Total synthesis of (-)-epibatidine using an asymmetric Diels-Alder reaction with a chiral n-acylnitroso dienophile

Journal of Organic Chemistry

Volumn 63, Issue 23, 1998, Pages 8397-8406

  Aoyagi, Sakae ^a   Tanaka, Ryuta ^a   Naruse, Masaichi ^a   Kibayashi, Chihiro ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EPIBATIDINE;

ARTICLE; BROMINATION; CHIRALITY; CYCLIZATION; DIASTEREOISOMER; FROG; HYDROGENATION; OXIDATION; SYNTHESIS;

EID: 0032514848     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9813078     Document Type: Article

References (93)

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22. For reviews on the total synthesis of epibatidine, see: (a) Szántay, C.; Kardos-Balogh, Z.; Szántay, C., Jr. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 1995; Vol. 46, pp 95-125. (b) Chen, Z.; Trudell, M. L. Chem. Rev. 1996, 96, 1179. (c) Kibayashi, C.; Aoyagi, S. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1997; Vol. 19, pp 66-81.
23. For the total synthesis of epibatidine, see: (a) Broka, C. A. Tetrahedron Lett. 1993, 34, 3251. (b) Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477. (c) Corey, E. J.; Loh, T.-P.; AchyuthaRao, S.; Daley, D. C.; Sarshar, S. J. Org. Chem. 1993, 58, 5600. (d) Clayton, S. C.; Regan, A. C. Tetrahedron Lett. 1993, 34, 7493. (e) Senokuchi, K.; Nakai, H.; Kawamura, M.; Katsube, N.; Nonaka, S.; Sawaragi, H.; Hamanaka, N. Synlett 1994, 343. (f) Szántay, C.; Kardos-Balogh, Z.; Moldvai, I.; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron Lett. 1994, 35, 3171. (g) Sestanj, K.; Melenski, E.; Jirkovsky, I. Tetrahedron Lett. 1994, 35, 5417. (h) Pandey, G.; Bagul, T. D.; Lakshmaiah, G. Tetrahedron Lett. 1994, 35, 7439. (i) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Romagnoli, R.; Zanirato, V. Tetrahedron Lett. 1994, 35, 9297. (j) Ko, S. Y.; Lerpiniere, J.; Linney, I. D.; Wrigglesworth, R. J. Chem. Soc., Chem. Commun. 1994, 1775. (k) Okabe, K.; Natsume, M. Chem. Pharm. Bull. Jpn. 1994, 42, 1432. (l) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (m) Xu, R.; Chu, G.; Bai, D. Tetrahedron Lett. 1996, 37, 1463. (n) Bai, D.; Xu, R.; Chu, G.; Zhu, X. J. Org. Chem. 1996, 61, 4600. (o) Zhang, C.; Trudell, M. L. J. Org. Chem. 1996, 61, 7189. (p) Trost, B. M.; Cook, G. R. Tetrahedron Lett. 1996, 37, 7485. (q) Szántay, C.; Kardos-Balogh, Z.; Moldvai, L; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron 1996, 52, 11053. (r) Giblin, G. M.; Jones, C. D.; Simpkins, N. S. Synlett 1997, 589.
24. For the total synthesis of epibatidine, see: (a) Broka, C. A. Tetrahedron Lett. 1993, 34, 3251. (b) Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477. (c) Corey, E. J.; Loh, T.-P.; AchyuthaRao, S.; Daley, D. C.; Sarshar, S. J. Org. Chem. 1993, 58, 5600. (d) Clayton, S. C.; Regan, A. C. Tetrahedron Lett. 1993, 34, 7493. (e) Senokuchi, K.; Nakai, H.; Kawamura, M.; Katsube, N.; Nonaka, S.; Sawaragi, H.; Hamanaka, N. Synlett 1994, 343. (f) Szántay, C.; Kardos-Balogh, Z.; Moldvai, I.; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron Lett. 1994, 35, 3171. (g) Sestanj, K.; Melenski, E.; Jirkovsky, I. Tetrahedron Lett. 1994, 35, 5417. (h) Pandey, G.; Bagul, T. D.; Lakshmaiah, G. Tetrahedron Lett. 1994, 35, 7439. (i) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Romagnoli, R.; Zanirato, V. Tetrahedron Lett. 1994, 35, 9297. (j) Ko, S. Y.; Lerpiniere, J.; Linney, I. D.; Wrigglesworth, R. J. Chem. Soc., Chem. Commun. 1994, 1775. (k) Okabe, K.; Natsume, M. Chem. Pharm. Bull. Jpn. 1994, 42, 1432. (l) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (m) Xu, R.; Chu, G.; Bai, D. Tetrahedron Lett. 1996, 37, 1463. (n) Bai, D.; Xu, R.; Chu, G.; Zhu, X. J. Org. Chem. 1996, 61, 4600. (o) Zhang, C.; Trudell, M. L. J. Org. Chem. 1996, 61, 7189. (p) Trost, B. M.; Cook, G. R. Tetrahedron Lett. 1996, 37, 7485. (q) Szántay, C.; Kardos-Balogh, Z.; Moldvai, L; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron 1996, 52, 11053. (r) Giblin, G. M.; Jones, C. D.; Simpkins, N. S. Synlett 1997, 589.
25. For the total synthesis of epibatidine, see: (a) Broka, C. A. Tetrahedron Lett. 1993, 34, 3251. (b) Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477. (c) Corey, E. J.; Loh, T.-P.; AchyuthaRao, S.; Daley, D. C.; Sarshar, S. J. Org. Chem. 1993, 58, 5600. (d) Clayton, S. C.; Regan, A. C. Tetrahedron Lett. 1993, 34, 7493. (e) Senokuchi, K.; Nakai, H.; Kawamura, M.; Katsube, N.; Nonaka, S.; Sawaragi, H.; Hamanaka, N. Synlett 1994, 343. (f) Szántay, C.; Kardos-Balogh, Z.; Moldvai, I.; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron Lett. 1994, 35, 3171. (g) Sestanj, K.; Melenski, E.; Jirkovsky, I. Tetrahedron Lett. 1994, 35, 5417. (h) Pandey, G.; Bagul, T. D.; Lakshmaiah, G. Tetrahedron Lett. 1994, 35, 7439. (i) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Romagnoli, R.; Zanirato, V. Tetrahedron Lett. 1994, 35, 9297. (j) Ko, S. Y.; Lerpiniere, J.; Linney, I. D.; Wrigglesworth, R. J. Chem. Soc., Chem. Commun. 1994, 1775. (k) Okabe, K.; Natsume, M. Chem. Pharm. Bull. Jpn. 1994, 42, 1432. (l) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (m) Xu, R.; Chu, G.; Bai, D. Tetrahedron Lett. 1996, 37, 1463. (n) Bai, D.; Xu, R.; Chu, G.; Zhu, X. J. Org. Chem. 1996, 61, 4600. (o) Zhang, C.; Trudell, M. L. J. Org. Chem. 1996, 61, 7189. (p) Trost, B. M.; Cook, G. R. Tetrahedron Lett. 1996, 37, 7485. (q) Szántay, C.; Kardos-Balogh, Z.; Moldvai, L; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron 1996, 52, 11053. (r) Giblin, G. M.; Jones, C. D.; Simpkins, N. S. Synlett 1997, 589.
26. For the total synthesis of epibatidine, see: (a) Broka, C. A. Tetrahedron Lett. 1993, 34, 3251. (b) Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477. (c) Corey, E. J.; Loh, T.-P.; AchyuthaRao, S.; Daley, D. C.; Sarshar, S. J. Org. Chem. 1993, 58, 5600. (d) Clayton, S. C.; Regan, A. C. Tetrahedron Lett. 1993, 34, 7493. (e) Senokuchi, K.; Nakai, H.; Kawamura, M.; Katsube, N.; Nonaka, S.; Sawaragi, H.; Hamanaka, N. Synlett 1994, 343. (f) Szántay, C.; Kardos-Balogh, Z.; Moldvai, I.; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron Lett. 1994, 35, 3171. (g) Sestanj, K.; Melenski, E.; Jirkovsky, I. Tetrahedron Lett. 1994, 35, 5417. (h) Pandey, G.; Bagul, T. D.; Lakshmaiah, G. Tetrahedron Lett. 1994, 35, 7439. (i) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Romagnoli, R.; Zanirato, V. Tetrahedron Lett. 1994, 35, 9297. (j) Ko, S. Y.; Lerpiniere, J.; Linney, I. D.; Wrigglesworth, R. J. Chem. Soc., Chem. Commun. 1994, 1775. (k) Okabe, K.; Natsume, M. Chem. Pharm. Bull. Jpn. 1994, 42, 1432. (l) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (m) Xu, R.; Chu, G.; Bai, D. Tetrahedron Lett. 1996, 37, 1463. (n) Bai, D.; Xu, R.; Chu, G.; Zhu, X. J. Org. Chem. 1996, 61, 4600. (o) Zhang, C.; Trudell, M. L. J. Org. Chem. 1996, 61, 7189. (p) Trost, B. M.; Cook, G. R. Tetrahedron Lett. 1996, 37, 7485. (q) Szántay, C.; Kardos-Balogh, Z.; Moldvai, L; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron 1996, 52, 11053. (r) Giblin, G. M.; Jones, C. D.; Simpkins, N. S. Synlett 1997, 589.
