Studies on the synthesis of (±)-stenine: A combined intramolecular [4 + 2]-cycloaddition/rearrangement cascade

Journal of Organic Chemistry

Volumn 70, Issue 13, 2005, Pages 5197-5206

  Padwa, Albert ^a   Ginn, John D ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CARBON; CONFORMATIONS; ESTERS; HYDROGENATION; ORGANIC ACIDS; STEREOCHEMISTRY; SULFUR COMPOUNDS; THERMOANALYSIS;

Β-ALKOXY-Γ-DITHIANE LACTAMS; DIMETHYL(METHYLTHIO)SULFONIUM TETRAFLUOROBORATE; INTERMOLECULAR DIELS-ALDER REACTIONS (IMDAF); STEMONA ALKALOID;

SYNTHESIS (CHEMICAL);

ALKALOID; AZEPINE DERIVATIVE; CARBONYL DERIVATIVE; FURAN DERIVATIVE; INDOLE DERIVATIVE; STENINE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CATALYSIS; CHEMICAL BOND; CONFORMATION; CYCLOADDITION; DIELS ALDER REACTION; HYDROGENATION; LACTONIZATION; REACTOR CASCADE; ROOM TEMPERATURE; STEREOCHEMISTRY; SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; STEMONACEAE; STEREOISOMERISM;

ALKALOIDS; COMBINATORIAL CHEMISTRY TECHNIQUES; MOLECULAR STRUCTURE; STEMONACEAE; STEREOISOMERISM;

EID: 20844460780     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050515e     Document Type: Article

References (86)

