Progress toward the syntheses of (+)-GB 13, (+)-himgaline, and himandridine. New insights into intramolecular imine/Enamine aldol cyclizations

Journal of the American Chemical Society

Volumn 134, Issue 19, 2012, Pages 8162-8170

  Evans, David A ^a   Adams, Drew J ^a   Kwan, Eugene E ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COMPUTATIONAL INVESTIGATION; CYCLIZATIONS; DIELS-ALDER; EN-ROUTE; LINEAR PRECURSORS; PROTIC SOLVENTS; SUBSTRATE STRUCTURE; TOTAL SYNTHESIS;

BIOCHEMISTRY; CYCLIZATION; METABOLITES;

NITROGEN COMPOUNDS;

ALKALOID; ENAMINE; GB 13; HIMANDRIDINE; HIMGALINE; IMINE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; DECARBOXYLATION; DIELS ALDER REACTION; DIHYDROXYLATION; ENERGY TRANSFER; MICHAEL ADDITION; MOLECULAR DYNAMICS; OXYGENATION; PHASE TRANSITION; THERMAL ANALYSIS;

ALKALOIDS; BIPHENYL COMPOUNDS; CHEMISTRY TECHNIQUES, SYNTHETIC; CYCLIZATION; HETEROCYCLIC COMPOUNDS; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; IMIDAZOLES; IMINES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; SUBSTRATE SPECIFICITY; TEMPERATURE;

EID: 84862114375     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja3001776     Document Type: Article

References (58)

