A highly stereoselective asymmetric synthesis of (-)-lobeline and (-)-sedamine

Journal of Organic Chemistry

Volumn 67, Issue 26, 2002, Pages 9192-9199

  Felpin, François Xavier ^a   Lebreton, Jacques ^a  

^a Centre National de la Recherche Scientifique   (France)

Author keywords

[No Author keywords available]

Indexed keywords

DIASTREOMERIC;

ALDEHYDES; CATALYST SELECTIVITY;

SYNTHESIS (CHEMICAL);

3,4 EPOXYALCOHOL; ALKALOID; BENZALDEHYDE; LOBELINE; SEDAMINE; UNCLASSIFIED DRUG;

ARTICLE; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY;

ALKALOIDS; CATALYSIS; CHEMISTRY, ORGANIC; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; LOBELIA; LOBELINE; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PIPERIDINES; PLANTS, MEDICINAL; STEREOISOMERISM;

EID: 0037184884     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020501y     Document Type: Article

References (91)

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13. For racemic syntheses ofsedamine, see: (a) Tufariello, J. J.; Ali, S. A. Tetrahedron Lett. 1978, 47, 4647-4650 (b) Shono T.; Matsumura Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176. (c) Hootelé, C.; Ibebeke-Bomangwa, W.; Driessens, F.; Sabil, S. Bull. Soc. Chim. Belg. 1987, 96, 57-61. (d) Tirel, P. J.; Vaultier, M.; Carrie, R. Tetrahedron Lett. 1989, 30, 1947-1950. (e) Driessens, F.; Hootelé, C. Can. J. Chem. 1991, 69, 211-217. (f) Ozawa, N.; Nakajima, S.; Zaoya, K.; Hamaguchi, F.; Nagasaka, T. Heterocycles 1991, 32, 889-894. (g) Pilli, R. A.; Dias, L. C. Synth. Commun. 1991, 21 2213-2229 (h) Ghiaci, M.; Adibi, M. Org. Prep. Proced. Int. 1996, 28, 474-477. For asymmetric synthesis see: (i) Beyerman, H. C.; Eveleens, W.; Muller, Y. M. F. Recl. Trav. Chim. Pays-Bas 1956, 75, 63-75. (j) Beyerman, H. C.; Eenshuistra, J.; Eveleens, W.; Zweistra, A. Recl. Trav. Chim. Pays-Bas 1959, 78, 43-58. (k) Schöpf, C.; Dummer, G.; Wüst, W. Liebigs Ann. Chem. 1959, 626, 134-1149. (l) Wakabayashi, T.; Watanabe, K.; Kato, Y.; Saito, M. Chem. Lett. 1977, 223-228. (m) Irie, K.; Aoe, K.; Tanaka, T.; Saito, S. J. Chem. Soc., Chem. Commun. 1985, 633-635. (n) Wanner, K. T.; Kärtner, A. Heterocycles 1987, 26, 921-924. (o) Wanner, K. T.; Kärtner, A. Arch. Pharm. 1987, 320, 1253-1267. (p) Pyne, S. G.; Bloem, P.; Chapman, S. L.; Dixon, C. E.; Griffith, R. J. Org. Chem. 1990, 55, 1086-1093. (q) Kiguchi, T.; Nakazono, Y.; Kotera, S.; Ninomiya, I.; Naito, T. Heterocycles 1990, 31, 1525-1535. (r) Comins, D. L.; Hong, H. J. Org. Chem. 1993, 58, 5035-5036. (s) Poerwono, H.; Higashiyama, K.; Takahashi, H. Heterocycles 1998, 47, 263-270. (t) Yu, C.-Y.; Meth-Cohn, O. Tetrahedron Lett. 1999, 40, 6665-6668. (u) Meth-Cohn, O.; Yau, C. C.; Yu, C.-Y. J. Heterocycl. Chem. 1999, 36, 1549-1553. (v) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. Synlett 2000, 1461-1463. (w) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. J. Org. Chem. 2002, 67, 1982-1992.
14. For racemic syntheses ofsedamine, see: (a) Tufariello, J. J.; Ali, S. A. Tetrahedron Lett. 1978, 47, 4647-4650 (b) Shono T.; Matsumura Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176. (c) Hootelé, C.; Ibebeke-Bomangwa, W.; Driessens, F.; Sabil, S. Bull. Soc. Chim. Belg. 1987, 96, 57-61. (d) Tirel, P. J.; Vaultier, M.; Carrie, R. Tetrahedron Lett. 1989, 30, 1947-1950. (e) Driessens, F.; Hootelé, C. Can. J. Chem. 1991, 69, 211-217. (f) Ozawa, N.; Nakajima, S.; Zaoya, K.; Hamaguchi, F.; Nagasaka, T. Heterocycles 1991, 32, 889-894. (g) Pilli, R. A.; Dias, L. C. Synth. Commun. 1991, 21 2213-2229 (h) Ghiaci, M.; Adibi, M. Org. Prep. Proced. Int. 1996, 28, 474-477. For asymmetric synthesis see: (i) Beyerman, H. C.; Eveleens, W.; Muller, Y. M. F. Recl. Trav. Chim. Pays-Bas 1956, 75, 63-75. (j) Beyerman, H. C.; Eenshuistra, J.; Eveleens, W.; Zweistra, A. Recl. Trav. Chim. Pays-Bas 1959, 78, 43-58. (k) Schöpf, C.; Dummer, G.; Wüst, W. Liebigs Ann. Chem. 1959, 626, 134-1149. (l) Wakabayashi, T.; Watanabe, K.; Kato, Y.; Saito, M. Chem. Lett. 1977, 223-228. (m) Irie, K.; Aoe, K.; Tanaka, T.; Saito, S. J. Chem. Soc., Chem. Commun. 1985, 633-635. (n) Wanner, K. T.; Kärtner, A. Heterocycles 1987, 26, 921-924. (o) Wanner, K. T.; Kärtner, A. Arch. Pharm. 1987, 320, 1253-1267. (p) Pyne, S. G.; Bloem, P.; Chapman, S. L.; Dixon, C. E.; Griffith, R. J. Org. Chem. 1990, 55, 1086-1093. (q) Kiguchi, T.; Nakazono, Y.; Kotera, S.; Ninomiya, I.; Naito, T. Heterocycles 1990, 31, 1525-1535. (r) Comins, D. L.; Hong, H. J. Org. Chem. 1993, 58, 5035-5036. (s) Poerwono, H.; Higashiyama, K.; Takahashi, H. Heterocycles 1998, 47, 263-270. (t) Yu, C.-Y.; Meth-Cohn, O. Tetrahedron Lett. 1999, 40, 6665-6668. (u) Meth-Cohn, O.; Yau, C. C.; Yu, C.-Y. J. Heterocycl. Chem. 1999, 36, 1549-1553. (v) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. Synlett 2000, 1461-1463. (w) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. J. Org. Chem. 2002, 67, 1982-1992.
15. For racemic syntheses ofsedamine, see: (a) Tufariello, J. J.; Ali, S. A. Tetrahedron Lett. 1978, 47, 4647-4650 (b) Shono T.; Matsumura Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176. (c) Hootelé, C.; Ibebeke-Bomangwa, W.; Driessens, F.; Sabil, S. Bull. Soc. Chim. Belg. 1987, 96, 57-61. (d) Tirel, P. J.; Vaultier, M.; Carrie, R. Tetrahedron Lett. 1989, 30, 1947-1950. (e) Driessens, F.; Hootelé, C. Can. J. Chem. 1991, 69, 211-217. (f) Ozawa, N.; Nakajima, S.; Zaoya, K.; Hamaguchi, F.; Nagasaka, T. Heterocycles 1991, 32, 889-894. (g) Pilli, R. A.; Dias, L. C. Synth. Commun. 1991, 21 2213-2229 (h) Ghiaci, M.; Adibi, M. Org. Prep. Proced. Int. 1996, 28, 474-477. For asymmetric synthesis see: (i) Beyerman, H. C.; Eveleens, W.; Muller, Y. M. F. Recl. Trav. Chim. Pays-Bas 1956, 75, 63-75. (j) Beyerman, H. C.; Eenshuistra, J.; Eveleens, W.; Zweistra, A. Recl. Trav. Chim. Pays-Bas 1959, 78, 43-58. (k) Schöpf, C.; Dummer, G.; Wüst, W. Liebigs Ann. Chem. 1959, 626, 134-1149. (l) Wakabayashi, T.; Watanabe, K.; Kato, Y.; Saito, M. Chem. Lett. 1977, 223-228. (m) Irie, K.; Aoe, K.; Tanaka, T.; Saito, S. J. Chem. Soc., Chem. Commun. 1985, 633-635. (n) Wanner, K. T.; Kärtner, A. Heterocycles 1987, 26, 921-924. (o) Wanner, K. T.; Kärtner, A. Arch. Pharm. 1987, 320, 1253-1267. (p) Pyne, S. G.; Bloem, P.; Chapman, S. L.; Dixon, C. E.; Griffith, R. J. Org. Chem. 1990, 55, 1086-1093. (q) Kiguchi, T.; Nakazono, Y.; Kotera, S.; Ninomiya, I.; Naito, T. Heterocycles 1990, 31, 1525-1535. (r) Comins, D. L.; Hong, H. J. Org. Chem. 1993, 58, 5035-5036. (s) Poerwono, H.; Higashiyama, K.; Takahashi, H. Heterocycles 1998, 47, 263-270. (t) Yu, C.-Y.; Meth-Cohn, O. Tetrahedron Lett. 1999, 40, 6665-6668. (u) Meth-Cohn, O.; Yau, C. C.; Yu, C.-Y. J. Heterocycl. Chem. 1999, 36, 1549-1553. (v) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. Synlett 2000, 1461-1463. (w) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. J. Org. Chem. 2002, 67, 1982-1992.