1. (a) Padwa, A.; Brodney, M. A.; Dimitroff, M. J. Org. Chem. 1998, 63, 5304.
2. (b) Padwa, A.; Dimitroff, M.; Waterson, A. G.; Wu, T. J. Org. Chem. 1998, 63, 3986.
3. (a) Padwa, A.; Brodney, M. A.; Liu, B.; Satake, K.; Wu, T. J. Org. Chem. 1999, 64, 3595.
4. (b) Padwa, A.; Dimitroff, M.; Liu, B. Org. Lett. 2000, 2, 3233.
5. (a) Padwa, A.; Brodney, M. A.; Lynch, S. M. J. Org. Chem. 2001, 66, 1716.
6. (b) Wang, Q.; Padwa, A. Org. Lett. 2004, 6, 2189.
7. (a) Padwa, A.; Dimitroff, M.; Waterson, A. G.; Wu, T. J. Org. Chem. 1997, 62, 4088.
8. (b) Padwa, A.; Brodney, M. A.; Satake, K.; Straub, C. S. J. Org. Chem. 1999, 64, 4617.
9. (c) Lynch, S. M.; Bur, S. K.; Padwa, A. Org. Lett. 2002, 4, 4643.
10. (d) Padwa, A.; Brodney, M. A.; Lynch, S. M.; Rashatasakhon, P.; Wang, Q.; Zhang, H. J. Org. Chem. 2004, 69, 3735.
11. Padwa, A.; Ginn, J. D.; Bur, S. K.; Eidell, C. K.; Lynch, S. M. J. Org. Chem. 2002, 67, 3412.
12. A somewhat related methylthio group migration was reported by Wu and co-workers in their studies of the intramolecular Diels-Alder reaction of a furan containing a tethered allenyl ether dienophile; see: (a) Wu, J.-H.; Shao, W. D.; Ying, F. H. Tetrahedron Lett. 1994, 35, 729.
13. (b) Wu, H.-J.; Ying, F. H.; Shao, W. D. J. Org. Chem. 1995, 60, 6168.
14. (c) Wu, H.-J.; Yen, C. H.; Chuang, C. T. J. Org. Chem. 1998, 63, 5064.
15. For examples of intramolecular Diels-Alder reaction of furans (IMDAF) that contain heteroatoms attached directly to the furan ring; see: (a) Padwa, A.; Kappe, C. O.; Cochran, J. E.; Snyder, J. P. J. Org. Chem. 1997, 62, 2786.
16. (b) Gewald, K. Chem. Ber. 1966, 99, 1002.
17. (c) Boyd, G. V.; Heatherington, K. J. Chem. Soc., Perkin Trans. 1 1973, 2523.
18. (d) Nixon, W. J.; Garland, J. T.; DeWitt-Blanton, C., Jr. Synthesis 1980, 56.
19. (e) Aran, V. J.; Soto, J. L. Synthesis 1982, 513.
20. (f) Semmelhack, M. F.; Park, J. Organometallics 1986, 5, 2550.
21. (g) Chatani, N.; Hanafusa, T. J. Org. Chem. 1987, 52, 4408.
22. (h) Cutler, S. J.; El-Kabbani, F. M.; Keane, C.; Fisher-Shore, S. L.; DeWitt-Blanton, C., Jr. Heterocycles 1990, 31, 651.
23. (i) Vaidya, N. A.; Nixon, W. J.; Fatmi, A. A.; DeWitt-Blanton, C. J. Org. Chem. 1982, 47, 2483.
24. (j) Schlessinger, R. H.; Bergstrom, C. P. Tetrahedron Lett. 1996, 37, 2133.
25. (k) Schlessinger, R. H.; Wu, X.-H.; Pettus, T. R. R. Synlett 1995, 536.
26. (l) Schlessinger, R. H.; Pettus, T. R. R.; Springer, J. P.; Hoogsteen, K. J. Org. Chem. 1994, 59, 3246.
27. (m) Schlessinger, R. H.; Bergstrom, C. P. J. Org. Chem. 1995, 60, 16.
28. (a) Woo, S.; Keay, B. A. Tetrahedron: Asymmetry 1994, 5, 1411.
29. (b) Rogers, C.; Keay, B. A. Tetrahedron Lett. 1991, 32, 6477.
30. (c) Rogers, C.; Keay, B. A. Synlett, 1991, 353.
31. (d) Rogers, C.; Keay, B. A. Can. J. Chem. 1992, 70, 2929.
32. (a) De Clercq, P. J.; Van Royen, L. A. Synth. Commun. 1979, 9, 771.
33. (b) Van Royen, L. A.; Mijngher, R.; De Clercq, P. J. Bull. Soc. Chim. Belg. 1984, 93, 1019.
34. (c) Fischer, K.; Hünig, S. J. Org. Chem. 1987, 52, 564.
35. Bur, S. K.; Lynch, S. M.; Padwa, A. Org. Lett. 2002, 4, 473.
36. 12,13 as implemented by Gaussian 98. We thank Dr. Scott K. Bur for carrying out these calculations.
37. For Becke's three-parameter exchange functional, see: Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
38. For the LYP correlation functional, see: Lee, C.; Yang, W.; Parr, R. Phys. Rev. B 1988, 37, 785.
39. (a) Gotz, M.; Edwards, O. E. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1967; Vol. IX, pp 545-551.
40. (b) Gotz, M.; Edwards, O. E. In The Alkaloids; Weisner, K., Ed.; Academic Press: London, 1973; Vol. IX, pp 143-160.
41. Rende, A. S.; Hernando, J. I. M.; Milbank, J. B. J. Tetrahedron 2002, 58, 61.
