A thio-Diels-Alder route to the azocine ring system. Total synthesis of (±)-otonecine

Journal of the American Chemical Society

Volumn 120, Issue 15, 1998, Pages 3613-3622

  Vedejs, Edwin ^a   Galante, Rocco J ^a   Goekjian, Peter G ^a,b  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b MISSISSIPPI STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLIZIDINE DERIVATIVE;

ARTICLE; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STOICHIOMETRY; SYNTHESIS;

EID: 0032557197     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja973464e     Document Type: Article

References (65)

1. (a) Zhdanovich, E. S.; Men'shikov, G. P. Zh. Obsch. Khim. 1941, 11, 835. Leonard, N. J. Rec. Chem. Prog. 1956, 17, 243. Bürgi, H. B.; Dunitz, J. D. Acc. Chem. Res. 1983, 16, 153.
2. (a) Zhdanovich, E. S.; Men'shikov, G. P. Zh. Obsch. Khim. 1941, 11, 835. Leonard, N. J. Rec. Chem. Prog. 1956, 17, 243. Bürgi, H. B.; Dunitz, J. D. Acc. Chem. Res. 1983, 16, 153.
3. (a) Zhdanovich, E. S.; Men'shikov, G. P. Zh. Obsch. Khim. 1941, 11, 835. Leonard, N. J. Rec. Chem. Prog. 1956, 17, 243. Bürgi, H. B.; Dunitz, J. D. Acc. Chem. Res. 1983, 16, 153.
4. (b) Wunderlich, J. A. Acta Crystallogr. 1961, 23, 846. Culvenor, C. C. J.; O'Donovan, G. M.; Smith, L. W. Aust. J. Chem. 1967, 20, 801. Bernbaum, G. I. J. Am. Chem. Soc. 1974, 96, 6165. Peŕez-Salazar, A.; Cano, F. H.; Fayos, J.; Martinez-Carrera, S.; Garcia-Blanco, S. Acta Crystallogr. 1977, B33, 3525.
5. (b) Wunderlich, J. A. Acta Crystallogr. 1961, 23, 846. Culvenor, C. C. J.; O'Donovan, G. M.; Smith, L. W. Aust. J. Chem. 1967, 20, 801. Bernbaum, G. I. J. Am. Chem. Soc. 1974, 96, 6165. Peŕez-Salazar, A.; Cano, F. H.; Fayos, J.; Martinez-Carrera, S.; Garcia-Blanco, S. Acta Crystallogr. 1977, B33, 3525.
6. (b) Wunderlich, J. A. Acta Crystallogr. 1961, 23, 846. Culvenor, C. C. J.; O'Donovan, G. M.; Smith, L. W. Aust. J. Chem. 1967, 20, 801. Bernbaum, G. I. J. Am. Chem. Soc. 1974, 96, 6165. Peŕez-Salazar, A.; Cano, F. H.; Fayos, J.; Martinez-Carrera, S.; Garcia-Blanco, S. Acta Crystallogr. 1977, B33, 3525.
7. (b) Wunderlich, J. A. Acta Crystallogr. 1961, 23, 846. Culvenor, C. C. J.; O'Donovan, G. M.; Smith, L. W. Aust. J. Chem. 1967, 20, 801. Bernbaum, G. I. J. Am. Chem. Soc. 1974, 96, 6165. Peŕez-Salazar, A.; Cano, F. H.; Fayos, J.; Martinez-Carrera, S.; Garcia-Blanco, S. Acta Crystallogr. 1977, B33, 3525.
8. (a) Robins, D. J. Nat. Prod. Rep. 1993, 10, 487. Niwa, H.; Ogawa, T.; Okamoto, O.; Yamada, K. Tetrahedron 1992, 48, 10531.
9. (a) Robins, D. J. Nat. Prod. Rep. 1993, 10, 487. Niwa, H.; Ogawa, T.; Okamoto, O.; Yamada, K. Tetrahedron 1992, 48, 10531.
10. (b) Mattocks, A. R. Chemistry and Toxicology of Pyrrolizidine Alkaloids; Academic Press: London, 1986.
11. (c) Furuya, T.; Hikichi, M.; Iitaka, Y. Chem. Pharm. Bull. 1976, 24, 1120. Hikichi, M.; Furuya, T. Tetrahedron Lett. 1974, 3657. Mattocks, A. R.; White, I. N. H. Chem. Biol. Interact. 1971, 3, 383. Culvenor, C. C. J.; Edgar, J. A.; Smith, L. W.; Jago, M. V.; Peterson, J. E. Nature (London) New Biol. 1971, 229, 255. Schoental, R. Nature (London) 1970, 227, 401. Mattocks, A. R. Toxicol. Lett. 1982, 14, 111.