1. Ritchie, E.; Taylor, W. C. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1967; Vol. 9, Chapter 14, p 529.
2. Collins, D. J.; Culvenor, C. C. J.; Lamberton, J. A.; Loder, J. W.; Price, J. R. Plants for Medicines. A Chemical and Pharmacological Survey of Plants in the Australian Region; CSIRO: Melbourne, 1990; Chapter 1.
3. Pinhey, J. T.; Ritchie, E.; Taylor, W. C. J. Aust. Chem. 1961, 14, 106-126
4. Binns, S. V.; Dunstan, P. J.; Guise, G. B.; Holder, G. M.; Hollis, A. F.; McCredie, R. S.; Pinhey, J. T.; Prager, R. H.; Rasmussen, M.; Ritchie, E.; Taylor, W. C. J. Aust. Chem. 1965, 18, 569-573
5. Mander, L. N.; Ritchie, E.; Taylor, W. C. J. Aust. Chem. 1967, 20, 981-1019
6. Mander, L. N.; Ritchie, E.; Taylor, W. C. J. Aust. Chem. 1967, 20, 1021-1027
7. Guise, G. B.; Mander, L. N.; Prager, R. H.; Rasmussen, M.; Ritchie, E.; Taylor, W. C. J. Aust. Chem. 1967, 20, 1029-1035
8. Mander, L. N.; Prager, R. H.; Rasmussen, M.; Ritchie, E.; Taylor, W. C. J. Aust. Chem. 1967, 20, 1473-1491
9. Mander, L. N.; Prager, R. H.; Rasmussen, M.; Ritchie, E.; Taylor, W. C. J. Aust. Chem. 1967, 20, 1705-1718
10. Thomas, B. Eleusis: J. Psychoact. Plants Compd. 1999, 3, 82-90
11. Kozikowski, A. P.; Fauq, A. H.; Miller, J. H.; McKinney, M. Bioorg. Med. Chem. Lett. 1992, 2, 797-802
12. Malaska, M. J.; Fauq, A. H.; Kozikowski, A. P.; Aagaard, P. J.; McKinney, M. Bioorg. Med. Chem. Lett. 1995, 5, 61-66
13. Clasby, M. C.; Chackalamannil, S.; Czarniecki, M.; Doller, D.; Eagen, K.; Greenlee, W. J.; Lin, Y.; Tsai, H.; Xia, Y.; Ahn, H.-S.; Agans-Fantuzzi, J.; Boykow, G.; Chintala, M.; Foster, C.; Bryant, M.; Lau, J. Bioorg. Med. Chem. Lett. 2006, 16, 1544-1548
14. Chackalamannil, S.; Xia, Y. Expert Opin. Ther. Pat. 2006, 16, 493-505
15. Chackalamannil, S.; Wang, Y.; Greenlee, W. J.; Hu, Z.; Xia, Y.; Ahn, H.-S.; Boykow, G.; Hsieh, Y.; Palomanda, J.; Agans-Fantuzzi, J.; Kurowski, S.; Graziano, M.; Chintala, M. J. Med. Chem. 2008, 51, 3061-3064
16. Hart, D. J.; Wu, W.-L.; Kozikowski, A. P. J. Am. Chem. Soc. 1995, 117, 9369-9370
17. Chackalamannil, S.; Davies, R. J.; Aserom, T.; Doller, D.; Leone, D. J. Am. Chem. Soc. 1996, 118, 9212-9213
18. Takadoi, M.; Katoh, T.; Ishiwata, A.; Terashima, S. Tetrahedron Lett. 1999, 40, 3399-3402
19. Tchabanenko, K.; Adlington, R. M.; Cowley, A. R.; Baldwin, J. E. Org. Lett. 2005, 7, 585-588
20. Tchabanenko, K.; Chesworth, R.; Parker, J. S.; Anand, N. K.; Russell, A. T.; Adlington, R. M.; Baldwin, J. E. Tetrahedron 2005, 61, 11649-11656
21. Chackalamannil, S.; Doller, D.; McQuade, R.; Ruperto, V. Bioorg. Med. Chem. Lett. 2004, 14, 3967-3970
22. Doller, D.; Chackalamannil, S.; Czarniecki, M.; McQuade, R.; Ruperto, V. Bioorg. Med. Chem. Lett. 1999, 9, 901-906
23. Takadoi, M.; Katoh, T.; Ishiwata, A.; Terashima, S. Tetrahedron 2002, 58, 9903-9923
24. Mander, L. N.; McLachlan, M. M. J. Am. Chem. Soc. 2003, 125, 2400-2401
25. McLachlan, M. M. Ph.D. thesis, Research School of Chemistry, Australian National University, 2002.
26. Movassaghi, M.; Hunt, D. K.; Tjandra, M. J. Am. Chem. Soc. 2006, 128, 8126-8127
27. Shah, U.; Chackalamannil, S.; Ganguly, A. K.; Chelliah, M.; Kolutuchi, S.; Beuvich, A.; McPhail, A. J. Am. Chem. Soc. 2006, 128, 12654-12655
28. Larson, K. K.; Sarpong, R. J. Am. Chem. Soc. 2009, 131, 13244-13245
29. Zi, W.; Yu, S.; Ma, D. Angew. Chem., Int. Ed. 2010, 49, 5887-5890
30. Willis, A. C.; O'Connor, P. D.; Taylor, W. C.; Mander, L. N. Aust. J. Chem. 2006, 59, 629-632
31. Movassaghi, M.; Tjandra, M.; Qi, J. J. Am. Chem. Soc. 2009, 131, 9648-9650
32. O'Connor, P. D.; Mander, L. N.; McLachlan, M. M. W. Org. Lett. 2004, 6, 703-706
33. For an initial communication of this work, see: Evans, D. A.; Adams, D. J. J. Am. Chem. Soc. 2007, 129, 1048-1049
34. Claus, R. E.; Schreiber, S. L. Organic Syntheses; Wiley & Sons: New York, 1990; Collect. Vol. 7, pp 168-172.
35. For preparation of 3 and HWE procedure, see: Evans, D. A.; Miller, S. J.; Lectka, T.; von Matt, P. J. Am. Chem. Soc. 1999, 121, 7559-7573
36. Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238-1256
37. Dess, D. B; Martin, J. C. J. Am. Chem. Soc. 1983, 48, 4155-4156
38. Holmquist, C. R.; Roskamp, E. J. J. Org. Chem. 1989, 54, 3258-3260
39. Raban, M.; Noe, E. A.; Yamamoto, G. J. Am. Chem. Soc. 1977, 99, 6527-6731
40. For similar ring systems formed using aldol additions, see: Heathcock, C. H.; von Geldern, T. W. Heterocycles 1987, 25, 75-78
41. Alexakis, A.; Chapdlaine, M. J.; Posner, G. H. Tetrahdron Lett. 1978, 44, 4209-4212
42. Lohray, B. B.; Zimbiniski, R. Tetrahdron Lett. 1990, 50, 7273-7276
43. a 25.8 vs 27.1, DMSO). Bordwell, F. G.; Fried, H. E. J. Org. Chem. 1991, 56, 4218-4223
44. Nicolau, K. C.; Montagnon, T.; Baran, P. S. J. Am. Chem. Soc. 2002, 124, 2245-2258
45. Evans, D. A.; Gage, J. R.; Leighton, J. L.; Kim, A. S. J. Org. Chem. 1992, 57, 1961-1963
46. Hoffmann, R. W. Chem. Rev. 1989, 89, 1841-1860
47. These conditions were used previously to effect nucleophilic displacement of allylic halides. See ref 7c and: Boyd, D. R.; Sharma, N. D.; Kerley, N. A.; McConville, G.; Allen, C. C. R.; Blacker, A. J. ARKIVOC 2003, vii, 32-48
48. Page, M. I.; Jencks, W. P. Proc. Natl. Acad. Sci. U.S.A. 1971, 68, 1678-1683
49. Maple, S. R.; Allerhand, A. J. Am. Chem. Soc. 1987, 109, 6609-6614
50. An analogous intramolecular aldol addition, cyclization of 2,6-heptanedione to 3-hydroxy-3-methylcyclohexanone, is substantially exergonic (Δ G = -2.4 kcal/mol), suggesting that intramolecularity can increase the favorability of an aldol process by 5-6 kcal/mol. Guthrie, J. P.; Guo, J. J. Am. Chem. Soc. 1996, 118, 11472-11487
51. CBS-QB3: Montgomery, J. A., Jr.; Frisch, M. J.; Ochterski, J. W.; Petersson, G. A. J. Chem. Phys. 1999, 110, 2822-2827
52. SMD solvation: Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B. 2009, 113, 6378-6396
53. Song, J.-W.; Tsuneda, T.; Sato, T.; Hirao, K. Org. Lett. 2010, 12, 1440-1443
54. Pieniazek, S. N.; Clemente, F. R.; Houk, K. N. Angew. Chem., Int. Ed. 2008, 47, 7746-7749
55. Wheeler, S. E.; Moran, A.; Pieniazek, S. N.; Houk, K. N. J. Phys. Chem. A 2009, 113, 10376
56. Movassaghi, M.; Chen, B. Angew. Chem., Int. Ed. 2006, 45, 565-568
57. Howells, D. M.; Barker, S. M.; Watson, F. C.; Light, M. E.; Hursthouse, M. B.; Kilburn, J. D. Org. Lett. 2004, 6, 1943
58. Bahmanyar, S.; Houk, K. N. J. Am. Chem. Soc. 2001, 123, 11273-11283