27. For the total synthesis of epibatidine, see: (a) Broka, C. A. Tetrahedron Lett. 1993, 34, 3251. (b) Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477. (c) Corey, E. J.; Loh, T.-P.; AchyuthaRao, S.; Daley, D. C.; Sarshar, S. J. Org. Chem. 1993, 58, 5600. (d) Clayton, S. C.; Regan, A. C. Tetrahedron Lett. 1993, 34, 7493. (e) Senokuchi, K.; Nakai, H.; Kawamura, M.; Katsube, N.; Nonaka, S.; Sawaragi, H.; Hamanaka, N. Synlett 1994, 343. (f) Szántay, C.; Kardos-Balogh, Z.; Moldvai, I.; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron Lett. 1994, 35, 3171. (g) Sestanj, K.; Melenski, E.; Jirkovsky, I. Tetrahedron Lett. 1994, 35, 5417. (h) Pandey, G.; Bagul, T. D.; Lakshmaiah, G. Tetrahedron Lett. 1994, 35, 7439. (i) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Romagnoli, R.; Zanirato, V. Tetrahedron Lett. 1994, 35, 9297. (j) Ko, S. Y.; Lerpiniere, J.; Linney, I. D.; Wrigglesworth, R. J. Chem. Soc., Chem. Commun. 1994, 1775. (k) Okabe, K.; Natsume, M. Chem. Pharm. Bull. Jpn. 1994, 42, 1432. (l) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (m) Xu, R.; Chu, G.; Bai, D. Tetrahedron Lett. 1996, 37, 1463. (n) Bai, D.; Xu, R.; Chu, G.; Zhu, X. J. Org. Chem. 1996, 61, 4600. (o) Zhang, C.; Trudell, M. L. J. Org. Chem. 1996, 61, 7189. (p) Trost, B. M.; Cook, G. R. Tetrahedron Lett. 1996, 37, 7485. (q) Szántay, C.; Kardos-Balogh, Z.; Moldvai, L; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron 1996, 52, 11053. (r) Giblin, G. M.; Jones, C. D.; Simpkins, N. S. Synlett 1997, 589.
28. For the total synthesis of epibatidine, see: (a) Broka, C. A. Tetrahedron Lett. 1993, 34, 3251. (b) Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477. (c) Corey, E. J.; Loh, T.-P.; AchyuthaRao, S.; Daley, D. C.; Sarshar, S. J. Org. Chem. 1993, 58, 5600. (d) Clayton, S. C.; Regan, A. C. Tetrahedron Lett. 1993, 34, 7493. (e) Senokuchi, K.; Nakai, H.; Kawamura, M.; Katsube, N.; Nonaka, S.; Sawaragi, H.; Hamanaka, N. Synlett 1994, 343. (f) Szántay, C.; Kardos-Balogh, Z.; Moldvai, I.; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron Lett. 1994, 35, 3171. (g) Sestanj, K.; Melenski, E.; Jirkovsky, I. Tetrahedron Lett. 1994, 35, 5417. (h) Pandey, G.; Bagul, T. D.; Lakshmaiah, G. Tetrahedron Lett. 1994, 35, 7439. (i) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Romagnoli, R.; Zanirato, V. Tetrahedron Lett. 1994, 35, 9297. (j) Ko, S. Y.; Lerpiniere, J.; Linney, I. D.; Wrigglesworth, R. J. Chem. Soc., Chem. Commun. 1994, 1775. (k) Okabe, K.; Natsume, M. Chem. Pharm. Bull. Jpn. 1994, 42, 1432. (l) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (m) Xu, R.; Chu, G.; Bai, D. Tetrahedron Lett. 1996, 37, 1463. (n) Bai, D.; Xu, R.; Chu, G.; Zhu, X. J. Org. Chem. 1996, 61, 4600. (o) Zhang, C.; Trudell, M. L. J. Org. Chem. 1996, 61, 7189. (p) Trost, B. M.; Cook, G. R. Tetrahedron Lett. 1996, 37, 7485. (q) Szántay, C.; Kardos-Balogh, Z.; Moldvai, L; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron 1996, 52, 11053. (r) Giblin, G. M.; Jones, C. D.; Simpkins, N. S. Synlett 1997, 589.
29. For the total synthesis of epibatidine, see: (a) Broka, C. A. Tetrahedron Lett. 1993, 34, 3251. (b) Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477. (c) Corey, E. J.; Loh, T.-P.; AchyuthaRao, S.; Daley, D. C.; Sarshar, S. J. Org. Chem. 1993, 58, 5600. (d) Clayton, S. C.; Regan, A. C. Tetrahedron Lett. 1993, 34, 7493. (e) Senokuchi, K.; Nakai, H.; Kawamura, M.; Katsube, N.; Nonaka, S.; Sawaragi, H.; Hamanaka, N. Synlett 1994, 343. (f) Szántay, C.; Kardos-Balogh, Z.; Moldvai, I.; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron Lett. 1994, 35, 3171. (g) Sestanj, K.; Melenski, E.; Jirkovsky, I. Tetrahedron Lett. 1994, 35, 5417. (h) Pandey, G.; Bagul, T. D.; Lakshmaiah, G. Tetrahedron Lett. 1994, 35, 7439. (i) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Romagnoli, R.; Zanirato, V. Tetrahedron Lett. 1994, 35, 9297. (j) Ko, S. Y.; Lerpiniere, J.; Linney, I. D.; Wrigglesworth, R. J. Chem. Soc., Chem. Commun. 1994, 1775. (k) Okabe, K.; Natsume, M. Chem. Pharm. Bull. Jpn. 1994, 42, 1432. (l) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (m) Xu, R.; Chu, G.; Bai, D. Tetrahedron Lett. 1996, 37, 1463. (n) Bai, D.; Xu, R.; Chu, G.; Zhu, X. J. Org. Chem. 1996, 61, 4600. (o) Zhang, C.; Trudell, M. L. J. Org. Chem. 1996, 61, 7189. (p) Trost, B. M.; Cook, G. R. Tetrahedron Lett. 1996, 37, 7485. (q) Szántay, C.; Kardos-Balogh, Z.; Moldvai, L; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron 1996, 52, 11053. (r) Giblin, G. M.; Jones, C. D.; Simpkins, N. S. Synlett 1997, 589.
30. For the total synthesis of epibatidine, see: (a) Broka, C. A. Tetrahedron Lett. 1993, 34, 3251. (b) Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477. (c) Corey, E. J.; Loh, T.-P.; AchyuthaRao, S.; Daley, D. C.; Sarshar, S. J. Org. Chem. 1993, 58, 5600. (d) Clayton, S. C.; Regan, A. C. Tetrahedron Lett. 1993, 34, 7493. (e) Senokuchi, K.; Nakai, H.; Kawamura, M.; Katsube, N.; Nonaka, S.; Sawaragi, H.; Hamanaka, N. Synlett 1994, 343. (f) Szántay, C.; Kardos-Balogh, Z.; Moldvai, I.; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron Lett. 1994, 35, 3171. (g) Sestanj, K.; Melenski, E.; Jirkovsky, I. Tetrahedron Lett. 1994, 35, 5417. (h) Pandey, G.; Bagul, T. D.; Lakshmaiah, G. Tetrahedron Lett. 1994, 35, 7439. (i) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Romagnoli, R.; Zanirato, V. Tetrahedron Lett. 1994, 35, 9297. (j) Ko, S. Y.; Lerpiniere, J.; Linney, I. D.; Wrigglesworth, R. J. Chem. Soc., Chem. Commun. 1994, 1775. (k) Okabe, K.; Natsume, M. Chem. Pharm. Bull. Jpn. 1994, 42, 1432. (l) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (m) Xu, R.; Chu, G.; Bai, D. Tetrahedron Lett. 1996, 37, 1463. (n) Bai, D.; Xu, R.; Chu, G.; Zhu, X. J. Org. Chem. 1996, 61, 4600. (o) Zhang, C.; Trudell, M. L. J. Org. Chem. 1996, 61, 7189. (p) Trost, B. M.; Cook, G. R. Tetrahedron Lett. 1996, 37, 7485. (q) Szántay, C.; Kardos-Balogh, Z.; Moldvai, L; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron 1996, 52, 11053. (r) Giblin, G. M.; Jones, C. D.; Simpkins, N. S. Synlett 1997, 589.