16. For racemic syntheses ofsedamine, see: (a) Tufariello, J. J.; Ali, S. A. Tetrahedron Lett. 1978, 47, 4647-4650 (b) Shono T.; Matsumura Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176. (c) Hootelé, C.; Ibebeke-Bomangwa, W.; Driessens, F.; Sabil, S. Bull. Soc. Chim. Belg. 1987, 96, 57-61. (d) Tirel, P. J.; Vaultier, M.; Carrie, R. Tetrahedron Lett. 1989, 30, 1947-1950. (e) Driessens, F.; Hootelé, C. Can. J. Chem. 1991, 69, 211-217. (f) Ozawa, N.; Nakajima, S.; Zaoya, K.; Hamaguchi, F.; Nagasaka, T. Heterocycles 1991, 32, 889-894. (g) Pilli, R. A.; Dias, L. C. Synth. Commun. 1991, 21 2213-2229 (h) Ghiaci, M.; Adibi, M. Org. Prep. Proced. Int. 1996, 28, 474-477. For asymmetric synthesis see: (i) Beyerman, H. C.; Eveleens, W.; Muller, Y. M. F. Recl. Trav. Chim. Pays-Bas 1956, 75, 63-75. (j) Beyerman, H. C.; Eenshuistra, J.; Eveleens, W.; Zweistra, A. Recl. Trav. Chim. Pays-Bas 1959, 78, 43-58. (k) Schöpf, C.; Dummer, G.; Wüst, W. Liebigs Ann. Chem. 1959, 626, 134-1149. (l) Wakabayashi, T.; Watanabe, K.; Kato, Y.; Saito, M. Chem. Lett. 1977, 223-228. (m) Irie, K.; Aoe, K.; Tanaka, T.; Saito, S. J. Chem. Soc., Chem. Commun. 1985, 633-635. (n) Wanner, K. T.; Kärtner, A. Heterocycles 1987, 26, 921-924. (o) Wanner, K. T.; Kärtner, A. Arch. Pharm. 1987, 320, 1253-1267. (p) Pyne, S. G.; Bloem, P.; Chapman, S. L.; Dixon, C. E.; Griffith, R. J. Org. Chem. 1990, 55, 1086-1093. (q) Kiguchi, T.; Nakazono, Y.; Kotera, S.; Ninomiya, I.; Naito, T. Heterocycles 1990, 31, 1525-1535. (r) Comins, D. L.; Hong, H. J. Org. Chem. 1993, 58, 5035-5036. (s) Poerwono, H.; Higashiyama, K.; Takahashi, H. Heterocycles 1998, 47, 263-270. (t) Yu, C.-Y.; Meth-Cohn, O. Tetrahedron Lett. 1999, 40, 6665-6668. (u) Meth-Cohn, O.; Yau, C. C.; Yu, C.-Y. J. Heterocycl. Chem. 1999, 36, 1549-1553. (v) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. Synlett 2000, 1461-1463. (w) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. J. Org. Chem. 2002, 67, 1982-1992.
17. For racemic syntheses ofsedamine, see: (a) Tufariello, J. J.; Ali, S. A. Tetrahedron Lett. 1978, 47, 4647-4650 (b) Shono T.; Matsumura Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176. (c) Hootelé, C.; Ibebeke-Bomangwa, W.; Driessens, F.; Sabil, S. Bull. Soc. Chim. Belg. 1987, 96, 57-61. (d) Tirel, P. J.; Vaultier, M.; Carrie, R. Tetrahedron Lett. 1989, 30, 1947-1950. (e) Driessens, F.; Hootelé, C. Can. J. Chem. 1991, 69, 211-217. (f) Ozawa, N.; Nakajima, S.; Zaoya, K.; Hamaguchi, F.; Nagasaka, T. Heterocycles 1991, 32, 889-894. (g) Pilli, R. A.; Dias, L. C. Synth. Commun. 1991, 21 2213-2229 (h) Ghiaci, M.; Adibi, M. Org. Prep. Proced. Int. 1996, 28, 474-477. For asymmetric synthesis see: (i) Beyerman, H. C.; Eveleens, W.; Muller, Y. M. F. Recl. Trav. Chim. Pays-Bas 1956, 75, 63-75. (j) Beyerman, H. C.; Eenshuistra, J.; Eveleens, W.; Zweistra, A. Recl. Trav. Chim. Pays-Bas 1959, 78, 43-58. (k) Schöpf, C.; Dummer, G.; Wüst, W. Liebigs Ann. Chem. 1959, 626, 134-1149. (l) Wakabayashi, T.; Watanabe, K.; Kato, Y.; Saito, M. Chem. Lett. 1977, 223-228. (m) Irie, K.; Aoe, K.; Tanaka, T.; Saito, S. J. Chem. Soc., Chem. Commun. 1985, 633-635. (n) Wanner, K. T.; Kärtner, A. Heterocycles 1987, 26, 921-924. (o) Wanner, K. T.; Kärtner, A. Arch. Pharm. 1987, 320, 1253-1267. (p) Pyne, S. G.; Bloem, P.; Chapman, S. L.; Dixon, C. E.; Griffith, R. J. Org. Chem. 1990, 55, 1086-1093. (q) Kiguchi, T.; Nakazono, Y.; Kotera, S.; Ninomiya, I.; Naito, T. Heterocycles 1990, 31, 1525-1535. (r) Comins, D. L.; Hong, H. J. Org. Chem. 1993, 58, 5035-5036. (s) Poerwono, H.; Higashiyama, K.; Takahashi, H. Heterocycles 1998, 47, 263-270. (t) Yu, C.-Y.; Meth-Cohn, O. Tetrahedron Lett. 1999, 40, 6665-6668. (u) Meth-Cohn, O.; Yau, C. C.; Yu, C.-Y. J. Heterocycl. Chem. 1999, 36, 1549-1553. (v) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. Synlett 2000, 1461-1463. (w) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. J. Org. Chem. 2002, 67, 1982-1992.
18. For racemic syntheses ofsedamine, see: (a) Tufariello, J. J.; Ali, S. A. Tetrahedron Lett. 1978, 47, 4647-4650 (b) Shono T.; Matsumura Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176. (c) Hootelé, C.; Ibebeke-Bomangwa, W.; Driessens, F.; Sabil, S. Bull. Soc. Chim. Belg. 1987, 96, 57-61. (d) Tirel, P. J.; Vaultier, M.; Carrie, R. Tetrahedron Lett. 1989, 30, 1947-1950. (e) Driessens, F.; Hootelé, C. Can. J. Chem. 1991, 69, 211-217. (f) Ozawa, N.; Nakajima, S.; Zaoya, K.; Hamaguchi, F.; Nagasaka, T. Heterocycles 1991, 32, 889-894. (g) Pilli, R. A.; Dias, L. C. Synth. Commun. 1991, 21 2213-2229 (h) Ghiaci, M.; Adibi, M. Org. Prep. Proced. Int. 1996, 28, 474-477. For asymmetric synthesis see: (i) Beyerman, H. C.; Eveleens, W.; Muller, Y. M. F. Recl. Trav. Chim. Pays-Bas 1956, 75, 63-75. (j) Beyerman, H. C.; Eenshuistra, J.; Eveleens, W.; Zweistra, A. Recl. Trav. Chim. Pays-Bas 1959, 78, 43-58. (k) Schöpf, C.; Dummer, G.; Wüst, W. Liebigs Ann. Chem. 1959, 626, 134-1149. (l) Wakabayashi, T.; Watanabe, K.; Kato, Y.; Saito, M. Chem. Lett. 1977, 223-228. (m) Irie, K.; Aoe, K.; Tanaka, T.; Saito, S. J. Chem. Soc., Chem. Commun. 1985, 633-635. (n) Wanner, K. T.; Kärtner, A. Heterocycles 1987, 26, 921-924. (o) Wanner, K. T.; Kärtner, A. Arch. Pharm. 1987, 320, 1253-1267. (p) Pyne, S. G.; Bloem, P.; Chapman, S. L.; Dixon, C. E.; Griffith, R. J. Org. Chem. 1990, 55, 1086-1093. (q) Kiguchi, T.; Nakazono, Y.; Kotera, S.; Ninomiya, I.; Naito, T. Heterocycles 1990, 31, 1525-1535. (r) Comins, D. L.; Hong, H. J. Org. Chem. 1993, 58, 5035-5036. (s) Poerwono, H.; Higashiyama, K.; Takahashi, H. Heterocycles 1998, 47, 263-270. (t) Yu, C.-Y.; Meth-Cohn, O. Tetrahedron Lett. 1999, 40, 6665-6668. (u) Meth-Cohn, O.; Yau, C. C.; Yu, C.-Y. J. Heterocycl. Chem. 1999, 36, 1549-1553. (v) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. Synlett 2000, 1461-1463. (w) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. J. Org. Chem. 2002, 67, 1982-1992.