12. (c) Furuya, T.; Hikichi, M.; Iitaka, Y. Chem. Pharm. Bull. 1976, 24, 1120. Hikichi, M.; Furuya, T. Tetrahedron Lett. 1974, 3657. Mattocks, A. R.; White, I. N. H. Chem. Biol. Interact. 1971, 3, 383. Culvenor, C. C. J.; Edgar, J. A.; Smith, L. W.; Jago, M. V.; Peterson, J. E. Nature (London) New Biol. 1971, 229, 255. Schoental, R. Nature (London) 1970, 227, 401. Mattocks, A. R. Toxicol. Lett. 1982, 14, 111.
13. (c) Furuya, T.; Hikichi, M.; Iitaka, Y. Chem. Pharm. Bull. 1976, 24, 1120. Hikichi, M.; Furuya, T. Tetrahedron Lett. 1974, 3657. Mattocks, A. R.; White, I. N. H. Chem. Biol. Interact. 1971, 3, 383. Culvenor, C. C. J.; Edgar, J. A.; Smith, L. W.; Jago, M. V.; Peterson, J. E. Nature (London) New Biol. 1971, 229, 255. Schoental, R. Nature (London) 1970, 227, 401. Mattocks, A. R. Toxicol. Lett. 1982, 14, 111.
14. (c) Furuya, T.; Hikichi, M.; Iitaka, Y. Chem. Pharm. Bull. 1976, 24, 1120. Hikichi, M.; Furuya, T. Tetrahedron Lett. 1974, 3657. Mattocks, A. R.; White, I. N. H. Chem. Biol. Interact. 1971, 3, 383. Culvenor, C. C. J.; Edgar, J. A.; Smith, L. W.; Jago, M. V.; Peterson, J. E. Nature (London) New Biol. 1971, 229, 255. Schoental, R. Nature (London) 1970, 227, 401. Mattocks, A. R. Toxicol. Lett. 1982, 14, 111.
15. (c) Furuya, T.; Hikichi, M.; Iitaka, Y. Chem. Pharm. Bull. 1976, 24, 1120. Hikichi, M.; Furuya, T. Tetrahedron Lett. 1974, 3657. Mattocks, A. R.; White, I. N. H. Chem. Biol. Interact. 1971, 3, 383. Culvenor, C. C. J.; Edgar, J. A.; Smith, L. W.; Jago, M. V.; Peterson, J. E. Nature (London) New Biol. 1971, 229, 255. Schoental, R. Nature (London) 1970, 227, 401. Mattocks, A. R. Toxicol. Lett. 1982, 14, 111.
16. (c) Furuya, T.; Hikichi, M.; Iitaka, Y. Chem. Pharm. Bull. 1976, 24, 1120. Hikichi, M.; Furuya, T. Tetrahedron Lett. 1974, 3657. Mattocks, A. R.; White, I. N. H. Chem. Biol. Interact. 1971, 3, 383. Culvenor, C. C. J.; Edgar, J. A.; Smith, L. W.; Jago, M. V.; Peterson, J. E. Nature (London) New Biol. 1971, 229, 255. Schoental, R. Nature (London) 1970, 227, 401. Mattocks, A. R. Toxicol. Lett. 1982, 14, 111.
17. Yamada, K.; Niwa, H.; Uosaki, Y. Tetrahedron Lett. 1983, 24, 5731. Niwa, H.; Sakata, T.; Yamada, K. Bull. Chem. Soc. Jpn. 1994, 67, 2345.
18. Yamada, K.; Niwa, H.; Uosaki, Y. Tetrahedron Lett. 1983, 24, 5731. Niwa, H.; Sakata, T.; Yamada, K. Bull. Chem. Soc. Jpn. 1994, 67, 2345.
19. Vedejs, E.; Stults, J. S. J. Org. Chem. 1988, 53, 2226.
20. (a) For reviews, see: Metzner, P. Synthesis 1992, 1185. Weinreb, S. E.; Staib, R. R. Tetrahedron 1982, 38, 3087.
21. (a) For reviews, see: Metzner, P. Synthesis 1992, 1185. Weinreb, S. E.; Staib, R. R. Tetrahedron 1982, 38, 3087.