42. (a) Pilli, R. A.; Ferreira de Olivera, M. C. Nat. Prod. Rep. 2000, 17, 117.
43. (b) Lin, W.-H.; Ye, Y.; Xu, R.-S. J. Nat. Prod. 1992, 55, 571.
44. (a) Wipf, P.; Rector, S. R.; Takahashi, H. J. Am. Chem. Soc. 2002, 124, 14848.
45. (b) Williams, D. R.; Fromhold, M. G.; Earley, J. D. Org. Lett. 2001, 3, 2721.
46. (c) Martin, S. F.; Barr, K. J.; Smith, D. W.; Bur, S. K. J. Am. Chem. Soc. 1999, 121, 6990.
47. (d) Jacobi, P. A.; Lee, K. J. Am. Chem. Soc. 2000, 122, 4295.
48. (e) Sibi, M. P.; Subramanian, T. Synlett 2004, 1211.
49. (f) Lindsay, K. B.; Pyne, S. G. Synlett 2004, 779.
50. (g) Brüggemann, M.; McDonald, A. I.; Overman, L. E.; Rosen, M. D.; Schwink, L.; Scott, J. P. J. Am. Chem. Soc. 2003, 725, 15284.
51. (h) Rigby, J. H.; Laurent, S.; Cavezza, A. M. J.; Heeg, M. J. J. Org. Chem. 1998, 63, 5587.
52. (i) Hinman, M. M.; Heathcock, C. H. J. Org. Chem. 2001, 66, 7751.
53. (j) Xiang, L.; Kozikowski, A. P. Synlett 1990, 279.
54. (a) Chen, C. Y.; Hart, D. J. J. Org. Chem. 1990, 55, 6236.
55. (b) Chen, C. Y.; Hart, D. J. J. Org. Chem. 1993, 58, 3840.
56. (a) Goldstein, D. M.; Wipf, P.; Kim, Y. J. Am. Chem. Soc. 1995, 117, 11106.
57. (b) Wipf, P.; Kim, Y. Tetrahedron Lett. 1992, 33, 5477.
58. (c) Wipf, P.; Goldstein, D. M. Tetrahedron Lett. 1996, 37, 739.
59. (a) Morimoto, Y.; Iwahashi, M.; Nishida, K.; Hayashi, Y.; Shirahama, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 904.
60. (b) Morimoto, M.; Iwahashi, M. Synlett 1995, 1221.
61. (c) Morimoto, Y.; Iwahashi, M.; Kinoshita, T.; Nishida, K. Chem. Eur. J. 2001, 7, 4107.
62. Golden, J. E.; Aubé, J. Angew. Chem., Int. Ed. 2002, 41, 4316.
63. For a preliminary report of our work, see: Ginn, J. D.; Padwa, A. Org. Lett. 2002, 4, 1515.
64. Padwa, A.; Ginn, J. D.; McClure, M. S. Org. Lett. 1999, 1, 1559.
65. (a) Trost, B. M.; Murayama, E. J. Am. Chem. Soc. 1981, 103, 6529.
66. (b) Trost, B. M.; Sato, T. J. Am. Chem. Soc. 1985, 107, 719. Commercially available from Aldrich Chemical Co.
67. (a) Kice, J. L.; Favstritsky, N. A. J. Am. Chem. Soc. 1969, 91, 1751.
68. (b) Smallcombe, S. H.; Caserio, M. C. J. Am. Chem. Soc. 1971, 93, 5826.
69. (c) Kim, J. K.; Pau, J. K.; Caserio, M. C. J. Org. Chem. 1979, 44, 1544.
70. (a) Braish, T. F.; Saddler, J. C.; Fuchs, P. L. J. Org. Chem. 1988, 53, 3647.
71. (b) Gracia, J.; Casamitjana, N.; Bonjoch, J.; Bosch, J. J. Org. Chem. 1994, 59, 3939.
72. Solladié, G.; Boeffel, D.; Maignan, J. Tetrahedron 1996, 52, 2065.
73. DiMaio, J.; Gibbs, B.; Lefebvre, J.; Konishi, Y.; Munn, D.; Yue, S. J. Med. Chem. 1992, 35, 3331.
74. Gemal, A. L.; Luche, J.-L. J. Am. Chem. Soc. 1981, 103, 5454.
75. Noggle, J. H.; Schirmer, R. E. The Nuclear Overhauser Effect; Academic Press: New York, 1971.
76. Nell, P. G. Synlett 2001, 160.
77. For the preferred addition of hydrogen from one face of a homoallylic alcohol, see: (a) Crabtree, R. H.; Davis, M. W. Organometallics 1983, 2, 681.
78. (b) Stork, G.; Kahne, D. E. J. Am. Chem. Soc. 1983, 105, 1072.
79. Crabtree, R. H.; Felkin, H.; Fillebeen-Khan, T.; Morris, G. E. J. Organomet. Chem. 1979, 168, 183.
80. Keck, G. E.; Yates, J. B. J. Am. Chem. Soc. 1982, 104, 5829.
81. Pappo, R.; Allen, D. S., Jr.; Lemieux, R. U.; Johnson, W. S. J. Org. Chem. 1956, 21, 478.
82. Pedersen, B. S.; Scheibye, S.; Nilsson, N. H.; Lawesson, S.-O. Bull. Soc. Chim. Belg. 1978, 87, 223.
83. Hua, D. H.; Miao, S. W.; Bharathi, S. N. Katsuhira, T.; Bravo, A. A. J. Org. Chem. 1990, 55, 3682.
84. Nakane, M.; Hutchinson, C. J. Org. Chem. 1978, 43, 3922.
85. Knapp, S.; Levorse, A. T. J. Org. Chem. 1988, 53, 4006.
86. Achiwa, K.; Chaloner, P.; Parker, D. J. Organomet. Chem. 1981, 218, 249.