19. For racemic syntheses ofsedamine, see: (a) Tufariello, J. J.; Ali, S. A. Tetrahedron Lett. 1978, 47, 4647-4650 (b) Shono T.; Matsumura Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176. (c) Hootelé, C.; Ibebeke-Bomangwa, W.; Driessens, F.; Sabil, S. Bull. Soc. Chim. Belg. 1987, 96, 57-61. (d) Tirel, P. J.; Vaultier, M.; Carrie, R. Tetrahedron Lett. 1989, 30, 1947-1950. (e) Driessens, F.; Hootelé, C. Can. J. Chem. 1991, 69, 211-217. (f) Ozawa, N.; Nakajima, S.; Zaoya, K.; Hamaguchi, F.; Nagasaka, T. Heterocycles 1991, 32, 889-894. (g) Pilli, R. A.; Dias, L. C. Synth. Commun. 1991, 21 2213-2229 (h) Ghiaci, M.; Adibi, M. Org. Prep. Proced. Int. 1996, 28, 474-477. For asymmetric synthesis see: (i) Beyerman, H. C.; Eveleens, W.; Muller, Y. M. F. Recl. Trav. Chim. Pays-Bas 1956, 75, 63-75. (j) Beyerman, H. C.; Eenshuistra, J.; Eveleens, W.; Zweistra, A. Recl. Trav. Chim. Pays-Bas 1959, 78, 43-58. (k) Schöpf, C.; Dummer, G.; Wüst, W. Liebigs Ann. Chem. 1959, 626, 134-1149. (l) Wakabayashi, T.; Watanabe, K.; Kato, Y.; Saito, M. Chem. Lett. 1977, 223-228. (m) Irie, K.; Aoe, K.; Tanaka, T.; Saito, S. J. Chem. Soc., Chem. Commun. 1985, 633-635. (n) Wanner, K. T.; Kärtner, A. Heterocycles 1987, 26, 921-924. (o) Wanner, K. T.; Kärtner, A. Arch. Pharm. 1987, 320, 1253-1267. (p) Pyne, S. G.; Bloem, P.; Chapman, S. L.; Dixon, C. E.; Griffith, R. J. Org. Chem. 1990, 55, 1086-1093. (q) Kiguchi, T.; Nakazono, Y.; Kotera, S.; Ninomiya, I.; Naito, T. Heterocycles 1990, 31, 1525-1535. (r) Comins, D. L.; Hong, H. J. Org. Chem. 1993, 58, 5035-5036. (s) Poerwono, H.; Higashiyama, K.; Takahashi, H. Heterocycles 1998, 47, 263-270. (t) Yu, C.-Y.; Meth-Cohn, O. Tetrahedron Lett. 1999, 40, 6665-6668. (u) Meth-Cohn, O.; Yau, C. C.; Yu, C.-Y. J. Heterocycl. Chem. 1999, 36, 1549-1553. (v) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. Synlett 2000, 1461-1463. (w) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. J. Org. Chem. 2002, 67, 1982-1992.
20. For racemic syntheses ofsedamine, see: (a) Tufariello, J. J.; Ali, S. A. Tetrahedron Lett. 1978, 47, 4647-4650 (b) Shono T.; Matsumura Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176. (c) Hootelé, C.; Ibebeke-Bomangwa, W.; Driessens, F.; Sabil, S. Bull. Soc. Chim. Belg. 1987, 96, 57-61. (d) Tirel, P. J.; Vaultier, M.; Carrie, R. Tetrahedron Lett. 1989, 30, 1947-1950. (e) Driessens, F.; Hootelé, C. Can. J. Chem. 1991, 69, 211-217. (f) Ozawa, N.; Nakajima, S.; Zaoya, K.; Hamaguchi, F.; Nagasaka, T. Heterocycles 1991, 32, 889-894. (g) Pilli, R. A.; Dias, L. C. Synth. Commun. 1991, 21 2213-2229 (h) Ghiaci, M.; Adibi, M. Org. Prep. Proced. Int. 1996, 28, 474-477. For asymmetric synthesis see: (i) Beyerman, H. C.; Eveleens, W.; Muller, Y. M. F. Recl. Trav. Chim. Pays-Bas 1956, 75, 63-75. (j) Beyerman, H. C.; Eenshuistra, J.; Eveleens, W.; Zweistra, A. Recl. Trav. Chim. Pays-Bas 1959, 78, 43-58. (k) Schöpf, C.; Dummer, G.; Wüst, W. Liebigs Ann. Chem. 1959, 626, 134-1149. (l) Wakabayashi, T.; Watanabe, K.; Kato, Y.; Saito, M. Chem. Lett. 1977, 223-228. (m) Irie, K.; Aoe, K.; Tanaka, T.; Saito, S. J. Chem. Soc., Chem. Commun. 1985, 633-635. (n) Wanner, K. T.; Kärtner, A. Heterocycles 1987, 26, 921-924. (o) Wanner, K. T.; Kärtner, A. Arch. Pharm. 1987, 320, 1253-1267. (p) Pyne, S. G.; Bloem, P.; Chapman, S. L.; Dixon, C. E.; Griffith, R. J. Org. Chem. 1990, 55, 1086-1093. (q) Kiguchi, T.; Nakazono, Y.; Kotera, S.; Ninomiya, I.; Naito, T. Heterocycles 1990, 31, 1525-1535. (r) Comins, D. L.; Hong, H. J. Org. Chem. 1993, 58, 5035-5036. (s) Poerwono, H.; Higashiyama, K.; Takahashi, H. Heterocycles 1998, 47, 263-270. (t) Yu, C.-Y.; Meth-Cohn, O. Tetrahedron Lett. 1999, 40, 6665-6668. (u) Meth-Cohn, O.; Yau, C. C.; Yu, C.-Y. J. Heterocycl. Chem. 1999, 36, 1549-1553. (v) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. Synlett 2000, 1461-1463. (w) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. J. Org. Chem. 2002, 67, 1982-1992.
21. For racemic syntheses ofsedamine, see: (a) Tufariello, J. J.; Ali, S. A. Tetrahedron Lett. 1978, 47, 4647-4650 (b) Shono T.; Matsumura Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176. (c) Hootelé, C.; Ibebeke-Bomangwa, W.; Driessens, F.; Sabil, S. Bull. Soc. Chim. Belg. 1987, 96, 57-61. (d) Tirel, P. J.; Vaultier, M.; Carrie, R. Tetrahedron Lett. 1989, 30, 1947-1950. (e) Driessens, F.; Hootelé, C. Can. J. Chem. 1991, 69, 211-217. (f) Ozawa, N.; Nakajima, S.; Zaoya, K.; Hamaguchi, F.; Nagasaka, T. Heterocycles 1991, 32, 889-894. (g) Pilli, R. A.; Dias, L. C. Synth. Commun. 1991, 21 2213-2229 (h) Ghiaci, M.; Adibi, M. Org. Prep. Proced. Int. 1996, 28, 474-477. For asymmetric synthesis see: (i) Beyerman, H. C.; Eveleens, W.; Muller, Y. M. F. Recl. Trav. Chim. Pays-Bas 1956, 75, 63-75. (j) Beyerman, H. C.; Eenshuistra, J.; Eveleens, W.; Zweistra, A. Recl. Trav. Chim. Pays-Bas 1959, 78, 43-58. (k) Schöpf, C.; Dummer, G.; Wüst, W. Liebigs Ann. Chem. 1959, 626, 134-1149. (l) Wakabayashi, T.; Watanabe, K.; Kato, Y.; Saito, M. Chem. Lett. 1977, 223-228. (m) Irie, K.; Aoe, K.; Tanaka, T.; Saito, S. J. Chem. Soc., Chem. Commun. 1985, 633-635. (n) Wanner, K. T.; Kärtner, A. Heterocycles 1987, 26, 921-924. (o) Wanner, K. T.; Kärtner, A. Arch. Pharm. 1987, 320, 1253-1267. (p) Pyne, S. G.; Bloem, P.; Chapman, S. L.; Dixon, C. E.; Griffith, R. J. Org. Chem. 1990, 55, 1086-1093. (q) Kiguchi, T.; Nakazono, Y.; Kotera, S.; Ninomiya, I.; Naito, T. Heterocycles 1990, 31, 1525-1535. (r) Comins, D. L.; Hong, H. J. Org. Chem. 1993, 58, 5035-5036. (s) Poerwono, H.; Higashiyama, K.; Takahashi, H. Heterocycles 1998, 47, 263-270. (t) Yu, C.-Y.; Meth-Cohn, O. Tetrahedron Lett. 1999, 40, 6665-6668. (u) Meth-Cohn, O.; Yau, C. C.; Yu, C.-Y. J. Heterocycl. Chem. 1999, 36, 1549-1553. (v) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. Synlett 2000, 1461-1463. (w) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. J. Org. Chem. 2002, 67, 1982-1992.