22. (b) Middleton, W. J. J. Org. Chem. 1965, 30, 1390. Yamada, K.; Yoshioka, M.; Sugiyama, N. J. Org. Chem. 1968, 33, 1240. Ohno, A.; Ohnishi, Y.; Tsuchihashi, G. Tetrahedron 1969, 25, 871. Katada, T.; Eguchi, S.; Esaki, T.; Sasaki, T. J. Chem. Soc., Perkin Trans. 1 1984, 1869. Katada, T.; Eguchi, S.; Esaki, T.; Sasaki, T. J. Chem. Soc., Perkin Trans. 1 1984, 2649. Bonini, B.; Mazzanti, G.; Zani, P.; Maccagnani, G. J. Chem. Soc., Perkin Trans. 1 1989, 2083. Schatz, J.; Sauer, J. Tetrahedron Lett. 1994, 35, 4767.
23. (b) Middleton, W. J. J. Org. Chem. 1965, 30, 1390. Yamada, K.; Yoshioka, M.; Sugiyama, N. J. Org. Chem. 1968, 33, 1240. Ohno, A.; Ohnishi, Y.; Tsuchihashi, G. Tetrahedron 1969, 25, 871. Katada, T.; Eguchi, S.; Esaki, T.; Sasaki, T. J. Chem. Soc., Perkin Trans. 1 1984, 1869. Katada, T.; Eguchi, S.; Esaki, T.; Sasaki, T. J. Chem. Soc., Perkin Trans. 1 1984, 2649. Bonini, B.; Mazzanti, G.; Zani, P.; Maccagnani, G. J. Chem. Soc., Perkin Trans. 1 1989, 2083. Schatz, J.; Sauer, J. Tetrahedron Lett. 1994, 35, 4767.
24. (b) Middleton, W. J. J. Org. Chem. 1965, 30, 1390. Yamada, K.; Yoshioka, M.; Sugiyama, N. J. Org. Chem. 1968, 33, 1240. Ohno, A.; Ohnishi, Y.; Tsuchihashi, G. Tetrahedron 1969, 25, 871. Katada, T.; Eguchi, S.; Esaki, T.; Sasaki, T. J. Chem. Soc., Perkin Trans. 1 1984, 1869. Katada, T.; Eguchi, S.; Esaki, T.; Sasaki, T. J. Chem. Soc., Perkin Trans. 1 1984, 2649. Bonini, B.; Mazzanti, G.; Zani, P.; Maccagnani, G. J. Chem. Soc., Perkin Trans. 1 1989, 2083. Schatz, J.; Sauer, J. Tetrahedron Lett. 1994, 35, 4767.
25. (b) Middleton, W. J. J. Org. Chem. 1965, 30, 1390. Yamada, K.; Yoshioka, M.; Sugiyama, N. J. Org. Chem. 1968, 33, 1240. Ohno, A.; Ohnishi, Y.; Tsuchihashi, G. Tetrahedron 1969, 25, 871. Katada, T.; Eguchi, S.; Esaki, T.; Sasaki, T. J. Chem. Soc., Perkin Trans. 1 1984, 1869. Katada, T.; Eguchi, S.; Esaki, T.; Sasaki, T. J. Chem. Soc., Perkin Trans. 1 1984, 2649. Bonini, B.; Mazzanti, G.; Zani, P.; Maccagnani, G. J. Chem. Soc., Perkin Trans. 1 1989, 2083. Schatz, J.; Sauer, J. Tetrahedron Lett. 1994, 35, 4767.
26. (b) Middleton, W. J. J. Org. Chem. 1965, 30, 1390. Yamada, K.; Yoshioka, M.; Sugiyama, N. J. Org. Chem. 1968, 33, 1240. Ohno, A.; Ohnishi, Y.; Tsuchihashi, G. Tetrahedron 1969, 25, 871. Katada, T.; Eguchi, S.; Esaki, T.; Sasaki, T. J. Chem. Soc., Perkin Trans. 1 1984, 1869. Katada, T.; Eguchi, S.; Esaki, T.; Sasaki, T. J. Chem. Soc., Perkin Trans. 1 1984, 2649. Bonini, B.; Mazzanti, G.; Zani, P.; Maccagnani, G. J. Chem. Soc., Perkin Trans. 1 1989, 2083. Schatz, J.; Sauer, J. Tetrahedron Lett. 1994, 35, 4767.
27. (b) Middleton, W. J. J. Org. Chem. 1965, 30, 1390. Yamada, K.; Yoshioka, M.; Sugiyama, N. J. Org. Chem. 1968, 33, 1240. Ohno, A.; Ohnishi, Y.; Tsuchihashi, G. Tetrahedron 1969, 25, 871. Katada, T.; Eguchi, S.; Esaki, T.; Sasaki, T. J. Chem. Soc., Perkin Trans. 1 1984, 1869. Katada, T.; Eguchi, S.; Esaki, T.; Sasaki, T. J. Chem. Soc., Perkin Trans. 1 1984, 2649. Bonini, B.; Mazzanti, G.; Zani, P.; Maccagnani, G. J. Chem. Soc., Perkin Trans. 1 1989, 2083. Schatz, J.; Sauer, J. Tetrahedron Lett. 1994, 35, 4767.
