition and Pharmacological Action of Commonly-Used Traditional Chinese Medicine; Yi-Yao Science & Technology Press: Beijing, 1994; pp 923-926, 1367-1372.
5. Wang, F.-P.; Chen, Q.-H.; Liu, X.-Y. Nat. Prod. Rep. 2010, 27, 529-570
6. Schmidt, E.; Schulze, H. Arch. Pharm. 1906, 244, 136-159
7. Schulze, H.; Ulfert, F. Arch. Pharm. 1922, 260, 230-243
8. Wiesner, K.; Götz, M.; Simmons, D. L.; Fowler, L. R.; Bachelor, F. W.; Brown, R. F. C.; Büchi, G. Tetrahedron Lett. 1959, 1 (2) 15-24
9. Wiesner, K.; Bickelhaput, F.; Babin, D. R.; Götz, M. Tetrahedron Lett. 1959, 1 (3) 11-14
10. Ameri, A. Prog. Neurobiol. 1998, 56, 211-235
11. Sadikov, A. Z.; Shakirov, T. T. Khim. Prir. Soedin. 1988, 24, 91-94
12. Synthesis: Wiesner, K.; Tsai, T. Y. R.; Huber, K.; Bolton, S. E.; Vlahov, R. J. Am. Chem. Soc. 1974, 96, 4990-4992
13. Structure determination: Khaimova, M. A.; Palamereva, M. D.; Mollov, N. M.; Krestev, V. P. Tetrahedron 1971, 27, 819-822
14. Tsai, T. Y. R.; Tsai, C. S. J.; Sy, W. W.; Shanbhag, M. N.; Liu, W. C.; Lee, S. F.; Wiesner, K. Heterocycles 1977, 7, 217-226
15. Wiesner, K.; Tsai, T. Y. R.; Nambiar, K. P. Can. J. Chem. 1978, 56, 1451-1454
16. Lee, S. F.; Sathe, G. M.; Wy, W. W.; Ho, P. T.; Wiesner, K. Can. J. Chem. 1976, 54, 1039-1051
17. Wiesner, K. Pure Appl. Chem. 1979, 51, 689-703
18. Wiesner, K. Tetrahedron 1985, 41, 485-497
19. Shishido, K.; Hiroya, K.; Fukumoto, K.; Tetsuji, K. Tetrahedron Lett. 1986, 27, 1167-1170
20. Taber, D. F.; Liang, J.-L.; Chen, B.; Cai, L. J. Org. Chem. 2005, 70, 8739-8742
21. Conrad, R. M.; Du Bois, J. Org. Lett. 2007, 9, 5465-5468
22. Yang, Z.-K.; Chen, Q.-H.; Wang, F.-P. Tetrahedron 2011, 67, 4192-4195
23. Neofinaconitine: Jiang, S.; Hong, S.; Song, B.; Zhu, Y.; Zhou, B. Acta Chim. Sin. 1988, 46, 26-29
24. Delphicrispuline: Ulubelen, A.; Merivli, A. H.; Merivli, F.; Kolak, U.; Ilarslan, R.; Voelter, W. Phytochemistry 1999, 50, 513-516
25. Diels, O.; Alder, K. Liebigs Ann. Chem. 1928, 460, 98-122
26. Wiberg, K. B.; Bartley, W. J. J. Am. Chem. Soc. 1960, 82, 6375-6380
27. Kagi, R. I.; Johnson, B. L. Aust. J. Chem. 1975, 28, 2175-2187
28. McLean, S.; Haynes, P. Tetrahedron 1965, 21, 2329-2342
29. Hudon, J.; Cernak, T. A.; Ashenhurst, J. A.; Gleason, J. L. Angew. Chem., Int. Ed. 2008, 47, 8885-8888
30. Jones, D. W. J. Chem. Soc., Chem. Commun. 1980, 739-740
31. McClinton, M. A.; Sic, V. J. Chem. Soc., Perkin Trans. 1 1992, 1891-1895
32. Wellman, M. A.; Burry, L. C.; Letourneau, J. E.; Bridson, J. N.; Miller, D. O.; Burnell, D. J. J. Org. Chem. 1997, 62, 939-946
33. Al Dulayymi, A. R.; Al Dulayymi, J. R.; Baird, M. S.; Gerrard, M. E.; Koza, G.; Harkins, S. D.; Roberts, E. Tetrahedron 1996, 52, 3409-3424
34. Curran, T. T.; Hay, D. A.; Koegel, C. P.; Evans, J. C. Tetrahedron 1997, 53, 1983-2004
35. Forsyth, C. J.; Clardy, J. J. Am. Chem. Soc. 1990, 112, 3497-3505
36. Wadsworth, W.; Emmons, W. D. J. Am. Chem. Soc. 1961, 83, 1733-1738
37. Levin, J. I.; Turos, E.; Weinreb, S. M. Synth. Commun. 1982, 12, 989-993
38. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815-3818
39. Luke, G. P.; Morris, J. J. Org. Chem. 1995, 60, 3013-3019
40. Hiyamizu, H.; Ooi, H.; Inomoto, Y.; Esumi, T.; Iwabuchi, Y.; Hatakeyama, S. Org. Lett. 2001, 3, 473-475
41. Zhou, G.; Hu, Q.; Corey, E. J. Org. Lett. 2003, 5, 3979-3982
42. Marzorati, M.; Hult, K.; Riva, S.; Danieli, B. Adv. Synth. Catal. 2007, 349, 1963-1968
43. Parikh, J. R.; Doering, W. V. E. J. Am. Chem. Soc. 1967, 89, 5505-5507
44. Grieco, P. A.; Miyashita, M. J. Org. Chem. 1974, 39, 120-122
45. Nicolaou, K. C.; Adsool, V. A.; Hale, C. R. H. Org. Lett. 2010, 12, 1552-1555
46. Renzo, R.; Yuji, N.; Manfred, S. Tetrahedron 1991, 47, 4603-4610
47. Breytenbach, J. C.; Zyl, J. J.; Merwe, P. J.; Rall, G. J. H.; Roux, D. G. J. Chem. Soc., Perkin Trans. 1 1981, 2684-2691
48. Abdelrahman, D.; Benn, M.; Hellyer, R.; Parvez, M.; Edwards, O. E. Can. J. Chem. 2006, 84, 1167-1173
49. Schepartz, A.; Breslow, R. J. Am. Chem. Soc. 1987, 109, 1814-1826
50. Barker, D.; Brimble, M. A.; McLeod, M. D. Tetrahedron 2004, 60, 5953-5963
51. DiBiase, G. J. Org. Chem. 1978, 43, 447-452
52. Hanuman, J. B.; Katz, A. Phytochemistry 1994, 35, 1527-1543