22. For racemic syntheses ofsedamine, see: (a) Tufariello, J. J.; Ali, S. A. Tetrahedron Lett. 1978, 47, 4647-4650 (b) Shono T.; Matsumura Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176. (c) Hootelé, C.; Ibebeke-Bomangwa, W.; Driessens, F.; Sabil, S. Bull. Soc. Chim. Belg. 1987, 96, 57-61. (d) Tirel, P. J.; Vaultier, M.; Carrie, R. Tetrahedron Lett. 1989, 30, 1947-1950. (e) Driessens, F.; Hootelé, C. Can. J. Chem. 1991, 69, 211-217. (f) Ozawa, N.; Nakajima, S.; Zaoya, K.; Hamaguchi, F.; Nagasaka, T. Heterocycles 1991, 32, 889-894. (g) Pilli, R. A.; Dias, L. C. Synth. Commun. 1991, 21 2213-2229 (h) Ghiaci, M.; Adibi, M. Org. Prep. Proced. Int. 1996, 28, 474-477. For asymmetric synthesis see: (i) Beyerman, H. C.; Eveleens, W.; Muller, Y. M. F. Recl. Trav. Chim. Pays-Bas 1956, 75, 63-75. (j) Beyerman, H. C.; Eenshuistra, J.; Eveleens, W.; Zweistra, A. Recl. Trav. Chim. Pays-Bas 1959, 78, 43-58. (k) Schöpf, C.; Dummer, G.; Wüst, W. Liebigs Ann. Chem. 1959, 626, 134-1149. (l) Wakabayashi, T.; Watanabe, K.; Kato, Y.; Saito, M. Chem. Lett. 1977, 223-228. (m) Irie, K.; Aoe, K.; Tanaka, T.; Saito, S. J. Chem. Soc., Chem. Commun. 1985, 633-635. (n) Wanner, K. T.; Kärtner, A. Heterocycles 1987, 26, 921-924. (o) Wanner, K. T.; Kärtner, A. Arch. Pharm. 1987, 320, 1253-1267. (p) Pyne, S. G.; Bloem, P.; Chapman, S. L.; Dixon, C. E.; Griffith, R. J. Org. Chem. 1990, 55, 1086-1093. (q) Kiguchi, T.; Nakazono, Y.; Kotera, S.; Ninomiya, I.; Naito, T. Heterocycles 1990, 31, 1525-1535. (r) Comins, D. L.; Hong, H. J. Org. Chem. 1993, 58, 5035-5036. (s) Poerwono, H.; Higashiyama, K.; Takahashi, H. Heterocycles 1998, 47, 263-270. (t) Yu, C.-Y.; Meth-Cohn, O. Tetrahedron Lett. 1999, 40, 6665-6668. (u) Meth-Cohn, O.; Yau, C. C.; Yu, C.-Y. J. Heterocycl. Chem. 1999, 36, 1549-1553. (v) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. Synlett 2000, 1461-1463. (w) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. J. Org. Chem. 2002, 67, 1982-1992.
23. For racemic syntheses ofsedamine, see: (a) Tufariello, J. J.; Ali, S. A. Tetrahedron Lett. 1978, 47, 4647-4650 (b) Shono T.; Matsumura Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176. (c) Hootelé, C.; Ibebeke-Bomangwa, W.; Driessens, F.; Sabil, S. Bull. Soc. Chim. Belg. 1987, 96, 57-61. (d) Tirel, P. J.; Vaultier, M.; Carrie, R. Tetrahedron Lett. 1989, 30, 1947-1950. (e) Driessens, F.; Hootelé, C. Can. J. Chem. 1991, 69, 211-217. (f) Ozawa, N.; Nakajima, S.; Zaoya, K.; Hamaguchi, F.; Nagasaka, T. Heterocycles 1991, 32, 889-894. (g) Pilli, R. A.; Dias, L. C. Synth. Commun. 1991, 21 2213-2229 (h) Ghiaci, M.; Adibi, M. Org. Prep. Proced. Int. 1996, 28, 474-477. For asymmetric synthesis see: (i) Beyerman, H. C.; Eveleens, W.; Muller, Y. M. F. Recl. Trav. Chim. Pays-Bas 1956, 75, 63-75. (j) Beyerman, H. C.; Eenshuistra, J.; Eveleens, W.; Zweistra, A. Recl. Trav. Chim. Pays-Bas 1959, 78, 43-58. (k) Schöpf, C.; Dummer, G.; Wüst, W. Liebigs Ann. Chem. 1959, 626, 134-1149. (l) Wakabayashi, T.; Watanabe, K.; Kato, Y.; Saito, M. Chem. Lett. 1977, 223-228. (m) Irie, K.; Aoe, K.; Tanaka, T.; Saito, S. J. Chem. Soc., Chem. Commun. 1985, 633-635. (n) Wanner, K. T.; Kärtner, A. Heterocycles 1987, 26, 921-924. (o) Wanner, K. T.; Kärtner, A. Arch. Pharm. 1987, 320, 1253-1267. (p) Pyne, S. G.; Bloem, P.; Chapman, S. L.; Dixon, C. E.; Griffith, R. J. Org. Chem. 1990, 55, 1086-1093. (q) Kiguchi, T.; Nakazono, Y.; Kotera, S.; Ninomiya, I.; Naito, T. Heterocycles 1990, 31, 1525-1535. (r) Comins, D. L.; Hong, H. J. Org. Chem. 1993, 58, 5035-5036. (s) Poerwono, H.; Higashiyama, K.; Takahashi, H. Heterocycles 1998, 47, 263-270. (t) Yu, C.-Y.; Meth-Cohn, O. Tetrahedron Lett. 1999, 40, 6665-6668. (u) Meth-Cohn, O.; Yau, C. C.; Yu, C.-Y. J. Heterocycl. Chem. 1999, 36, 1549-1553. (v) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. Synlett 2000, 1461-1463. (w) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. J. Org. Chem. 2002, 67, 1982-1992.
24. For racemic syntheses ofsedamine, see: (a) Tufariello, J. J.; Ali, S. A. Tetrahedron Lett. 1978, 47, 4647-4650 (b) Shono T.; Matsumura Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176. (c) Hootelé, C.; Ibebeke-Bomangwa, W.; Driessens, F.; Sabil, S. Bull. Soc. Chim. Belg. 1987, 96, 57-61. (d) Tirel, P. J.; Vaultier, M.; Carrie, R. Tetrahedron Lett. 1989, 30, 1947-1950. (e) Driessens, F.; Hootelé, C. Can. J. Chem. 1991, 69, 211-217. (f) Ozawa, N.; Nakajima, S.; Zaoya, K.; Hamaguchi, F.; Nagasaka, T. Heterocycles 1991, 32, 889-894. (g) Pilli, R. A.; Dias, L. C. Synth. Commun. 1991, 21 2213-2229 (h) Ghiaci, M.; Adibi, M. Org. Prep. Proced. Int. 1996, 28, 474-477. For asymmetric synthesis see: (i) Beyerman, H. C.; Eveleens, W.; Muller, Y. M. F. Recl. Trav. Chim. Pays-Bas 1956, 75, 63-75. (j) Beyerman, H. C.; Eenshuistra, J.; Eveleens, W.; Zweistra, A. Recl. Trav. Chim. Pays-Bas 1959, 78, 43-58. (k) Schöpf, C.; Dummer, G.; Wüst, W. Liebigs Ann. Chem. 1959, 626, 134-1149. (l) Wakabayashi, T.; Watanabe, K.; Kato, Y.; Saito, M. Chem. Lett. 1977, 223-228. (m) Irie, K.; Aoe, K.; Tanaka, T.; Saito, S. J. Chem. Soc., Chem. Commun. 1985, 633-635. (n) Wanner, K. T.; Kärtner, A. Heterocycles 1987, 26, 921-924. (o) Wanner, K. T.; Kärtner, A. Arch. Pharm. 1987, 320, 1253-1267. (p) Pyne, S. G.; Bloem, P.; Chapman, S. L.; Dixon, C. E.; Griffith, R. J. Org. Chem. 1990, 55, 1086-1093. (q) Kiguchi, T.; Nakazono, Y.; Kotera, S.; Ninomiya, I.; Naito, T. Heterocycles 1990, 31, 1525-1535. (r) Comins, D. L.; Hong, H. J. Org. Chem. 1993, 58, 5035-5036. (s) Poerwono, H.; Higashiyama, K.; Takahashi, H. Heterocycles 1998, 47, 263-270. (t) Yu, C.-Y.; Meth-Cohn, O. Tetrahedron Lett. 1999, 40, 6665-6668. (u) Meth-Cohn, O.; Yau, C. C.; Yu, C.-Y. J. Heterocycl. Chem. 1999, 36, 1549-1553. (v) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. Synlett 2000, 1461-1463. (w) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. J. Org. Chem. 2002, 67, 1982-1992.
25. For racemic syntheses ofsedamine, see: (a) Tufariello, J. J.; Ali, S. A. Tetrahedron Lett. 1978, 47, 4647-4650 (b) Shono T.; Matsumura Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176. (c) Hootelé, C.; Ibebeke-Bomangwa, W.; Driessens, F.; Sabil, S. Bull. Soc. Chim. Belg. 1987, 96, 57-61. (d) Tirel, P. J.; Vaultier, M.; Carrie, R. Tetrahedron Lett. 1989, 30, 1947-1950. (e) Driessens, F.; Hootelé, C. Can. J. Chem. 1991, 69, 211-217. (f) Ozawa, N.; Nakajima, S.; Zaoya, K.; Hamaguchi, F.; Nagasaka, T. Heterocycles 1991, 32, 889-894. (g) Pilli, R. A.; Dias, L. C. Synth. Commun. 1991, 21 2213-2229 (h) Ghiaci, M.; Adibi, M. Org. Prep. Proced. Int. 1996, 28, 474-477. For asymmetric synthesis see: (i) Beyerman, H. C.; Eveleens, W.; Muller, Y. M. F. Recl. Trav. Chim. Pays-Bas 1956, 75, 63-75. (j) Beyerman, H. C.; Eenshuistra, J.; Eveleens, W.; Zweistra, A. Recl. Trav. Chim. Pays-Bas 1959, 78, 43-58. (k) Schöpf, C.; Dummer, G.; Wüst, W. Liebigs Ann. Chem. 1959, 626, 134-1149. (l) Wakabayashi, T.; Watanabe, K.; Kato, Y.; Saito, M. Chem. Lett. 1977, 223-228. (m) Irie, K.; Aoe, K.; Tanaka, T.; Saito, S. J. Chem. Soc., Chem. Commun. 