28. (b) Middleton, W. J. J. Org. Chem. 1965, 30, 1390. Yamada, K.; Yoshioka, M.; Sugiyama, N. J. Org. Chem. 1968, 33, 1240. Ohno, A.; Ohnishi, Y.; Tsuchihashi, G. Tetrahedron 1969, 25, 871. Katada, T.; Eguchi, S.; Esaki, T.; Sasaki, T. J. Chem. Soc., Perkin Trans. 1 1984, 1869. Katada, T.; Eguchi, S.; Esaki, T.; Sasaki, T. J. Chem. Soc., Perkin Trans. 1 1984, 2649. Bonini, B.; Mazzanti, G.; Zani, P.; Maccagnani, G. J. Chem. Soc., Perkin Trans. 1 1989, 2083. Schatz, J.; Sauer, J. Tetrahedron Lett. 1994, 35, 4767.
29. (c) Pinto, I. L.; Buckle, D. R.; Rami, H. K.; Smith, D. G. Tetrahedron Lett. 1992, 37, 7597.
30. Kirby, G. W.; Lochead, A. W. J. Chem. Soc., Chem. Commun. 1983, 1325. Bladon, C. M.; Ferguson, I. E. G.; Kirby, G. W.; Lochead, A. W.; McDougall, D. C. J. Chem. Soc., Perkin Trans. 1 1985, 1541.
31. Kirby, G. W.; Lochead, A. W. J. Chem. Soc., Chem. Commun. 1983, 1325. Bladon, C. M.; Ferguson, I. E. G.; Kirby, G. W.; Lochead, A. W.; McDougall, D. C. J. Chem. Soc., Perkin Trans. 1 1985, 1541.
32. (a) Vedejs, E.; Eberlein, T. H.; Mazur, D. J.; McClure, C. K.; Perry, D. A.; Ruggeri, R.; Schwartz, E.; Stults, J. S.; Varie, D. L.; Wilde, R. G.; Wittenberger, S. J. Org. Chem. 1986, 51, 1556.
33. (b) Vedejs, E.; Perry, D. A.; Houk, K. N.; Rondan, N. G. J. Am. Chem. Soc. 1983, 105, 6999.
34. (c) Chandrasekhar, J.; Ramamurthy, V.; Rao, V. P. J. Chem. Soc., Perkin Trans. 2 1988, 647. Barone, V.; Arnaud, R. Chem. Phys. Lett. 1996, 251, 393.
35. (c) Chandrasekhar, J.; Ramamurthy, V.; Rao, V. P. J. Chem. Soc., Perkin Trans. 2 1988, 647. Barone, V.; Arnaud, R. Chem. Phys. Lett. 1996, 251, 393.
36. Danishefsky, S.; Kitahara, T.; Schuda. P. F. Org. Synth. 1983, 61, 147.
37. Larsen, S. D.; Fisher, P. V.; Libby, B. E.; Jensen, R. M.; Mizsak, S. A.; Watt, W.; Ronk, W. R.; Hill, S. T. J. Org. Chem. 1996, 61, 4725.
38. Townsend, C. A.; Krol, W. J., Mao, S.; Steele, D. L. J. Org. Chem. 1991, 56, 728.
39. Tufariello, J. J.; Meckler, H.; Pushpananda, K.; Senaratne, A. Tetrahedron 1985, 41, 3447.
40. Volante, R. P. Tetrahedron Lett. 1981, 22, 3119.
41. Danishefsky, S. J.; Maring, C. J. J. Am. Chem. Soc. 1985, 107, 1269.
42. Shostakovskii, M. F.; Kuznetsov, N. V.; Che-min, Y. Dokl. Akad. Nauk SSSR 1961, 9, 1570.
43. Warren, S.; Earnshaw, C.; Wallis, C. J. J. Chem. Soc., Perkin Trans. 1 1979, 3099.
44. Caserio, M. C.; Kim, J. K.; Souma, Y.; Beutow, N.; Ibbeson, C. J. Org. Chem. 1989, 54, 1714.
45. Analogies: Pettit, G. R.; van Tamelen, E. E. Org. React. (N.Y.) 1962, 12, 356. Guziec, F.; Sanfilippo, L. J. Tetrahedron 1988, 44, 6241. de Mayo, P.; Nicholson, A. A. Isr. J. Chem. 1972, 10, 341. Omote, Y.; Yoshioka, M.; Yamada, K.; Sugiyama, N. J. Org. Chem. 1967, 32, 3676.