31. For the total synthesis of epibatidine, see: (a) Broka, C. A. Tetrahedron Lett. 1993, 34, 3251. (b) Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477. (c) Corey, E. J.; Loh, T.-P.; AchyuthaRao, S.; Daley, D. C.; Sarshar, S. J. Org. Chem. 1993, 58, 5600. (d) Clayton, S. C.; Regan, A. C. Tetrahedron Lett. 1993, 34, 7493. (e) Senokuchi, K.; Nakai, H.; Kawamura, M.; Katsube, N.; Nonaka, S.; Sawaragi, H.; Hamanaka, N. Synlett 1994, 343. (f) Szántay, C.; Kardos-Balogh, Z.; Moldvai, I.; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron Lett. 1994, 35, 3171. (g) Sestanj, K.; Melenski, E.; Jirkovsky, I. Tetrahedron Lett. 1994, 35, 5417. (h) Pandey, G.; Bagul, T. D.; Lakshmaiah, G. Tetrahedron Lett. 1994, 35, 7439. (i) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Romagnoli, R.; Zanirato, V. Tetrahedron Lett. 1994, 35, 9297. (j) Ko, S. Y.; Lerpiniere, J.; Linney, I. D.; Wrigglesworth, R. J. Chem. Soc., Chem. Commun. 1994, 1775. (k) Okabe, K.; Natsume, M. Chem. Pharm. Bull. Jpn. 1994, 42, 1432. (l) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (m) Xu, R.; Chu, G.; Bai, D. Tetrahedron Lett. 1996, 37, 1463. (n) Bai, D.; Xu, R.; Chu, G.; Zhu, X. J. Org. Chem. 1996, 61, 4600. (o) Zhang, C.; Trudell, M. L. J. Org. Chem. 1996, 61, 7189. (p) Trost, B. M.; Cook, G. R. Tetrahedron Lett. 1996, 37, 7485. (q) Szántay, C.; Kardos-Balogh, Z.; Moldvai, L; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron 1996, 52, 11053. (r) Giblin, G. M.; Jones, C. D.; Simpkins, N. S. Synlett 1997, 589.
32. For the total synthesis of epibatidine, see: (a) Broka, C. A. Tetrahedron Lett. 1993, 34, 3251. (b) Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477. (c) Corey, E. J.; Loh, T.-P.; AchyuthaRao, S.; Daley, D. C.; Sarshar, S. J. Org. Chem. 1993, 58, 5600. (d) Clayton, S. C.; Regan, A. C. Tetrahedron Lett. 1993, 34, 7493. (e) Senokuchi, K.; Nakai, H.; Kawamura, M.; Katsube, N.; Nonaka, S.; Sawaragi, H.; Hamanaka, N. Synlett 1994, 343. (f) Szántay, C.; Kardos-Balogh, Z.; Moldvai, I.; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron Lett. 1994, 35, 3171. (g) Sestanj, K.; Melenski, E.; Jirkovsky, I. Tetrahedron Lett. 1994, 35, 5417. (h) Pandey, G.; Bagul, T. D.; Lakshmaiah, G. Tetrahedron Lett. 1994, 35, 7439. (i) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Romagnoli, R.; Zanirato, V. Tetrahedron Lett. 1994, 35, 9297. (j) Ko, S. Y.; Lerpiniere, J.; Linney, I. D.; Wrigglesworth, R. J. Chem. Soc., Chem. Commun. 1994, 1775. (k) Okabe, K.; Natsume, M. Chem. Pharm. Bull. Jpn. 1994, 42, 1432. (l) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (m) Xu, R.; Chu, G.; Bai, D. Tetrahedron Lett. 1996, 37, 1463. (n) Bai, D.; Xu, R.; Chu, G.; Zhu, X. J. Org. Chem. 1996, 61, 4600. (o) Zhang, C.; Trudell, M. L. J. Org. Chem. 1996, 61, 7189. (p) Trost, B. M.; Cook, G. R. Tetrahedron Lett. 1996, 37, 7485. (q) Szántay, C.; Kardos-Balogh, Z.; Moldvai, L; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron 1996, 52, 11053. (r) Giblin, G. M.; Jones, C. D.; Simpkins, N. S. Synlett 1997, 589.
33. For the total synthesis of epibatidine, see: (a) Broka, C. A. Tetrahedron Lett. 1993, 34, 3251. (b) Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477. (c) Corey, E. J.; Loh, T.-P.; AchyuthaRao, S.; Daley, D. C.; Sarshar, S. J. Org. Chem. 1993, 58, 5600. (d) Clayton, S. C.; Regan, A. C. Tetrahedron Lett. 1993, 34, 7493. (e) Senokuchi, K.; Nakai, H.; Kawamura, M.; Katsube, N.; Nonaka, S.; Sawaragi, H.; Hamanaka, N. Synlett 1994, 343. (f) Szántay, C.; Kardos-Balogh, Z.; Moldvai, I.; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron Lett. 1994, 35, 3171. (g) Sestanj, K.; Melenski, E.; Jirkovsky, I. Tetrahedron Lett. 1994, 35, 5417. (h) Pandey, G.; Bagul, T. D.; Lakshmaiah, G. Tetrahedron Lett. 1994, 35, 7439. (i) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Romagnoli, R.; Zanirato, V. Tetrahedron Lett. 1994, 35, 9297. (j) Ko, S. Y.; Lerpiniere, J.; Linney, I. D.; Wrigglesworth, R. J. Chem. Soc., Chem. Commun. 1994, 1775. (k) Okabe, K.; Natsume, M. Chem. Pharm. Bull. Jpn. 1994, 42, 1432. (l) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (m) Xu, R.; Chu, G.; Bai, D. Tetrahedron Lett. 1996, 37, 1463. (n) Bai, D.; Xu, R.; Chu, G.; Zhu, X. J. Org. Chem. 1996, 61, 4600. (o) Zhang, C.; Trudell, M. L. J. Org. Chem. 1996, 61, 7189. (p) Trost, B. M.; Cook, G. R. Tetrahedron Lett. 1996, 37, 7485. (q) Szántay, C.; Kardos-Balogh, Z.; Moldvai, L; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron 1996, 52, 11053. (r) Giblin, G. M.; Jones, C. D.; Simpkins, N. S. Synlett 1997, 589.
34. For the total synthesis of epibatidine, see: (a) Broka, C. A. Tetrahedron Lett. 1993, 34, 3251. (b) Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477. (c) Corey, E. J.; Loh, T.-P.; AchyuthaRao, S.; Daley, D. C.; Sarshar, S. J. Org. Chem. 1993, 58, 5600. (d) Clayton, S. C.; Regan, A. C. Tetrahedron Lett. 1993, 34, 7493. (e) Senokuchi, K.; Nakai, H.; Kawamura, M.; Katsube, N.; Nonaka, S.; Sawaragi, H.; Hamanaka, N. Synlett 1994, 343. (f) Szántay, C.; Kardos-Balogh, Z.; Moldvai, I.; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron Lett. 1994, 35, 3171. (g) Sestanj, K.; Melenski, E.; Jirkovsky, I. Tetrahedron Lett. 1994, 35, 5417. (h) Pandey, G.; Bagul, T. D.; Lakshmaiah, G. Tetrahedron Lett. 1994, 35, 7439. (i) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Romagnoli, R.; Zanirato, V. Tetrahedron Lett. 1994, 35, 9297. (j) Ko, S. Y.; Lerpiniere, J.; Linney, I. D.; Wrigglesworth, R. J. Chem. Soc., Chem. Commun. 1994, 1775. (k) Okabe, K.; Natsume, M. Chem. Pharm. Bull. Jpn. 1994, 42, 1432. (l) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (m) Xu, R.; Chu, G.; Bai, D. Tetrahedron Lett. 1996, 37, 1463. (n) Bai, D.; Xu, R.; Chu, G.; Zhu, X. J. Org. Chem. 1996, 61, 4600. (o) Zhang, C.; Trudell, M. L. J. Org. Chem. 1996, 61, 7189. (p) Trost, B. M.; Cook, G. R. Tetrahedron Lett. 1996, 37, 7485. (q) Szántay, C.; Kardos-Balogh, Z.; Moldvai, L; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron 1996, 52, 11053. (r) Giblin, G. M.; Jones, C. D.; Simpkins, N. S. Synlett 1997, 589.
35. For the total synthesis of epibatidine, see: (a) Broka, C. A. Tetrahedron Lett. 1993, 34, 3251. (b) Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477. (c) Corey, E. J.; Loh, T.-P.; AchyuthaRao, S.; Daley, D. C.; Sarshar, S. J. Org. Chem. 1993, 58, 5600. (d) Clayton, S. C.; Regan, A. C. Tetrahedron Lett. 1993, 34, 7493. (e) Senokuchi, K.; Nakai, H.; Kawamura, M.; Katsube, N.; Nonaka, S.; Sawaragi, H.; Hamanaka, N. Synlett 1994, 343. (f) Szántay, C.; Kardos-Balogh, Z.; Moldvai, I.; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron Lett. 1994, 35, 3171. (g) Sestanj, K.; Melenski, E.; Jirkovsky, I. Tetrahedron Lett. 1994, 35, 5417. (h) Pandey, G.; Bagul, T. D.; Lakshmaiah, G. Tetrahedron Lett. 1994, 35, 7439. (i) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Romagnoli, R.; Zanirato, V. Tetrahedron Lett. 1994, 35, 9297. (j) Ko, S. Y.; Lerpiniere, J.; Linney, I. D.; Wrigglesworth, R. J. Chem. Soc., Chem. Commun. 1994, 1775. (k) Okabe, K.; Natsume, M. Chem. Pharm. Bull. Jpn. 1994, 42, 1432. (l) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (m) Xu, R.; Chu, G.; Bai, D. Tetrahedron Lett. 1996, 37, 1463. (n) Bai, D.; Xu, R.; Chu, G.; Zhu, X. J. Org. Chem. 1996, 61, 4600. (o) Zhang, C.; Trudell, M. L. J. Org. Chem. 1996, 61, 7189. (p) Trost, B. M.; Cook, G. R. Tetrahedron Lett. 1996, 37, 7485. (q) Szántay, C.; Kardos-Balogh, Z.; Moldvai, L; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron 1996, 52, 11053. (r) Giblin, G. M.; Jones, C. D.; Simpkins, N. S. Synlett 1997, 589.