1985, 633-635. (n) Wanner, K. T.; Kärtner, A. Heterocycles 1987, 26, 921-924. (o) Wanner, K. T.; Kärtner, A. Arch. Pharm. 1987, 320, 1253-1267. (p) Pyne, S. G.; Bloem, P.; Chapman, S. L.; Dixon, C. E.; Griffith, R. J. Org. Chem. 1990, 55, 1086-1093. (q) Kiguchi, T.; Nakazono, Y.; Kotera, S.; Ninomiya, I.; Naito, T. Heterocycles 1990, 31, 1525-1535. (r) Comins, D. L.; Hong, H. J. Org. Chem. 1993, 58, 5035-5036. (s) Poerwono, H.; Higashiyama, K.; Takahashi, H. Heterocycles 1998, 47, 263-270. (t) Yu, C.-Y.; Meth-Cohn, O. Tetrahedron Lett. 1999, 40, 6665-6668. (u) Meth-Cohn, O.; Yau, C. C.; Yu, C.-Y. J. Heterocycl. Chem. 1999, 36, 1549-1553. (v) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. Synlett 2000, 1461-1463. (w) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. J. Org. Chem. 2002, 67, 1982-1992.
26. For racemic syntheses ofsedamine, see: (a) Tufariello, J. J.; Ali, S. A. Tetrahedron Lett. 1978, 47, 4647-4650 (b) Shono T.; Matsumura Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176. (c) Hootelé, C.; Ibebeke-Bomangwa, W.; Driessens, F.; Sabil, S. Bull. Soc. Chim. Belg. 1987, 96, 57-61. (d) Tirel, P. J.; Vaultier, M.; Carrie, R. Tetrahedron Lett. 1989, 30, 1947-1950. (e) Driessens, F.; Hootelé, C. Can. J. Chem. 1991, 69, 211-217. (f) Ozawa, N.; Nakajima, S.; Zaoya, K.; Hamaguchi, F.; Nagasaka, T. Heterocycles 1991, 32, 889-894. (g) Pilli, R. A.; Dias, L. C. Synth. Commun. 1991, 21 2213-2229 (h) Ghiaci, M.; Adibi, M. Org. Prep. Proced. Int. 1996, 28, 474-477. For asymmetric synthesis see: (i) Beyerman, H. C.; Eveleens, W.; Muller, Y. M. F. Recl. Trav. Chim. Pays-Bas 1956, 75, 63-75. (j) Beyerman, H. C.; Eenshuistra, J.; Eveleens, W.; Zweistra, A. Recl. Trav. Chim. Pays-Bas 1959, 78, 43-58. (k) Schöpf, C.; Dummer, G.; Wüst, W. Liebigs Ann. Chem. 1959, 626, 134-1149. (l) Wakabayashi, T.; Watanabe, K.; Kato, Y.; Saito, M. Chem. Lett. 1977, 223-228. (m) Irie, K.; Aoe, K.; Tanaka, T.; Saito, S. J. Chem. Soc., Chem. Commun. 1985, 633-635. (n) Wanner, K. T.; Kärtner, A. Heterocycles 1987, 26, 921-924. (o) Wanner, K. T.; Kärtner, A. Arch. Pharm. 1987, 320, 1253-1267. (p) Pyne, S. G.; Bloem, P.; Chapman, S. L.; Dixon, C. E.; Griffith, R. J. Org. Chem. 1990, 55, 1086-1093. (q) Kiguchi, T.; Nakazono, Y.; Kotera, S.; Ninomiya, I.; Naito, T. Heterocycles 1990, 31, 1525-1535. (r) Comins, D. L.; Hong, H. J. Org. Chem. 1993, 58, 5035-5036. (s) Poerwono, H.; Higashiyama, K.; Takahashi, H. Heterocycles 1998, 47, 263-270. (t) Yu, C.-Y.; Meth-Cohn, O. Tetrahedron Lett. 1999, 40, 6665-6668. (u) Meth-Cohn, O.; Yau, C. C.; Yu, C.-Y. J. Heterocycl. Chem. 1999, 36, 1549-1553. (v) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. Synlett 2000, 1461-1463. (w) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. J. Org. Chem. 2002, 67, 1982-1992.
27. For racemic syntheses ofsedamine, see: (a) Tufariello, J. J.; Ali, S. A. Tetrahedron Lett. 1978, 47, 4647-4650 (b) Shono T.; Matsumura Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176. (c) Hootelé, C.; Ibebeke-Bomangwa, W.; Driessens, F.; Sabil, S. Bull. Soc. Chim. Belg. 1987, 96, 57-61. (d) Tirel, P. J.; Vaultier, M.; Carrie, R. Tetrahedron Lett. 1989, 30, 1947-1950. (e) Driessens, F.; Hootelé, C. Can. J. Chem. 1991, 69, 211-217. (f) Ozawa, N.; Nakajima, S.; Zaoya, K.; Hamaguchi, F.; Nagasaka, T. Heterocycles 1991, 32, 889-894. (g) Pilli, R. A.; Dias, L. C. Synth. Commun. 1991, 21 2213-2229 (h) Ghiaci, M.; Adibi, M. Org. Prep. Proced. Int. 1996, 28, 474-477. For asymmetric synthesis see: (i) Beyerman, H. C.; Eveleens, W.; Muller, Y. M. F. Recl. Trav. Chim. Pays-Bas 1956, 75, 63-75. (j) Beyerman, H. C.; Eenshuistra, J.; Eveleens, W.; Zweistra, A. Recl. Trav. Chim. Pays-Bas 1959, 78, 43-58. (k) Schöpf, C.; Dummer, G.; Wüst, W. Liebigs Ann. Chem. 1959, 626, 134-1149. (l) Wakabayashi, T.; Watanabe, K.; Kato, Y.; Saito, M. Chem. Lett. 1977, 223-228. (m) Irie, K.; Aoe, K.; Tanaka, T.; Saito, S. J. Chem. Soc., Chem. Commun. 1985, 633-635. (n) Wanner, K. T.; Kärtner, A. Heterocycles 1987, 26, 921-924. (o) Wanner, K. T.; Kärtner, A. Arch. Pharm. 1987, 320, 1253-1267. (p) Pyne, S. G.; Bloem, P.; Chapman, S. L.; Dixon, C. E.; Griffith, R. J. Org. Chem. 1990, 55, 1086-1093. (q) Kiguchi, T.; Nakazono, Y.; Kotera, S.; Ninomiya, I.; Naito, T. Heterocycles 1990, 31, 1525-1535. (r) Comins, D. L.; Hong, H. J. Org. Chem. 1993, 58, 5035-5036. (s) Poerwono, H.; Higashiyama, K.; Takahashi, H. Heterocycles 1998, 47, 263-270. (t) Yu, C.-Y.; Meth-Cohn, O. Tetrahedron Lett. 1999, 40, 6665-6668. (u) Meth-Cohn, O.; Yau, C. C.; Yu, C.-Y. J. Heterocycl. Chem. 1999, 36, 1549-1553. (v) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. Synlett 2000, 1461-1463. (w) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. J. Org. Chem. 2002, 67, 1982-1992.
28. For racemic syntheses ofsedamine, see: (a) Tufariello, J. J.; Ali, S. A. Tetrahedron Lett. 1978, 47, 4647-4650 (b) Shono T.; Matsumura Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176. (c) Hootelé, C.; Ibebeke-Bomangwa, W.; Driessens, F.; Sabil, S. Bull. Soc. Chim. Belg. 1987, 96, 57-61. (d) Tirel, P. J.; Vaultier, M.; Carrie, R. Tetrahedron Lett. 1989, 30, 1947-1950. (e) Driessens, F.; Hootelé, C. Can. J. Chem. 1991, 69, 211-217. (f) Ozawa, N.; Nakajima, S.; Zaoya, K.; Hamaguchi, F.; Nagasaka, T. Heterocycles 1991, 32, 889-894. (g) Pilli, R. A.; Dias, L. C. Synth. Commun. 1991, 21 2213-2229 (h) Ghiaci, M.; Adibi, M. Org. Prep. Proced. Int. 1996, 28, 474-477. For asymmetric synthesis see: (i) Beyerman, H. C.; Eveleens, W.; Muller, Y. M. F. Recl. Trav. Chim. Pays-Bas 1956, 75, 63-75. (j) Beyerman, H. C.; Eenshuistra, J.; Eveleens, W.; Zweistra, A. Recl. Trav. Chim. Pays-Bas 1959, 78, 43-58. (k) Schöpf, C.; Dummer, G.; Wüst, W. Liebigs Ann. Chem. 1959, 626, 134-1149. (l) Wakabayashi, T.; Watanabe, K.; Kato, Y.; Saito, M. Chem. Lett. 1977, 223-228. (m) Irie, K.; Aoe, K.; Tanaka, T.; Saito, S. J. Chem. Soc., Chem. Commun. 1985, 633-635. (n) Wanner, K. T.; Kärtner, A. Heterocycles 1987, 26, 921-924. (o) Wanner, K. T.; Kärtner, A. Arch. Pharm. 1987, 320, 1253-1267. (p) Pyne, S. G.; Bloem, P.; Chapman, S. L.; Dixon, C. E.; Griffith, R. J. Org. Chem. 1990, 55, 1086-1093. (q) Kiguchi, T.; Nakazono, Y.; Kotera, S.; Ninomiya, I.; Naito, T. Heterocycles 1990, 31, 1525-1535. (r) Comins, D. L.; Hong, H. J. Org. Chem. 1993, 58, 5035-5036. (s) Poerwono, H.; Higashiyama, K.; Takahashi, H. Heterocycles 1998, 47, 263-270. (t) Yu, C.-Y.; Meth-Cohn, O. Tetrahedron Lett. 1999, 40, 6665-6668. (u) Meth-Cohn, O.; Yau, C. C.; Yu, C.-Y. J. Heterocycl. Chem. 1999, 36, 1549-1553. (v) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. Synlett 2000, 1461-1463. (w) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. J. Org. Chem. 2002, 67, 1982-1992.
