Enantioselective synthesis of functionalized tropanes by rhodium(II) carboxylate-catalyzed decomposition of vinyldiazomethanes in the presence of pyrroles

Journal of Organic Chemistry

Volumn 62, Issue 4, 1997, Pages 1095-1105

  Davies, Huw M L ^a   Matasi, Julius J ^a   Mark Hodges, L ^a   Huby, Nicholas J S ^b   Thornley, Craig ^b   Kong, Norman ^a   Houser, Jeffrey H ^a  

^a UNIVERSITY AT BUFFALO   (United States)

^b WAKE FOREST UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANHYDROECGONINE METHYL ESTER; FERRUGININE; TROPANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031003069     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961920w     Document Type: Article

References (55)

1. For a general review, see: (a) Lounasmaa, M.; Tamminen, T. Alkaloids 1993, 44, 1. (b) Lounasmaa, M. Alkaloids 1988, 33, 1.
2. For a general review, see: (a) Lounasmaa, M.; Tamminen, T. Alkaloids 1993, 44, 1. (b) Lounasmaa, M. Alkaloids 1988, 33, 1.
3. (a) Davies, H. M. L.; Saikali, E.; Huby, N. J. S.; Gilliatt, V. J.; Matasi, J. J.; Sexton, T.; Childers, S. R. J. Med. Chem. 1994, 37, 1262.
4. (b) Davies, H. M. L.; Kuhn, L. A.; Thornley, C.; Matasi, J. J.; Sexton, T.; Childers, S. R. J. Med. Chem. 1996, 39, 2554.
5. (c) Carroll, F. I.; Lewin, A. H.; Boja, J. W.; Kuhar, M. J. J. Med. Chem. 1992, 35, 969.
6. (d) Carroll, F. I.; Kotian, P.; Dehghani, A.; Gray, J. L.; Kuzemko, M. A.; Parham, K. A.; Abraham, P.; Lewin, A. H.; Boja, J. W.; Kuhar, M. J. J. Med. Chem. 1995, 38, 379.
7. (e) Kozikowski, A. P.; Roberti, M.; Johnson, K. M.; Bergmann, J. S.; Ball, R. G. Biorg. Med. Chem. Lett. 1993, 3, 1327.
8. (f) Kozikowski, A. P.; Roberti, M.; Xiang, L.; Bergmann, J. S.; Callahan, P. M.; Cunningham, K. A.; Johnson, K. M. J. Med. Chem. 1992, 35, 4764.
9. (g) Kelkar, S. V.; Izenwasser, S.; Katz, J. L.; Klein, C. L.; Zhu, N.; Trudell, M. L. J. Med. Chem. 1994, 37, 3875.
10. (h) Meltzer, P. C.; Liang, A. Y.; Brownell, A.-L.; Elmaleh, D. R.; Madras, B. K. J. Med. Chem. 1993, 36, 855.
11. (a) Willstatter, R. Ber. 1896, 29, 936.
12. (b) Willstatter, R. Justus Liebigs Ann. Chem. 1903, 326, 23.
13. (c) Robinson, R. J. Chem. Soc. 1917, 111, 762.
14. (d) Hayakawa, Y.; Baba, Y.; Makino, S.; Noyori, R. J. Am. Chem. Soc. 1978, 100, 1786.
15. (e) Tufariello, J. J.; Mullen, G. B.; Tegeler, J. J.; Trybulski, E. J.; Wong, S. C.; Asrof Ali, S. J. Am. Chem. Soc. 1979, 101, 2435.
16. (f) Iida, H.; Watanabe, Y.; Kibayashi, C. J. Org. Chem. 1985, 50, 1818.
17. (g) Petersen, J. S.; Toteberg-Kaulen, S.; Rapoport, H. J. Org. Chem. 1984, 49, 2948.
18. (h) Rumbo, A.; Mourino, A.; Castedo, L.; Mascarenas, J. L. J. Org. Chem. 1996, 61, 6114.
19. Dennis, N.; Katritzky, A. R.; Takeuchi, Y. Angew. Chem., Int. Ed. Engl. 1976, 15, 1.
20. (j) Rumbo, A.; Mourino, A.; Castedo, L.; Mascarenas, J. L. J. Org. Chem. 1996, 61, 6114.
21. (a) Hernandez, A. S.; Thaler, A.; Castells, J.; Rapoport, H. J. Org. Chem. 1996, 67, 314.
22. (b) Majewski, M.; Lazny, R. J. Org. Chem. 1995, 60, 5825.
23. (c) Rigby, J. H.; Pigge, F. C. J. Org. Chem. 1995, 60, 7392.
24. Campbell, H. F.; Edwards, O. E.; Kolt, R. Can. J. Chem. 1977, 55, 1372.
25. For preliminary accounts of portions of this work, see: (a) Davies, H. M. L.; Huby, N. J. S. Tetrahedron Lett. 1992, 33, 6935. (b) Davies, H. M. L.; Matasi, J. J.; Thornley, C. Tetrahedron Lett. 1995, 36, 7205.