36. For the total synthesis of epibatidine, see: (a) Broka, C. A. Tetrahedron Lett. 1993, 34, 3251. (b) Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477. (c) Corey, E. J.; Loh, T.-P.; AchyuthaRao, S.; Daley, D. C.; Sarshar, S. J. Org. Chem. 1993, 58, 5600. (d) Clayton, S. C.; Regan, A. C. Tetrahedron Lett. 1993, 34, 7493. (e) Senokuchi, K.; Nakai, H.; Kawamura, M.; Katsube, N.; Nonaka, S.; Sawaragi, H.; Hamanaka, N. Synlett 1994, 343. (f) Szántay, C.; Kardos-Balogh, Z.; Moldvai, I.; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron Lett. 1994, 35, 3171. (g) Sestanj, K.; Melenski, E.; Jirkovsky, I. Tetrahedron Lett. 1994, 35, 5417. (h) Pandey, G.; Bagul, T. D.; Lakshmaiah, G. Tetrahedron Lett. 1994, 35, 7439. (i) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Romagnoli, R.; Zanirato, V. Tetrahedron Lett. 1994, 35, 9297. (j) Ko, S. Y.; Lerpiniere, J.; Linney, I. D.; Wrigglesworth, R. J. Chem. Soc., Chem. Commun. 1994, 1775. (k) Okabe, K.; Natsume, M. Chem. Pharm. Bull. Jpn. 1994, 42, 1432. (l) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (m) Xu, R.; Chu, G.; Bai, D. Tetrahedron Lett. 1996, 37, 1463. (n) Bai, D.; Xu, R.; Chu, G.; Zhu, X. J. Org. Chem. 1996, 61, 4600. (o) Zhang, C.; Trudell, M. L. J. Org. Chem. 1996, 61, 7189. (p) Trost, B. M.; Cook, G. R. Tetrahedron Lett. 1996, 37, 7485. (q) Szántay, C.; Kardos-Balogh, Z.; Moldvai, L; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron 1996, 52, 11053. (r) Giblin, G. M.; Jones, C. D.; Simpkins, N. S. Synlett 1997, 589.
37. For the total synthesis of epibatidine, see: (a) Broka, C. A. Tetrahedron Lett. 1993, 34, 3251. (b) Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477. (c) Corey, E. J.; Loh, T.-P.; AchyuthaRao, S.; Daley, D. C.; Sarshar, S. J. Org. Chem. 1993, 58, 5600. (d) Clayton, S. C.; Regan, A. C. Tetrahedron Lett. 1993, 34, 7493. (e) Senokuchi, K.; Nakai, H.; Kawamura, M.; Katsube, N.; Nonaka, S.; Sawaragi, H.; Hamanaka, N. Synlett 1994, 343. (f) Szántay, C.; Kardos-Balogh, Z.; Moldvai, I.; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron Lett. 1994, 35, 3171. (g) Sestanj, K.; Melenski, E.; Jirkovsky, I. Tetrahedron Lett. 1994, 35, 5417. (h) Pandey, G.; Bagul, T. D.; Lakshmaiah, G. Tetrahedron Lett. 1994, 35, 7439. (i) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Romagnoli, R.; Zanirato, V. Tetrahedron Lett. 1994, 35, 9297. (j) Ko, S. Y.; Lerpiniere, J.; Linney, I. D.; Wrigglesworth, R. J. Chem. Soc., Chem. Commun. 1994, 1775. (k) Okabe, K.; Natsume, M. Chem. Pharm. Bull. Jpn. 1994, 42, 1432. (l) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (m) Xu, R.; Chu, G.; Bai, D. Tetrahedron Lett. 1996, 37, 1463. (n) Bai, D.; Xu, R.; Chu, G.; Zhu, X. J. Org. Chem. 1996, 61, 4600. (o) Zhang, C.; Trudell, M. L. J. Org. Chem. 1996, 61, 7189. (p) Trost, B. M.; Cook, G. R. Tetrahedron Lett. 1996, 37, 7485. (q) Szántay, C.; Kardos-Balogh, Z.; Moldvai, L; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron 1996, 52, 11053. (r) Giblin, G. M.; Jones, C. D.; Simpkins, N. S. Synlett 1997, 589.
38. For the total synthesis of epibatidine, see: (a) Broka, C. A. Tetrahedron Lett. 1993, 34, 3251. (b) Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477. (c) Corey, E. J.; Loh, T.-P.; AchyuthaRao, S.; Daley, D. C.; Sarshar, S. J. Org. Chem. 1993, 58, 5600. (d) Clayton, S. C.; Regan, A. C. Tetrahedron Lett. 1993, 34, 7493. (e) Senokuchi, K.; Nakai, H.; Kawamura, M.; Katsube, N.; Nonaka, S.; Sawaragi, H.; Hamanaka, N. Synlett 1994, 343. (f) Szántay, C.; Kardos-Balogh, Z.; Moldvai, I.; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron Lett. 1994, 35, 3171. (g) Sestanj, K.; Melenski, E.; Jirkovsky, I. Tetrahedron Lett. 1994, 35, 5417. (h) Pandey, G.; Bagul, T. D.; Lakshmaiah, G. Tetrahedron Lett. 1994, 35, 7439. (i) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Romagnoli, R.; Zanirato, V. Tetrahedron Lett. 1994, 35, 9297. (j) Ko, S. Y.; Lerpiniere, J.; Linney, I. D.; Wrigglesworth, R. J. Chem. Soc., Chem. Commun. 1994, 1775. (k) Okabe, K.; Natsume, M. Chem. Pharm. Bull. Jpn. 1994, 42, 1432. (l) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (m) Xu, R.; Chu, G.; Bai, D. Tetrahedron Lett. 1996, 37, 1463. (n) Bai, D.; Xu, R.; Chu, G.; Zhu, X. J. Org. Chem. 1996, 61, 4600. (o) Zhang, C.; Trudell, M. L. J. Org. Chem. 1996, 61, 7189. (p) Trost, B. M.; Cook, G. R. Tetrahedron Lett. 1996, 37, 7485. (q) Szántay, C.; Kardos-Balogh, Z.; Moldvai, L; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron 1996, 52, 11053. (r) Giblin, G. M.; Jones, C. D.; Simpkins, N. S. Synlett 1997, 589.
39. For the total synthesis of epibatidine, see: (a) Broka, C. A. Tetrahedron Lett. 1993, 34, 3251. (b) Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477. (c) Corey, E. J.; Loh, T.-P.; AchyuthaRao, S.; Daley, D. C.; Sarshar, S. J. Org. Chem. 1993, 58, 5600. (d) Clayton, S. C.; Regan, A. C. Tetrahedron Lett. 1993, 34, 7493. (e) Senokuchi, K.; Nakai, H.; Kawamura, M.; Katsube, N.; Nonaka, S.; Sawaragi, H.; Hamanaka, N. Synlett 1994, 343. (f) Szántay, C.; Kardos-Balogh, Z.; Moldvai, I.; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron Lett. 1994, 35, 3171. (g) Sestanj, K.; Melenski, E.; Jirkovsky, I. Tetrahedron Lett. 1994, 35, 5417. (h) Pandey, G.; Bagul, T. D.; Lakshmaiah, G. Tetrahedron Lett. 1994, 35, 7439. (i) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Romagnoli, R.; Zanirato, V. Tetrahedron Lett. 1994, 35, 9297. (j) Ko, S. Y.; Lerpiniere, J.; Linney, I. D.; Wrigglesworth, R. J. Chem. Soc., Chem. Commun. 1994, 1775. (k) Okabe, K.; Natsume, M. Chem. Pharm. Bull. Jpn. 1994, 42, 1432. (l) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (m) Xu, R.; Chu, G.; Bai, D. Tetrahedron Lett. 1996, 37, 1463. (n) Bai, D.; Xu, R.; Chu, G.; Zhu, X. J. Org. Chem. 1996, 61, 4600. (o) Zhang, C.; Trudell, M. L. J. Org. Chem. 1996, 61, 7189. (p) Trost, B. M.; Cook, G. R. Tetrahedron Lett. 1996, 37, 7485. (q) Szántay, C.; Kardos-Balogh, Z.; Moldvai, L; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron 1996, 52, 11053. (r) Giblin, G. M.; Jones, C. D.; Simpkins, N. S. Synlett 1997, 589.