29. For racemic syntheses ofsedamine, see: (a) Tufariello, J. J.; Ali, S. A. Tetrahedron Lett. 1978, 47, 4647-4650 (b) Shono T.; Matsumura Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176. (c) Hootelé, C.; Ibebeke-Bomangwa, W.; Driessens, F.; Sabil, S. Bull. Soc. Chim. Belg. 1987, 96, 57-61. (d) Tirel, P. J.; Vaultier, M.; Carrie, R. Tetrahedron Lett. 1989, 30, 1947-1950. (e) Driessens, F.; Hootelé, C. Can. J. Chem. 1991, 69, 211-217. (f) Ozawa, N.; Nakajima, S.; Zaoya, K.; Hamaguchi, F.; Nagasaka, T. Heterocycles 1991, 32, 889-894. (g) Pilli, R. A.; Dias, L. C. Synth. Commun. 1991, 21 2213-2229 (h) Ghiaci, M.; Adibi, M. Org. Prep. Proced. Int. 1996, 28, 474-477. For asymmetric synthesis see: (i) Beyerman, H. C.; Eveleens, W.; Muller, Y. M. F. Recl. Trav. Chim. Pays-Bas 1956, 75, 63-75. (j) Beyerman, H. C.; Eenshuistra, J.; Eveleens, W.; Zweistra, A. Recl. Trav. Chim. Pays-Bas 1959, 78, 43-58. (k) Schöpf, C.; Dummer, G.; Wüst, W. Liebigs Ann. Chem. 1959, 626, 134-1149. (l) Wakabayashi, T.; Watanabe, K.; Kato, Y.; Saito, M. Chem. Lett. 1977, 223-228. (m) Irie, K.; Aoe, K.; Tanaka, T.; Saito, S. J. Chem. Soc., Chem. Commun. 1985, 633-635. (n) Wanner, K. T.; Kärtner, A. Heterocycles 1987, 26, 921-924. (o) Wanner, K. T.; Kärtner, A. Arch. Pharm. 1987, 320, 1253-1267. (p) Pyne, S. G.; Bloem, P.; Chapman, S. L.; Dixon, C. E.; Griffith, R. J. Org. Chem. 1990, 55, 1086-1093. (q) Kiguchi, T.; Nakazono, Y.; Kotera, S.; Ninomiya, I.; Naito, T. Heterocycles 1990, 31, 1525-1535. (r) Comins, D. L.; Hong, H. J. Org. Chem. 1993, 58, 5035-5036. (s) Poerwono, H.; Higashiyama, K.; Takahashi, H. Heterocycles 1998, 47, 263-270. (t) Yu, C.-Y.; Meth-Cohn, O. Tetrahedron Lett. 1999, 40, 6665-6668. (u) Meth-Cohn, O.; Yau, C. C.; Yu, C.-Y. J. Heterocycl. Chem. 1999, 36, 1549-1553. (v) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. Synlett 2000, 1461-1463. (w) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. J. Org. Chem. 2002, 67, 1982-1992.
30. For racemic syntheses ofsedamine, see: (a) Tufariello, J. J.; Ali, S. A. Tetrahedron Lett. 1978, 47, 4647-4650 (b) Shono T.; Matsumura Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176. (c) Hootelé, C.; Ibebeke-Bomangwa, W.; Driessens, F.; Sabil, S. Bull. Soc. Chim. Belg. 1987, 96, 57-61. (d) Tirel, P. J.; Vaultier, M.; Carrie, R. Tetrahedron Lett. 1989, 30, 1947-1950. (e) Driessens, F.; Hootelé, C. Can. J. Chem. 1991, 69, 211-217. (f) Ozawa, N.; Nakajima, S.; Zaoya, K.; Hamaguchi, F.; Nagasaka, T. Heterocycles 1991, 32, 889-894. (g) Pilli, R. A.; Dias, L. C. Synth. Commun. 1991, 21 2213-2229 (h) Ghiaci, M.; Adibi, M. Org. Prep. Proced. Int. 1996, 28, 474-477. For asymmetric synthesis see: (i) Beyerman, H. C.; Eveleens, W.; Muller, Y. M. F. Recl. Trav. Chim. Pays-Bas 1956, 75, 63-75. (j) Beyerman, H. C.; Eenshuistra, J.; Eveleens, W.; Zweistra, A. Recl. Trav. Chim. Pays-Bas 1959, 78, 43-58. (k) Schöpf, C.; Dummer, G.; Wüst, W. Liebigs Ann. Chem. 1959, 626, 134-1149. (l) Wakabayashi, T.; Watanabe, K.; Kato, Y.; Saito, M. Chem. Lett. 1977, 223-228. (m) Irie, K.; Aoe, K.; Tanaka, T.; Saito, S. J. Chem. Soc., Chem. Commun. 1985, 633-635. (n) Wanner, K. T.; Kärtner, A. Heterocycles 1987, 26, 921-924. (o) Wanner, K. T.; Kärtner, A. Arch. Pharm. 1987, 320, 1253-1267. (p) Pyne, S. G.; Bloem, P.; Chapman, S. L.; Dixon, C. E.; Griffith, R. J. Org. Chem. 1990, 55, 1086-1093. (q) Kiguchi, T.; Nakazono, Y.; Kotera, S.; Ninomiya, I.; Naito, T. Heterocycles 1990, 31, 1525-1535. (r) Comins, D. L.; Hong, H. J. Org. Chem. 1993, 58, 5035-5036. (s) Poerwono, H.; Higashiyama, K.; Takahashi, H. Heterocycles 1998, 47, 263-270. (t) Yu, C.-Y.; Meth-Cohn, O. Tetrahedron Lett. 1999, 40, 6665-6668. (u) Meth-Cohn, O.; Yau, C. C.; Yu, C.-Y. J. Heterocycl. Chem. 1999, 36, 1549-1553. (v) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. Synlett 2000, 1461-1463. (w) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. J. Org. Chem. 2002, 67, 1982-1992.
31. For racemic syntheses ofsedamine, see: (a) Tufariello, J. J.; Ali, S. A. Tetrahedron Lett. 1978, 47, 4647-4650 (b) Shono T.; Matsumura Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176. (c) Hootelé, C.; Ibebeke-Bomangwa, W.; Driessens, F.; Sabil, S. Bull. Soc. Chim. Belg. 1987, 96, 57-61. (d) Tirel, P. J.; Vaultier, M.; Carrie, R. Tetrahedron Lett. 1989, 30, 1947-1950. (e) Driessens, F.; Hootelé, C. Can. J. Chem. 1991, 69, 211-217. (f) Ozawa, N.; Nakajima, S.; Zaoya, K.; Hamaguchi, F.; Nagasaka, T. Heterocycles 1991, 32, 889-894. (g) Pilli, R. A.; Dias, L. C. Synth. Commun. 1991, 21 2213-2229 (h) Ghiaci, M.; Adibi, M. Org. Prep. Proced. Int. 1996, 28, 474-477. For asymmetric synthesis see: (i) Beyerman, H. C.; Eveleens, W.; Muller, Y. M. F. Recl. Trav. Chim. Pays-Bas 1956, 75, 63-75. (j) Beyerman, H. C.; Eenshuistra, J.; Eveleens, W.; Zweistra, A. Recl. Trav. Chim. Pays-Bas 1959, 78, 43-58. (k) Schöpf, C.; Dummer, G.; Wüst, W. Liebigs Ann. Chem. 1959, 626, 134-1149. (l) Wakabayashi, T.; Watanabe, K.; Kato, Y.; Saito, M. Chem. Lett. 1977, 223-228. (m) Irie, K.; Aoe, K.; Tanaka, T.; Saito, S. J. Chem. Soc., Chem. Commun. 1985, 633-635. (n) Wanner, K. T.; Kärtner, A. Heterocycles 1987, 26, 921-924. (o) Wanner, K. T.; Kärtner, A. Arch. Pharm. 1987, 320, 1253-1267. (p) Pyne, S. G.; Bloem, P.; Chapman, S. L.; Dixon, C. E.; Griffith, R. J. Org. Chem. 1990, 55, 1086-1093. (q) Kiguchi, T.; Nakazono, Y.; Kotera, S.; Ninomiya, I.; Naito, T. Heterocycles 1990, 31, 1525-1535. (r) Comins, D. L.; Hong, H. J. Org. Chem. 1993, 58, 5035-5036. (s) Poerwono, H.; Higashiyama, K.; Takahashi, H. Heterocycles 1998, 47, 263-270. (t) Yu, C.-Y.; Meth-Cohn, O. Tetrahedron Lett. 1999, 40, 6665-6668. (u) Meth-Cohn, O.; Yau, C. C.; Yu, C.-Y. J. Heterocycl. Chem. 1999, 36, 1549-1553. (v) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. Synlett 2000, 1461-1463. (w) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. J. Org. Chem. 2002, 67, 1982-1992.