26. For preliminary accounts of portions of this work, see: (a) Davies, H. M. L.; Huby, N. J. S. Tetrahedron Lett. 1992, 33, 6935. (b) Davies, H. M. L.; Matasi, J. J.; Thornley, C. Tetrahedron Lett. 1995, 36, 7205.
27. Davies, H. M. L.; Saikali, E.; Young, W. B. J. Org. Chem. 1991, 56, 5696.
28. (a) Davies, H. M. L.; Hutcheson, D. K. Tetrahedron Lett. 1993, 34, 7243.
29. (b) Davies, H. M. L.; Peng, Z.; Houser, J. H. Tetrahedron Lett. 1994, 35, 8939.
30. Davies, H. M. L.; Bruzinski, P. R.; Lake, D. H.; Kong, N.; Fall, M. J. J. Am. Chem. Soc. 1996, 118, 6897.
31. (a) Davies, H. M. L.; Huby, N. J. S.; Cantrell, W. R., Jr.; Olive, J. L. J. Am. Chem. Soc. 1993, 115, 9468.
32. (b) Davies, H. M. L.; Ahmed, G.; Churchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774.
33. Davies, H. M. L.; Matasi, J. J.; Ahmed, G. J. Org. Chem. 1996, 61, 2305.
34. Davies, H. M. L.; Cantrell, W. R., Jr.; Romines, K. R.; Baum, J. S. Org. Synth. 1991, 70, 93.
35. (a) Hoye, T. R.; Renner, M. K. J. Org. Chem. 1996, 61, 2056 and references therein.
36. (b) Hoye, T. R.; Renner, M. K. J. Org. Chem., in press.
37. (c) Rauk, A.; Tavares, D. F.; Khan, M. A.; Borkent, A. J.; Olson, J. F. Can. J. Chem. 1983, 61, 2572.
38. Due to the differences in the priority assigned to a dialkylamino group versus a chloro group, the R-acid chloride produces the S-Mosher amide.
39. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.
40. The opposite rotamer is observed exclusively for the Mosher amides of norcocaine described in ref 12b, presumably due to the presence of β-substituents at C2 and C3.
41. The major rotamer observed with one Mosher amide derived from one enantiomer of tropane is enantiomeric with the major rotamer derived from the opposite enantiomer of tropane with the opposite Mosher amide. Since these two compounds have identical NMR spectra, mixtures of Mosher amides can striaghtforwardly be assigned.
42. (a) Porrino, L. J.; Migliarese, K.; Davies, H. M. L.; Saikali, E.; Childers, S. R. Life Sci. 1994, 54, 511-517.
43. (b) Hemby, S. E.; Co, C.; Reboussin, D.; Davies, H. M. L.; Dworkin, S. I.; Smith, J. E. J. Pharmacol. Exp. Ther. 1995, 272, 1176-1186.
44. (c) Porrino, L. J.; Davies, H. M. L.; Childers, S. R. J. Pharmacol. Exp. Ther. 1995, 272, 901.
45. Bray, B. L.; Mathies, P. H.; Naef, R.; Solas, D. R.; Tidwell, T. T.; Artis, D. R.; Muchowski, J. M. J. Org. Chem. 1990, 55, 6317 and references therein.
46. Pirrung, M. C.; Zhang, J.; Lackey, K.; Sternbach, D. D.; Brown, F. J. Org. Chem. 1995, 60, 2112.
47. Acheson, R. M.; Vernon, J. M. J. Chem. Soc. 1961, 457.
48. Reddy, G. S. Chem. Ind. 1965, 1426.
49. Prinzbach, H.; Kaupp, G.; Fuchs, R.; Joyeux, M.; Kitzing, R.; Markert, J. Chem Ber. 1973, 106, 3824.
50. Mikhaleva, A. I.; Trofimov, B. A.; Vasil'ev, A. N.; Komarova, G. A.; Skorobogatova, V. I. Khim. Geterotsikl. Soedin. 1983, 920.
51. Chen, W.; Cava, W. P. Tetrahedron Lett. 1987, 28, 6025.
52. Cornforth, J. W.; Firth, M. E. J. Chem. Soc. 1958, 1091.
53. While the intermediate alcohol is not thermally stable, care must be taken to remove all of the ethanol before the elimination step. Typically, the crude oil was pumped under high vacuum (∼0.5 torr) for at least 30 min before the next step.
54. Note that at lower pH, the BOC protecting group will be removed.
55. Bick, I. R. C.; Gillard, J. W.; Leow, H. M. Aust. J. Chem. 1979, 32, 2537.