40. For the total synthesis of epibatidine, see: (a) Broka, C. A. Tetrahedron Lett. 1993, 34, 3251. (b) Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477. (c) Corey, E. J.; Loh, T.-P.; AchyuthaRao, S.; Daley, D. C.; Sarshar, S. J. Org. Chem. 1993, 58, 5600. (d) Clayton, S. C.; Regan, A. C. Tetrahedron Lett. 1993, 34, 7493. (e) Senokuchi, K.; Nakai, H.; Kawamura, M.; Katsube, N.; Nonaka, S.; Sawaragi, H.; Hamanaka, N. Synlett 1994, 343. (f) Szántay, C.; Kardos-Balogh, Z.; Moldvai, I.; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron Lett. 1994, 35, 3171. (g) Sestanj, K.; Melenski, E.; Jirkovsky, I. Tetrahedron Lett. 1994, 35, 5417. (h) Pandey, G.; Bagul, T. D.; Lakshmaiah, G. Tetrahedron Lett. 1994, 35, 7439. (i) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Romagnoli, R.; Zanirato, V. Tetrahedron Lett. 1994, 35, 9297. (j) Ko, S. Y.; Lerpiniere, J.; Linney, I. D.; Wrigglesworth, R. J. Chem. Soc., Chem. Commun. 1994, 1775. (k) Okabe, K.; Natsume, M. Chem. Pharm. Bull. Jpn. 1994, 42, 1432. (l) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (m) Xu, R.; Chu, G.; Bai, D. Tetrahedron Lett. 1996, 37, 1463. (n) Bai, D.; Xu, R.; Chu, G.; Zhu, X. J. Org. Chem. 1996, 61, 4600. (o) Zhang, C.; Trudell, M. L. J. Org. Chem. 1996, 61, 7189. (p) Trost, B. M.; Cook, G. R. Tetrahedron Lett. 1996, 37, 7485. (q) Szántay, C.; Kardos-Balogh, Z.; Moldvai, L; Szántay, C., Jr.; Temesvári-Major, E.; Blaskó, G. Tetrahedron 1996, 52, 11053. (r) Giblin, G. M.; Jones, C. D.; Simpkins, N. S. Synlett 1997, 589.
41. (s) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. Chem. Commun. 1997, 1857. (t) Pavri, N. P.; Trudell, M. L. Tetrahedron Lett. 1997, 38, 7993. (u) Jones, C. D.; Simpkins, N. S.; Giblin, G. M. Tetrahedron Lett. 1998, 39, 1023. (v) Pandey, G.; Bagul, T. D.; Sahoo, A. K J. Org. Chem. 1998, 63, 760. (w) Sirisoma, N. S.; Johnson, C. R. Tetrahedron Lett. 1998, 39, 2059. See also ref 3.
42. (s) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. Chem. Commun. 1997, 1857. (t) Pavri, N. P.; Trudell, M. L. Tetrahedron Lett. 1997, 38, 7993. (u) Jones, C. D.; Simpkins, N. S.; Giblin, G. M. Tetrahedron Lett. 1998, 39, 1023. (v) Pandey, G.; Bagul, T. D.; Sahoo, A. K J. Org. Chem. 1998, 63, 760. (w) Sirisoma, N. S.; Johnson, C. R. Tetrahedron Lett. 1998, 39, 2059. See also ref 3.
43. (s) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. Chem. Commun. 1997, 1857. (t) Pavri, N. P.; Trudell, M. L. Tetrahedron Lett. 1997, 38, 7993. (u) Jones, C. D.; Simpkins, N. S.; Giblin, G. M. Tetrahedron Lett. 1998, 39, 1023. (v) Pandey, G.; Bagul, T. D.; Sahoo, A. K J. Org. Chem. 1998, 63, 760. (w) Sirisoma, N. S.; Johnson, C. R. Tetrahedron Lett. 1998, 39, 2059. See also ref 3.
44. (s) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. Chem. Commun. 1997, 1857. (t) Pavri, N. P.; Trudell, M. L. Tetrahedron Lett. 1997, 38, 7993. (u) Jones, C. D.; Simpkins, N. S.; Giblin, G. M. Tetrahedron Lett. 1998, 39, 1023. (v) Pandey, G.; Bagul, T. D.; Sahoo, A. K J. Org. Chem. 1998, 63, 760. (w) Sirisoma, N. S.; Johnson, C. R. Tetrahedron Lett. 1998, 39, 2059. See also ref 3.
45. (s) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. Chem. Commun. 1997, 1857. (t) Pavri, N. P.; Trudell, M. L. Tetrahedron Lett. 1997, 38, 7993. (u) Jones, C. D.; Simpkins, N. S.; Giblin, G. M. Tetrahedron Lett. 1998, 39, 1023. (v) Pandey, G.; Bagul, T. D.; Sahoo, A. K J. Org. Chem. 1998, 63, 760. (w) Sirisoma, N. S.; Johnson, C. R. Tetrahedron Lett. 1998, 39, 2059. See also ref 3.
46. For formal synthesis of epibatidine, see: (a) Hernández, A.; Marcos, M.; Rapoport, H. J. Org. Chem. 1995, 60, 2683. (b) Davis, C. R.; Johnson, R. A.; Cialdella, J. I.; Liggett, W. F.; Mizsak, S. A.; Marshall, V. P. J. Org. Chem. 1997, 62, 2244. (c) Singh, S.; Basmadjian, G. P. Tetrahedron Lett. 1997, 38, 6829. (d) Ikeda, M.; Kugo, Y.; Kondo, Y.; Yamazaki, T.; Sato, T. J. Chem. Soc., Perkin Trans. 1 1997, 3339. (e) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Tetrahedron 1977, 53, 17177. (f) Clive, D. L. J.; Yeh, V. S. C. Tetrahedron Lett. 1998, 39, 4789.
47. For formal synthesis of epibatidine, see: (a) Hernández, A.; Marcos, M.; Rapoport, H. J. Org. Chem. 1995, 60, 2683. (b) Davis, C. R.; Johnson, R. A.; Cialdella, J. I.; Liggett, W. F.; Mizsak, S. A.; Marshall, V. P. J. Org. Chem. 1997, 62, 2244. (c) Singh, S.; Basmadjian, G. P. Tetrahedron Lett. 1997, 38, 6829. (d) Ikeda, M.; Kugo, Y.; Kondo, Y.; Yamazaki, T.; Sato, T. J. Chem. Soc., Perkin Trans. 1 1997, 3339. (e) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Tetrahedron 1977, 53, 17177. (f) Clive, D. L. J.; Yeh, V. S. C. Tetrahedron Lett. 1998, 39, 4789.
48. For formal synthesis of epibatidine, see: (a) Hernández, A.; Marcos, M.; Rapoport, H. J. Org. Chem. 1995, 60, 2683. (b) Davis, C. R.; Johnson, R. A.; Cialdella, J. I.; Liggett, W. F.; Mizsak, S. A.; Marshall, V. P. J. Org. Chem. 1997, 62, 2244. (c) Singh, S.; Basmadjian, G. P. Tetrahedron Lett. 1997, 38, 6829. (d) Ikeda, M.; Kugo, Y.; Kondo, Y.; Yamazaki, T.; Sato, T. J. Chem. Soc., Perkin Trans. 1 1997, 3339. (e) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Tetrahedron 1977, 53, 17177. (f) Clive, D. L. J.; Yeh, V. S. C. Tetrahedron Lett. 1998, 39, 4789.
49. For formal synthesis of epibatidine, see: (a) Hernández, A.; Marcos, M.; Rapoport, H. J. Org. Chem. 1995, 60, 2683. (b) Davis, C. R.; Johnson, R. A.; Cialdella, J. I.; Liggett, W. F.; Mizsak, S. A.; Marshall, V. P. J. Org. Chem. 1997, 62, 2244. (c) Singh, S.; Basmadjian, G. P. Tetrahedron Lett. 1997, 38, 6829. (d) Ikeda, M.; Kugo, Y.; Kondo, Y.; Yamazaki, T.; Sato, T. J. Chem. Soc., Perkin Trans. 1 1997, 3339. (e) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Tetrahedron 1977, 53, 17177. (f) Clive, D. L. J.; Yeh, V. S. C. Tetrahedron Lett. 1998, 39, 4789.
50. For formal synthesis of epibatidine, see: (a) Hernández, A.; Marcos, M.; Rapoport, H. J. Org. Chem. 1995, 60, 2683. (b) Davis, C. R.; Johnson, R. A.; Cialdella, J. I.; Liggett, W. F.; Mizsak, S. A.; Marshall, V. P. J. Org. Chem. 1997, 62, 2244. (c) Singh, S.; Basmadjian, G. P. Tetrahedron Lett. 1997, 38, 6829. (d) Ikeda, M.; Kugo, Y.; Kondo, Y.; Yamazaki, T.; Sato, T. J. Chem. Soc., Perkin Trans. 1 1997, 3339. (e) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Tetrahedron 1977, 53, 17177. (f) Clive, D. L. J.; Yeh, V. S. C. Tetrahedron Lett. 1998, 39, 4789.