32. For racemic syntheses ofsedamine, see: (a) Tufariello, J. J.; Ali, S. A. Tetrahedron Lett. 1978, 47, 4647-4650 (b) Shono T.; Matsumura Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176. (c) Hootelé, C.; Ibebeke-Bomangwa, W.; Driessens, F.; Sabil, S. Bull. Soc. Chim. Belg. 1987, 96, 57-61. (d) Tirel, P. J.; Vaultier, M.; Carrie, R. Tetrahedron Lett. 1989, 30, 1947-1950. (e) Driessens, F.; Hootelé, C. Can. J. Chem. 1991, 69, 211-217. (f) Ozawa, N.; Nakajima, S.; Zaoya, K.; Hamaguchi, F.; Nagasaka, T. Heterocycles 1991, 32, 889-894. (g) Pilli, R. A.; Dias, L. C. Synth. Commun. 1991, 21 2213-2229 (h) Ghiaci, M.; Adibi, M. Org. Prep. Proced. Int. 1996, 28, 474-477. For asymmetric synthesis see: (i) Beyerman, H. C.; Eveleens, W.; Muller, Y. M. F. Recl. Trav. Chim. Pays-Bas 1956, 75, 63-75. (j) Beyerman, H. C.; Eenshuistra, J.; Eveleens, W.; Zweistra, A. Recl. Trav. Chim. Pays-Bas 1959, 78, 43-58. (k) Schöpf, C.; Dummer, G.; Wüst, W. Liebigs Ann. Chem. 1959, 626, 134-1149. (l) Wakabayashi, T.; Watanabe, K.; Kato, Y.; Saito, M. Chem. Lett. 1977, 223-228. (m) Irie, K.; Aoe, K.; Tanaka, T.; Saito, S. J. Chem. Soc., Chem. Commun. 1985, 633-635. (n) Wanner, K. T.; Kärtner, A. Heterocycles 1987, 26, 921-924. (o) Wanner, K. T.; Kärtner, A. Arch. Pharm. 1987, 320, 1253-1267. (p) Pyne, S. G.; Bloem, P.; Chapman, S. L.; Dixon, C. E.; Griffith, R. J. Org. Chem. 1990, 55, 1086-1093. (q) Kiguchi, T.; Nakazono, Y.; Kotera, S.; Ninomiya, I.; Naito, T. Heterocycles 1990, 31, 1525-1535. (r) Comins, D. L.; Hong, H. J. Org. Chem. 1993, 58, 5035-5036. (s) Poerwono, H.; Higashiyama, K.; Takahashi, H. Heterocycles 1998, 47, 263-270. (t) Yu, C.-Y.; Meth-Cohn, O. Tetrahedron Lett. 1999, 40, 6665-6668. (u) Meth-Cohn, O.; Yau, C. C.; Yu, C.-Y. J. Heterocycl. Chem. 1999, 36, 1549-1553. (v) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. Synlett 2000, 1461-1463. (w) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. J. Org. Chem. 2002, 67, 1982-1992.
33. For racemic syntheses ofsedamine, see: (a) Tufariello, J. J.; Ali, S. A. Tetrahedron Lett. 1978, 47, 4647-4650 (b) Shono T.; Matsumura Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176. (c) Hootelé, C.; Ibebeke-Bomangwa, W.; Driessens, F.; Sabil, S. Bull. Soc. Chim. Belg. 1987, 96, 57-61. (d) Tirel, P. J.; Vaultier, M.; Carrie, R. Tetrahedron Lett. 1989, 30, 1947-1950. (e) Driessens, F.; Hootelé, C. Can. J. Chem. 1991, 69, 211-217. (f) Ozawa, N.; Nakajima, S.; Zaoya, K.; Hamaguchi, F.; Nagasaka, T. Heterocycles 1991, 32, 889-894. (g) Pilli, R. A.; Dias, L. C. Synth. Commun. 1991, 21 2213-2229 (h) Ghiaci, M.; Adibi, M. Org. Prep. Proced. Int. 1996, 28, 474-477. For asymmetric synthesis see: (i) Beyerman, H. C.; Eveleens, W.; Muller, Y. M. F. Recl. Trav. Chim. Pays-Bas 1956, 75, 63-75. (j) Beyerman, H. C.; Eenshuistra, J.; Eveleens, W.; Zweistra, A. Recl. Trav. Chim. Pays-Bas 1959, 78, 43-58. (k) Schöpf, C.; Dummer, G.; Wüst, W. Liebigs Ann. Chem. 1959, 626, 134-1149. (l) Wakabayashi, T.; Watanabe, K.; Kato, Y.; Saito, M. Chem. Lett. 1977, 223-228. (m) Irie, K.; Aoe, K.; Tanaka, T.; Saito, S. J. Chem. Soc., Chem. Commun. 1985, 633-635. (n) Wanner, K. T.; Kärtner, A. Heterocycles 1987, 26, 921-924. (o) Wanner, K. T.; Kärtner, A. Arch. Pharm. 1987, 320, 1253-1267. (p) Pyne, S. G.; Bloem, P.; Chapman, S. L.; Dixon, C. E.; Griffith, R. J. Org. Chem. 1990, 55, 1086-1093. (q) Kiguchi, T.; Nakazono, Y.; Kotera, S.; Ninomiya, I.; Naito, T. Heterocycles 1990, 31, 1525-1535. (r) Comins, D. L.; Hong, H. J. Org. Chem. 1993, 58, 5035-5036. (s) Poerwono, H.; Higashiyama, K.; Takahashi, H. Heterocycles 1998, 47, 263-270. (t) Yu, C.-Y.; Meth-Cohn, O. Tetrahedron Lett. 1999, 40, 6665-6668. (u) Meth-Cohn, O.; Yau, C. C.; Yu, C.-Y. J. Heterocycl. Chem. 1999, 36, 1549-1553. (v) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. Synlett 2000, 1461-1463. (w) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. J. Org. Chem. 2002, 67, 1982-1992.
34. For racemic syntheses ofsedamine, see: (a) Tufariello, J. J.; Ali, S. A. Tetrahedron Lett. 1978, 47, 4647-4650 (b) Shono T.; Matsumura Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176. (c) Hootelé, C.; Ibebeke-Bomangwa, W.; Driessens, F.; Sabil, S. Bull. Soc. Chim. Belg. 1987, 96, 57-61. (d) Tirel, P. J.; Vaultier, M.; Carrie, R. Tetrahedron Lett. 1989, 30, 1947-1950. (e) Driessens, F.; Hootelé, C. Can. J. Chem. 1991, 69, 211-217. (f) Ozawa, N.; Nakajima, S.; Zaoya, K.; Hamaguchi, F.; Nagasaka, T. Heterocycles 1991, 32, 889-894. (g) Pilli, R. A.; Dias, L. C. Synth. Commun. 1991, 21 2213-2229 (h) Ghiaci, M.; Adibi, M. Org. Prep. Proced. Int. 1996, 28, 474-477. For asymmetric synthesis see: (i) Beyerman, H. C.; Eveleens, W.; Muller, Y. M. F. Recl. Trav. Chim. Pays-Bas 1956, 75, 63-75. (j) Beyerman, H. C.; Eenshuistra, J.; Eveleens, W.; Zweistra, A. Recl. Trav. Chim. Pays-Bas 1959, 78, 43-58. (k) Schöpf, C.; Dummer, G.; Wüst, W. Liebigs Ann. Chem. 1959, 626, 134-1149. (l) Wakabayashi, T.; Watanabe, K.; Kato, Y.; Saito, M. Chem. Lett. 1977, 223-228. (m) Irie, K.; Aoe, K.; Tanaka, T.; Saito, S. J. Chem. Soc., Chem. Commun. 1985, 633-635. (n) Wanner, K. T.; Kärtner, A. Heterocycles 1987, 26, 921-924. (o) Wanner, K. T.; Kärtner, A. Arch. Pharm. 1987, 320, 1253-1267. (p) Pyne, S. G.; Bloem, P.; Chapman, S. L.; Dixon, C. E.; Griffith, R. J. Org. Chem. 1990, 55, 1086-1093. (q) Kiguchi, T.; Nakazono, Y.; Kotera, S.; Ninomiya, I.; Naito, T. Heterocycles 1990, 31, 1525-1535. (r) Comins, D. L.; Hong, H. J. Org. Chem. 1993, 58, 5035-5036. (s) Poerwono, H.; Higashiyama, K.; Takahashi, H. Heterocycles 1998, 47, 263-270. (t) Yu, C.-Y.; Meth-Cohn, O. Tetrahedron Lett. 1999, 40, 6665-6668. (u) Meth-Cohn, O.; Yau, C. C.; Yu, C.-Y. J. Heterocycl. Chem. 1999, 36, 1549-1553. (v) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. Synlett 2000, 1461-1463. (w) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. J. Org. Chem. 2002, 67, 1982-1992.