46. Analogies: Pettit, G. R.; van Tamelen, E. E. Org. React. (N.Y.) 1962, 12, 356. Guziec, F.; Sanfilippo, L. J. Tetrahedron 1988, 44, 6241. de Mayo, P.; Nicholson, A. A. Isr. J. Chem. 1972, 10, 341. Omote, Y.; Yoshioka, M.; Yamada, K.; Sugiyama, N. J. Org. Chem. 1967, 32, 3676.
47. Analogies: Pettit, G. R.; van Tamelen, E. E. Org. React. (N.Y.) 1962, 12, 356. Guziec, F.; Sanfilippo, L. J. Tetrahedron 1988, 44, 6241. de Mayo, P.; Nicholson, A. A. Isr. J. Chem. 1972, 10, 341. Omote, Y.; Yoshioka, M.; Yamada, K.; Sugiyama, N. J. Org. Chem. 1967, 32, 3676.
48. Analogies: Pettit, G. R.; van Tamelen, E. E. Org. React. (N.Y.) 1962, 12, 356. Guziec, F.; Sanfilippo, L. J. Tetrahedron 1988, 44, 6241. de Mayo, P.; Nicholson, A. A. Isr. J. Chem. 1972, 10, 341. Omote, Y.; Yoshioka, M.; Yamada, K.; Sugiyama, N. J. Org. Chem. 1967, 32, 3676.
49. Trost, B. M.; Braslau, R. J. Org. Chem. 1988, 53, 532.
50. Trost, B. M.; Leung, K. K. Tetrahedron Lett. 1975, 16, 4197.
51. Cooley, J. H.; Evain, E. J. Synthesis 1989, 1.
52. Noyori, R.; Murata, S.; Suzuki, M. Bull. Chem. Soc. Jpn. 1982, 55, 247.
53. Burgess, E. M.; Penton, H. R., Jr.; Taylor, E. A. J. Org Chem. 1973, 38, 26. Burgess, E. M.; Penton, H. R., Jr.; Taylor, E. A.; Williams, W. M. Org. Synth. 1977, 56, 40.
54. Burgess, E. M.; Penton, H. R., Jr.; Taylor, E. A. J. Org Chem. 1973, 38, 26. Burgess, E. M.; Penton, H. R., Jr.; Taylor, E. A.; Williams, W. M. Org. Synth. 1977, 56, 40.
55. 2 ABX pattern [δ 5.06 (1H, dd, J = 8.7, 4.5 Hz), 2.08 (1H, dd, 15.3, 8.7 Hz), 1.98 (1H, 15.3, 4.5 Hz)]. (Formula Presented)
56. (b) The low-temperature osmylation procedure was based on the following precedent where a chiral diamine is the accelerating ligand: Tomioka, K., Nakajuma, M.; Koga, K. J. Am. Chem. Soc. 1987, 109, 6213.
57. Vedejs, E.; Dent, W. H., III.; Gapinski, D. M.; McClure, C. K. J. Am. Chem. Soc. 1987, 109, 5437.
58. Corey, E. J.; Sarshar, S., Azimioara, Newbold, R. C.; Noe, M. C. J. Am. Chem. Soc. 1996, 118, 7851.
59. Kappor, R. C.; Mehrotra, R. N.; Vajpai, S. K.; Chaudhary, P. Trans. Met. Chem. 1991, 16, 65.
60. VanRheenen, V.; Kelly, R. C.; Chan, D. Y. Tetrahedron Lett. 1976. 17, 1973. Lohray, B. B.; Bhushan, V.; Kumar, R. K. J. Org. Chem. 1994, 59, 1375.
61. VanRheenen, V.; Kelly, R. C.; Chan, D. Y. Tetrahedron Lett. 1976. 17, 1973. Lohray, B. B.; Bhushan, V.; Kumar, R. K. J. Org. Chem. 1994, 59, 1375.
62. Minato, M.; Yamamoto, K.; Tsuji, J. J. Org. Chem. 1990, 55, 766.
63. Fuji, N.; Otaka, A.; Sugiyama, M.; Hatano, M.; Yajima, H. Chem. Pharm. Bull. 1987, 35, 3880.
64. Von Braun, J. Chem. Ber. 1910, 43, 1350.
65. Monzingo, R. Organic Syntheses; Wiley: New York, 1955; Collect. Vol. III, p 181.