51. For formal synthesis of epibatidine, see: (a) Hernández, A.; Marcos, M.; Rapoport, H. J. Org. Chem. 1995, 60, 2683. (b) Davis, C. R.; Johnson, R. A.; Cialdella, J. I.; Liggett, W. F.; Mizsak, S. A.; Marshall, V. P. J. Org. Chem. 1997, 62, 2244. (c) Singh, S.; Basmadjian, G. P. Tetrahedron Lett. 1997, 38, 6829. (d) Ikeda, M.; Kugo, Y.; Kondo, Y.; Yamazaki, T.; Sato, T. J. Chem. Soc., Perkin Trans. 1 1997, 3339. (e) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Tetrahedron 1977, 53, 17177. (f) Clive, D. L. J.; Yeh, V. S. C. Tetrahedron Lett. 1998, 39, 4789.
52. 1 (19) For a review of our own achievements in natural products synthesis via acylnitroso Diels-Alder methodology, see: Kibayashi, C.; Aoyagi, S. Synlett 1995, 873.
53. For reviews on the application of nitroso Diels-Alder reactions in natural products synthesis, see: (a) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987. (b) Streith, J.; Defoin, A. Synthesis 1994, 1107.
54. For reviews on the application of nitroso Diels-Alder reactions in natural products synthesis, see: (a) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987. (b) Streith, J.; Defoin, A. Synthesis 1994, 1107.
55. For a part of a preliminary account of this work on the synthesis of (-)-epibatidine, see: Aoyagi, S.; Tanaka, R.; Naruse, M.; Kibayashi, C. Teterahedron Lett. 1998, 39, 4513.
56. Sato, M.; Aoyagi, S.; Yago, S.; Kibayashi, C. Tetrahedron Lett. 1996, 37, 9063.
57. Corey, E. J.; Ensley, H. E. J. Am. Chem. Soc. 1975, 97, 6908.
58. Whitesell, J. K. Chem. Rev. 1992, 92, 953.
59. For a review on Π-stacking effects in asymmetric synthesis, see: Jones, G. B.; Chapman, B. J. Synthesis 1995, 475.
60. For examples of hetero Diels-Alder reactions with chiral acylnitroso dienophiles, see: (a) Defoin, A.; Fritz, H.; Schmidlin, C.; Streith, J. Helv. Chim. Acta 1987, 70, 554. (b) Kirby, G. W.; Nazeer, M. Tetrhedron Lett. 1988, 29, 6173; J. Chem. Soc., Perkin Trans, 1 1993, 1397. (c) Millar, A.; Paterson, T. McC.; Procter, G. Synlett 1989, 32. (d) Brouillard-Poichet, A.; Defoin, A.; Streith, J. Tetrahedron Lett. 1989, 30, 7061. Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1992, 75, 109. (e) Gouverneur, V.; Ghosez, L. Tetrahedron: Asymmetry 1990, 1, 363. (f) Gouverneur, V.; Dive, G.; Ghosez, L. Tetrahedron: Asymmetry 1991, 2, 1173. (g) Gouverneur, V.; Ghosez, L. Tetrahedron Lett. 1991, 32, 5349. (h) Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1991, 74, 103. (i) Martin, S. F.; Hartmann, M.; Josey, J. A. Tetrahedron Lett. 1992, 35, 3583-3586. (J) Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. J. N. Tetrahedron: Asymmetry 1994, 5, 1535. (k) Ritter, A. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4602. (l) Shustov, G. V.; Rauk, A. Tetrahedron Lett. 1995, 36, 5449. (m) Lin, C.-C.; Wang, Y.-C.; Hsu, J.-L.; Chiang, C.-C.; Su, D.-W.; Yan, T.-H. J. Org. Chem. 1997, 62, 3806.
61. For examples of hetero Diels-Alder reactions with chiral acylnitroso dienophiles, see: (a) Defoin, A.; Fritz, H.; Schmidlin, C.; Streith, J. Helv. Chim. Acta 1987, 70, 554. (b) Kirby, G. W.; Nazeer, M. Tetrhedron Lett. 1988, 29, 6173; J. Chem. Soc., Perkin Trans, 1 1993, 1397. (c) Millar, A.; Paterson, T. McC.; Procter, G. Synlett 1989, 32. (d) Brouillard-Poichet, A.; Defoin, A.; Streith, J. Tetrahedron Lett. 1989, 30, 7061. Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1992, 75, 109. (e) Gouverneur, V.; Ghosez, L. Tetrahedron: Asymmetry 1990, 1, 363. (f) Gouverneur, V.; Dive, G.; Ghosez, L. Tetrahedron: Asymmetry 1991, 2, 1173. (g) Gouverneur, V.; Ghosez, L. Tetrahedron Lett. 1991, 32, 5349. (h) Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1991, 74, 103. (i) Martin, S. F.; Hartmann, M.; Josey, J. A. Tetrahedron Lett. 1992, 35, 3583-3586. (J) Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. J. N. Tetrahedron: Asymmetry 1994, 5, 1535. (k) Ritter, A. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4602. (l) Shustov, G. V.; Rauk, A. Tetrahedron Lett. 1995, 36, 5449. (m) Lin, C.-C.; Wang, Y.-C.; Hsu, J.-L.; Chiang, C.-C.; Su, D.-W.; Yan, T.-H. J. Org. Chem. 1997, 62, 3806.
62. For examples of hetero Diels-Alder reactions with chiral acylnitroso dienophiles, see: (a) Defoin, A.; Fritz, H.; Schmidlin, C.; Streith, J. Helv. Chim. Acta 1987, 70, 554. (b) Kirby, G. W.; Nazeer, M. Tetrhedron Lett. 1988, 29, 6173; J. Chem. Soc., Perkin Trans, 1 1993, 1397. (c) Millar, A.; Paterson, T. McC.; Procter, G. Synlett 1989, 32. (d) Brouillard-Poichet, A.; Defoin, A.; Streith, J. Tetrahedron Lett. 1989, 30, 7061. Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1992, 75, 109. (e) Gouverneur, V.; Ghosez, L. Tetrahedron: Asymmetry 1990, 1, 363. (f) Gouverneur, V.; Dive, G.; Ghosez, L. Tetrahedron: Asymmetry 1991, 2, 1173. (g) Gouverneur, V.; Ghosez, L. Tetrahedron Lett. 1991, 32, 5349. (h) Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1991, 74, 103. (i) Martin, S. F.; Hartmann, M.; Josey, J. A. Tetrahedron Lett. 1992, 35, 3583-3586. (J) Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. J. N. Tetrahedron: Asymmetry 1994, 5, 1535. (k) Ritter, A. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4602. (l) Shustov, G. V.; Rauk, A. Tetrahedron Lett. 1995, 36, 5449. (m) Lin, C.-C.; Wang, Y.-C.; Hsu, J.-L.; Chiang, C.-C.; Su, D.-W.; Yan, T.-H. J. Org. Chem. 1997, 62, 3806.
63. For examples of hetero Diels-Alder reactions with chiral acylnitroso dienophiles, see: (a) Defoin, A.; Fritz, H.; Schmidlin, C.; Streith, J. Helv. Chim. Acta 1987, 70, 554. (b) Kirby, G. W.; Nazeer, M. Tetrhedron Lett. 1988, 29, 6173; J. Chem. Soc., Perkin Trans, 1 1993, 1397. (c) Millar, A.; Paterson, T. McC.; Procter, G. Synlett 1989, 32. (d) Brouillard-Poichet, A.; Defoin, A.; Streith, J. Tetrahedron Lett. 1989, 30, 7061. Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1992, 75, 109. (e) Gouverneur, V.; Ghosez, L. Tetrahedron: Asymmetry 1990, 1, 363. (f) Gouverneur, V.; Dive, G.; Ghosez, L. Tetrahedron: Asymmetry 1991, 2, 1173. (g) Gouverneur, V.; Ghosez, L. Tetrahedron Lett. 1991, 32, 5349. (h) Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1991, 74, 103. (i) Martin, S. F.; Hartmann, M.; Josey, J. A. Tetrahedron Lett. 1992, 35, 3583-3586. (J) Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. J. N. Tetrahedron: Asymmetry 1994, 5, 1535. (k) Ritter, A. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4602. (l) Shustov, G. V.; Rauk, A. Tetrahedron Lett. 1995, 36, 5449. (m) Lin, C.-C.; Wang, Y.-C.; Hsu, J.-L.; Chiang, C.-C.; Su, D.-W.; Yan, T.-H. J. Org. Chem. 1997, 62, 3806.
64. For examples of hetero Diels-Alder reactions with chiral acylnitroso dienophiles, see: (a) Defoin, A.; Fritz, H.; Schmidlin, C.; Streith, J. Helv. Chim. Acta 1987, 70, 554. (b) Kirby, G. W.; Nazeer, M. Tetrhedron Lett. 1988, 29, 6173; J. Chem. Soc., Perkin Trans, 1 1993, 1397. (c) Millar, A.; Paterson, T. McC.; Procter, G. Synlett 1989, 32. (d) Brouillard-Poichet, A.; Defoin, A.; Streith, J. Tetrahedron Lett. 1989, 30, 7061. Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1992, 75, 109. (e) Gouverneur, V.; Ghosez, L. Tetrahedron: Asymmetry 1990, 1, 363. (f) Gouverneur, V.; Dive, G.; Ghosez, L. Tetrahedron: Asymmetry 1991, 2, 1173. (g) Gouverneur, V.; Ghosez, L. Tetrahedron Lett. 1991, 32, 5349. (h) Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1991, 74, 103. (i) Martin, S. F.; Hartmann, M.; Josey, J. A. Tetrahedron Lett. 1992, 35, 3583-3586. (J) Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. J. N. Tetrahedron: Asymmetry 1994, 5, 1535. (k) Ritter, A. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4602. (l) Shustov, G. V.; Rauk, A. Tetrahedron Lett. 1995, 36, 5449. (m) Lin, C.-C.; Wang, Y.-C.; Hsu, J.-L.; Chiang, C.-C.; Su, D.-W.; Yan, T.-H. J. Org. Chem. 1997, 62, 3806.
65. For examples of hetero Diels-Alder reactions with chiral acylnitroso dienophiles, see: (a) Defoin, A.; Fritz, H.; Schmidlin, C.; Streith, J. Helv. Chim. Acta 1987, 70, 554. (b) Kirby, G. W.; Nazeer, M. Tetrhedron Lett. 1988, 29, 6173; J. Chem. Soc., Perkin Trans, 1 1993, 1397. (c) Millar, A.; Paterson, T. McC.; Procter, G. Synlett 1989, 32. (d) Brouillard-Poichet, A.; Defoin, A.; Streith, J. Tetrahedron Lett. 1989, 30, 7061. Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1992, 75, 109. (e) Gouverneur, V.; Ghosez, L. Tetrahedron: Asymmetry 1990, 1, 363. (f) Gouverneur, V.; Dive, G.; Ghosez, L. Tetrahedron: Asymmetry 1991, 2, 1173. (g) Gouverneur, V.; Ghosez, L. Tetrahedron Lett. 1991, 32, 5349. (h) Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1991, 74, 103. (i) Martin, S. F.; Hartmann, M.; Josey, J. A. Tetrahedron Lett. 1992, 35, 3583-3586. (J) Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. J. N. Tetrahedron: Asymmetry 1994, 5, 1535. (k) Ritter, A. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4602. (l) Shustov, G. V.; Rauk, A. Tetrahedron Lett. 1995, 36, 5449. (m) Lin, C.-C.; Wang, Y.-C.; Hsu, J.-L.; Chiang, C.-C.; Su, D.-W.; Yan, T.-H. J. Org. Chem. 1997, 62, 3806.
66. For examples of hetero Diels-Alder reactions with chiral acylnitroso dienophiles, see: (a) Defoin, A.; Fritz, H.; Schmidlin, C.; Streith, J. Helv. Chim. Acta 1987, 70, 554. (b) Kirby, G. W.; Nazeer, M. Tetrhedron Lett. 1988, 29, 6173; J. Chem. Soc., Perkin Trans, 1 1993, 1397. (c) Millar, A.; Paterson, T. McC.; Procter, G. Synlett 1989, 32. (d) Brouillard-Poichet, A.; Defoin, A.; Streith, J. Tetrahedron Lett. 1989, 30, 7061. Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1992, 75, 109. (e) Gouverneur, V.; Ghosez, L. Tetrahedron: Asymmetry 1990, 1, 363. (f) Gouverneur, V.; Dive, G.; Ghosez, L. Tetrahedron: Asymmetry 1991, 2, 1173. (g) Gouverneur, V.; Ghosez, L. Tetrahedron Lett. 1991, 32, 5349. (h) Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1991, 74, 103. (i) Martin, S. F.; Hartmann, M.; Josey, J. A. Tetrahedron Lett. 1992, 35, 3583-3586. (J) Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. J. N. Tetrahedron: Asymmetry 1994, 5, 1535. (k) Ritter, A. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4602. (l) Shustov, G. V.; Rauk, A. Tetrahedron Lett. 1995, 36, 5449. (m) Lin, C.-C.; Wang, Y.-C.; Hsu, J.-L.; Chiang, C.-C.; Su, D.-W.; Yan, T.-H. J. Org. Chem. 1997, 62, 3806.
67. For examples of hetero Diels-Alder reactions with chiral acylnitroso dienophiles, see: (a) Defoin, A.; Fritz, H.; Schmidlin, C.; Streith, J. Helv. Chim. Acta 1987, 70, 554. (b) Kirby, G. W.; Nazeer, M. Tetrhedron Lett. 1988, 29, 6173; J. Chem. Soc., Perkin Trans, 1 1993, 1397. (c) Millar, A.; Paterson, T. McC.; Procter, G. Synlett 1989, 32. (d) Brouillard-Poichet, A.; Defoin, A.; Streith, J. Tetrahedron Lett. 1989, 30, 7061. Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1992, 75, 109. (e) Gouverneur, V.; Ghosez, L. Tetrahedron: Asymmetry 1990, 1, 363. (f) Gouverneur, V.; Dive, G.; Ghosez, L. Tetrahedron: Asymmetry 1991, 2, 1173. (g) Gouverneur, V.; Ghosez, L. Tetrahedron Lett. 1991, 32, 5349. (h) Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1991, 74, 103. (i) Martin, S. F.; Hartmann, M.; Josey, J. A. Tetrahedron Lett. 1992, 35, 3583-3586. (J) Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. J. N. Tetrahedron: Asymmetry 1994, 5, 1535. (k) Ritter, A. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4602. (l) Shustov, G. V.; Rauk, A. Tetrahedron Lett. 1995, 36, 5449. (m) Lin, C.-C.; Wang, Y.-C.; Hsu, J.-L.; Chiang, C.-C.; Su, D.-W.; Yan, T.-H. J. Org. Chem. 1997, 62, 3806.
68. For examples of hetero Diels-Alder reactions with chiral acylnitroso dienophiles, see: (a) Defoin, A.; Fritz, H.; Schmidlin, C.; Streith, J. Helv. Chim. Acta 1987, 70, 554. (b) Kirby, G. W.; Nazeer, M. Tetrhedron Lett. 1988, 29, 6173; J. Chem. Soc., Perkin Trans, 1 1993, 1397. (c) Millar, A.; Paterson, T. McC.; Procter, G. Synlett 1989, 32. (d) Brouillard-Poichet, A.; Defoin, A.; Streith, J. Tetrahedron Lett. 1989, 30, 7061. Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1992, 75, 109. (e) Gouverneur, V.; Ghosez, L. Tetrahedron: Asymmetry 1990, 1, 363. (f) Gouverneur, V.; Dive, G.; Ghosez, L. Tetrahedron: Asymmetry 1991, 2, 1173. (g) Gouverneur, V.; Ghosez, L. Tetrahedron Lett. 1991, 32, 5349. (h) Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1991, 74, 103. (i) Martin, S. F.; Hartmann, M.; Josey, J. A. Tetrahedron Lett. 1992, 35, 3583-3586. (J) Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. J. N. Tetrahedron: Asymmetry 1994, 5, 1535. (k) Ritter, A. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4602. (l) Shustov, G. V.; Rauk, A. Tetrahedron Lett. 1995, 36, 5449. (m) Lin, C.-C.; Wang, Y.-C.; Hsu, J.-L.; Chiang, C.-C.; Su, D.-W.; Yan, T.-H. J. Org. Chem. 1997, 62, 3806.
69. For examples of hetero Diels-Alder reactions with chiral acylnitroso dienophiles, see: (a) Defoin, A.; Fritz, H.; Schmidlin, C.; Streith, J. Helv. Chim. Acta 1987, 70, 554. (b) Kirby, G. W.; Nazeer, M. Tetrhedron Lett. 1988, 29, 6173; J. Chem. Soc., Perkin Trans, 1 1993, 1397. (c) Millar, A.; Paterson, T. McC.; Procter, G. Synlett 1989, 32. (d) Brouillard-Poichet, A.; Defoin, A.; Streith, J. Tetrahedron Lett. 1989, 30, 7061. Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1992, 75, 109. (e) Gouverneur, V.; Ghosez, L. Tetrahedron: Asymmetry 1990, 1, 363. (f) Gouverneur, V.; Dive, G.; Ghosez, L. Tetrahedron: Asymmetry 1991, 2, 1173. (g) Gouverneur, V.; Ghosez, L. Tetrahedron Lett. 1991, 32, 5349. (h) Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1991, 74, 103. (i) Martin, S. F.; Hartmann, M.; Josey, J. A. Tetrahedron Lett. 1992, 35, 3583-3586. (J) Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. J. N. Tetrahedron: Asymmetry 1994, 5, 1535. (k) Ritter, A. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4602. (l) Shustov, G. V.; Rauk, A. Tetrahedron Lett. 1995, 36, 5449. (m) Lin, C.-C.; Wang, Y.-C.; Hsu, J.-L.; Chiang, C.-C.; Su, D.-W.; Yan, T.-H. J. Org. Chem. 1997, 62, 3806.
70. For examples of hetero Diels-Alder reactions with chiral acylnitroso dienophiles, see: (a) Defoin, A.; Fritz, H.; Schmidlin, C.; Streith, J. Helv. Chim. Acta 1987, 70, 554. (b) Kirby, G. W.; Nazeer, M. Tetrhedron Lett. 1988, 29, 6173; J. Chem. Soc., Perkin Trans, 1 1993, 1397. (c) Millar, A.; Paterson, T. McC.; Procter, G. Synlett 1989, 32. (d) Brouillard-Poichet, A.; Defoin, A.; Streith, J. Tetrahedron Lett. 1989, 30, 7061. Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1992, 75, 109. (e) Gouverneur, V.; Ghosez, L. Tetrahedron: Asymmetry 1990, 1, 363. (f) Gouverneur, V.; Dive, G.; Ghosez, L. Tetrahedron: Asymmetry 1991, 2, 1173. (g) Gouverneur, V.; Ghosez, L. Tetrahedron Lett. 1991, 32, 5349. (h) Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1991, 74, 103. (i) Martin, S. F.; Hartmann, M.; Josey, J. A. Tetrahedron Lett. 1992, 35, 3583-3586. (J) Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. J. N. Tetrahedron: Asymmetry 1994, 5, 1535. (k) Ritter, A. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4602. (l) Shustov, G. V.; Rauk, A. Tetrahedron Lett. 1995, 36, 5449. (m) Lin, C.-C.; Wang, Y.-C.; Hsu, J.-L.; Chiang, C.-C.; Su, D.-W.; Yan, T.-H. J. Org. Chem. 1997, 62, 3806.
71. For examples of hetero Diels-Alder reactions with chiral acylnitroso dienophiles, see: (a) Defoin, A.; Fritz, H.; Schmidlin, C.; Streith, J. Helv. Chim. Acta 1987, 70, 554. (b) Kirby, G. W.; Nazeer, M. Tetrhedron Lett. 1988, 29, 6173; J. Chem. Soc., Perkin Trans, 1 1993, 1397. (c) Millar, A.; Paterson, T. McC.; Procter, G. Synlett 1989, 32. (d) Brouillard-Poichet, A.; Defoin, A.; Streith, J. Tetrahedron Lett. 1989, 30, 7061. Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1992, 75, 109. (e) Gouverneur, V.; Ghosez, L. Tetrahedron: Asymmetry 1990, 1, 363. (f) Gouverneur, V.; Dive, G.; Ghosez, L. Tetrahedron: Asymmetry 1991, 2, 1173. (g) Gouverneur, V.; Ghosez, L. Tetrahedron Lett. 1991, 32, 5349. (h) Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1991, 74, 103. (i) Martin, S. F.; Hartmann, M.; Josey, J. A. Tetrahedron Lett. 1992, 35, 3583-3586. (J) Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. J. N. Tetrahedron: Asymmetry 1994, 5, 1535. (k) Ritter, A. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4602. (l) Shustov, G. V.; Rauk, A. Tetrahedron Lett. 1995, 36, 5449. (m) Lin, C.-C.; Wang, Y.-C.; Hsu, J.-L.; Chiang, C.-C.; Su, D.-W.; Yan, T.-H. J. Org. Chem. 1997, 62, 3806.
72. For examples of hetero Diels-Alder reactions with chiral acylnitroso dienophiles, see: (a) Defoin, A.; Fritz, H.; Schmidlin, C.; Streith, J. Helv. Chim. Acta 1987, 70, 554. (b) Kirby, G. W.; Nazeer, M. Tetrhedron Lett. 1988, 29, 6173; J. Chem. Soc., Perkin Trans, 1 1993, 1397. (c) Millar, A.; Paterson, T. McC.; Procter, G. Synlett 1989, 32. (d) Brouillard-Poichet, A.; Defoin, A.; Streith, J. Tetrahedron Lett. 1989, 30, 7061. Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1992, 75, 109. (e) Gouverneur, V.; Ghosez, L. Tetrahedron: Asymmetry 1990, 1, 363. (f) Gouverneur, V.; Dive, G.; Ghosez, L. Tetrahedron: Asymmetry 1991, 2, 1173. (g) Gouverneur, V.; Ghosez, L. Tetrahedron Lett. 1991, 32, 5349. (h) Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1991, 74, 103. (i) Martin, S. F.; Hartmann, M.; Josey, J. A. Tetrahedron Lett. 1992, 35, 3583-3586. (J) Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. J. N. Tetrahedron: Asymmetry 1994, 5, 1535. (k) Ritter, A. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4602. (l) Shustov, G. V.; Rauk, A. Tetrahedron Lett. 1995, 36, 5449. (m) Lin, C.-C.; Wang, Y.-C.; Hsu, J.-L.; Chiang, C.-C.; Su, D.-W.; Yan, T.-H. J. Org. Chem. 1997, 62, 3806.
73. For examples of hetero Diels-Alder reactions with chiral acylnitroso dienophiles, see: (a) Defoin, A.; Fritz, H.; Schmidlin, C.; Streith, J. Helv. Chim. Acta 1987, 70, 554. (b) Kirby, G. W.; Nazeer, M. Tetrhedron Lett. 1988, 29, 6173; J. Chem. Soc., Perkin Trans, 1 1993, 1397. (c) Millar, A.; Paterson, T. McC.; Procter, G. Synlett 1989, 32. (d) Brouillard-Poichet, A.; Defoin, A.; Streith, J. Tetrahedron Lett. 1989, 30, 7061. Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1992, 75, 109. (e) Gouverneur, V.; Ghosez, L. Tetrahedron: Asymmetry 1990, 1, 363. (f) Gouverneur, V.; Dive, G.; Ghosez, L. Tetrahedron: Asymmetry 1991, 2, 1173. (g) Gouverneur, V.; Ghosez, L. Tetrahedron Lett. 1991, 32, 5349. (h) Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1991, 74, 103. (i) Martin, S. F.; Hartmann, M.; Josey, J. A. Tetrahedron Lett. 1992, 35, 3583-3586. (J) Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. J. N. Tetrahedron: Asymmetry 1994, 5, 1535. (k) Ritter, A. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4602. (l) Shustov, G. V.; Rauk, A. Tetrahedron Lett. 1995, 36, 5449. (m) Lin, C.-C.; Wang, Y.-C.; Hsu, J.-L.; Chiang, C.-C.; Su, D.-W.; Yan, T.-H. J. Org. Chem. 1997, 62, 3806.
74. For examples of hetero Diels-Alder reactions with chiral acylnitroso dienophiles, see: (a) Defoin, A.; Fritz, H.; Schmidlin, C.; Streith, J. Helv. Chim. Acta 1987, 70, 554. (b) Kirby, G. W.; Nazeer, M. Tetrhedron Lett. 1988, 29, 6173; J. Chem. Soc., Perkin Trans, 1 1993, 1397. (c) Millar, A.; Paterson, T. McC.; Procter, G. Synlett 1989, 32. (d) Brouillard-Poichet, A.; Defoin, A.; Streith, J. Tetrahedron Lett. 1989, 30, 7061. Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1992, 75, 109. (e) Gouverneur, V.; Ghosez, L. Tetrahedron: Asymmetry 1990, 1, 363. (f) Gouverneur, V.; Dive, G.; Ghosez, L. Tetrahedron: Asymmetry 1991, 2, 1173. (g) Gouverneur, V.; Ghosez, L. Tetrahedron Lett. 1991, 32, 5349. (h) Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1991, 74, 103. (i) Martin, S. F.; Hartmann, M.; Josey, J. A. Tetrahedron Lett. 1992, 35, 3583-3586. (J) Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. J. N. Tetrahedron: Asymmetry 1994, 5, 1535. (k) Ritter, A. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4602. (l) Shustov, G. V.; Rauk, A. Tetrahedron Lett. 1995, 36, 5449. (m) Lin, C.-C.; Wang, Y.-C.; Hsu, J.-L.; Chiang, C.-C.; Su, D.-W.; Yan, T.-H. J. Org. Chem. 1997, 62, 3806.
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88. The efficiency of the menthol chiral auxiliary bearing a naphthalene nucleus has been demonstrated. (a) Mezrhab, B.; Dumas, F.; d'Angelo, J.; Riche, C. J. Org. Chem. 1994, 59, 500. (b) Dumas, F.; Mezrhab, B.; d'Angelo, J. J. Org. Chem. 1996, 61, 2293. See also ref 22.
89. The efficiency of the menthol chiral auxiliary bearing a naphthalene nucleus has been demonstrated. (a) Mezrhab, B.; Dumas, F.; d'Angelo, J.; Riche, C. J. Org. Chem. 1994, 59, 500. (b) Dumas, F.; Mezrhab, B.; d'Angelo, J. J. Org. Chem. 1996, 61, 2293. See also ref 22.
90. A sample of (S)-(-)-pulegone was kindly provided by Takasago International Co.
91. In this cycloaddition, the use of ent-12e is expected to lead to a better selectivity for the desired (1S,4R)-meta-aza isomer, since, as can be seen from the results summarized in Table 1, 12e gives the best diastereoselectivity in the cycloaddition with 1,3-cyclohexadiene. Work in this area is underway in our laboratory.
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