35. For racemic syntheses ofsedamine, see: (a) Tufariello, J. J.; Ali, S. A. Tetrahedron Lett. 1978, 47, 4647-4650 (b) Shono T.; Matsumura Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176. (c) Hootelé, C.; Ibebeke-Bomangwa, W.; Driessens, F.; Sabil, S. Bull. Soc. Chim. Belg. 1987, 96, 57-61. (d) Tirel, P. J.; Vaultier, M.; Carrie, R. Tetrahedron Lett. 1989, 30, 1947-1950. (e) Driessens, F.; Hootelé, C. Can. J. Chem. 1991, 69, 211-217. (f) Ozawa, N.; Nakajima, S.; Zaoya, K.; Hamaguchi, F.; Nagasaka, T. Heterocycles 1991, 32, 889-894. (g) Pilli, R. A.; Dias, L. C. Synth. Commun. 1991, 21 2213-2229 (h) Ghiaci, M.; Adibi, M. Org. Prep. Proced. Int. 1996, 28, 474-477. For asymmetric synthesis see: (i) Beyerman, H. C.; Eveleens, W.; Muller, Y. M. F. Recl. Trav. Chim. Pays-Bas 1956, 75, 63-75. (j) Beyerman, H. C.; Eenshuistra, J.; Eveleens, W.; Zweistra, A. Recl. Trav. Chim. Pays-Bas 1959, 78, 43-58. (k) Schöpf, C.; Dummer, G.; Wüst, W. Liebigs Ann. Chem. 1959, 626, 134-1149. (l) Wakabayashi, T.; Watanabe, K.; Kato, Y.; Saito, M. Chem. Lett. 1977, 223-228. (m) Irie, K.; Aoe, K.; Tanaka, T.; Saito, S. J. Chem. Soc., Chem. Commun. 1985, 633-635. (n) Wanner, K. T.; Kärtner, A. Heterocycles 1987, 26, 921-924. (o) Wanner, K. T.; Kärtner, A. Arch. Pharm. 1987, 320, 1253-1267. (p) Pyne, S. G.; Bloem, P.; Chapman, S. L.; Dixon, C. E.; Griffith, R. J. Org. Chem. 1990, 55, 1086-1093. (q) Kiguchi, T.; Nakazono, Y.; Kotera, S.; Ninomiya, I.; Naito, T. Heterocycles 1990, 31, 1525-1535. (r) Comins, D. L.; Hong, H. J. Org. Chem. 1993, 58, 5035-5036. (s) Poerwono, H.; Higashiyama, K.; Takahashi, H. Heterocycles 1998, 47, 263-270. (t) Yu, C.-Y.; Meth-Cohn, O. Tetrahedron Lett. 1999, 40, 6665-6668. (u) Meth-Cohn, O.; Yau, C. C.; Yu, C.-Y. J. Heterocycl. Chem. 1999, 36, 1549-1553. (v) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. Synlett 2000, 1461-1463. (w) Cossy, J.; Willis, C.; Bellosta, V.; Bouzbouz, S. J. Org. Chem. 2002, 67, 1982-1992.
36. An enantiomeric synthesis of (-)-allosedamine, a diastereoisomer of (-)-sedamine, using this strategy was previously published as a communication; see: Felpin, F.-X.; Lebreton, J. Tetrahedron Lett. 2002, 43, 225-227.
37. Lobeline exists in solution as a cis/trans mixture; see also ref 5.
38. For a review, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293. For representative examples of enantioselective allylations, see: Masamune, S.; Short, R. P. J. Am. Chem. Soc. 1989, 111, 1892-1894. (b) Roush, W. R.; Hoong, L. K.; Palmer. M. A. J.; Park, C. J. J. Org. Chem. 1990, 55, 4109-4117. (c) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827-7828. (d) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723-4724. (e) Loh, T. P.; Zhou, J. R. Tetrahedron Lett. 1999, 40, 9115-9118. (f) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935-1939. For recent applications in total synthesis, see: (a) Provencal D. P.; Gardelli, C.; Lafontaine, J. A.; Leahy, J. W. Tetrahedron Lett. 1995, 36, 6033-6036. (b) Onoda, T.; Shirai, R.; Koiso, Y.; Iwasaki, S. Tetrahedron Lett. 1996, 37, 4397-4400. (c) Yu, W.; Zhang, Y.; Jin, Z. Org. Lett. 2001, 3, 1447-1450. (d) Cossy, J.; Willis, C.; Bellosta, V.; Saint-Jalmes, L. Synthesis 2002, 951-957.
39. For a review, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293. For representative examples of enantioselective allylations, see: Masamune, S.; Short, R. P. J. Am. Chem. Soc. 1989, 111, 1892-1894. (b) Roush, W. R.; Hoong, L. K.; Palmer. M. A. J.; Park, C. J. J. Org. Chem. 1990, 55, 4109-4117. (c) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827-7828. (d) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723-4724. (e) Loh, T. P.; Zhou, J. R. Tetrahedron Lett. 1999, 40, 9115-9118. (f) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935-1939. For recent applications in total synthesis, see: (a) Provencal D. P.; Gardelli, C.; Lafontaine, J. A.; Leahy, J. W. Tetrahedron Lett. 1995, 36, 6033-6036. (b) Onoda, T.; Shirai, R.; Koiso, Y.; Iwasaki, S. Tetrahedron Lett. 1996, 37, 4397-4400. (c) Yu, W.; Zhang, Y.; Jin, Z. Org. Lett. 2001, 3, 1447-1450. (d) Cossy, J.; Willis, C.; Bellosta, V.; Saint-Jalmes, L. Synthesis 2002, 951-957.
40. For a review, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293. For representative examples of enantioselective allylations, see: Masamune, S.; Short, R. P. J. Am. Chem. Soc. 1989, 111, 1892-1894. (b) Roush, W. R.; Hoong, L. K.; Palmer. M. A. J.; Park, C. J. J. Org. Chem. 1990, 55, 4109-4117. (c) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827-7828. (d) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723-4724. (e) Loh, T. P.; Zhou, J. R. Tetrahedron Lett. 1999, 40, 9115-9118. (f) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935-1939. For recent applications in total synthesis, see: (a) Provencal D. P.; Gardelli, C.; Lafontaine, J. A.; Leahy, J. W. Tetrahedron Lett. 1995, 36, 6033-6036. (b) Onoda, T.; Shirai, R.; Koiso, Y.; Iwasaki, S. Tetrahedron Lett. 1996, 37, 4397-4400. (c) Yu, W.; Zhang, Y.; Jin, Z. Org. Lett. 2001, 3, 1447-1450. (d) Cossy, J.; Willis, C.; Bellosta, V.; Saint-Jalmes, L. Synthesis 2002, 951-957.
41. For a review, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293. For representative examples of enantioselective allylations, see: Masamune, S.; Short, R. P. J. Am. Chem. Soc. 1989, 111, 1892-1894. (b) Roush, W. R.; Hoong, L. K.; Palmer. M. A. J.; Park, C. J. J. Org. Chem. 1990, 55, 4109-4117. (c) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827-7828. (d) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723-4724. (e) Loh, T. P.; Zhou, J. R. Tetrahedron Lett. 1999, 40, 9115-9118. (f) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935-1939. For recent applications in total synthesis, see: (a) Provencal D. P.; Gardelli, C.; Lafontaine, J. A.; Leahy, J. W. Tetrahedron Lett. 1995, 36, 6033-6036. (b) Onoda, T.; Shirai, R.; Koiso, Y.; Iwasaki, S. Tetrahedron Lett. 1996, 37, 4397-4400. (c) Yu, W.; Zhang, Y.; Jin, Z. Org. Lett. 2001, 3, 1447-1450. (d) Cossy, J.; Willis, C.; Bellosta, V.; Saint-Jalmes, L. Synthesis 2002, 951-957.
42. For a review, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293. For representative examples of enantioselective allylations, see: Masamune, S.; Short, R. P. J. Am. Chem. Soc. 1989, 111, 1892-1894. (b) Roush, W. R.; Hoong, L. K.; Palmer. M. A. J.; Park, C. J. J. Org. Chem. 1990, 55, 4109-4117. (c) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827-7828. (d) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723-4724. (e) Loh, T. P.; Zhou, J. R. Tetrahedron Lett. 1999, 40, 9115-9118. (f) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935-1939. For recent applications in total synthesis, see: (a) Provencal D. P.; Gardelli, C.; Lafontaine, J. A.; Leahy, J. W. Tetrahedron Lett. 1995, 36, 6033-6036. (b) Onoda, T.; Shirai, R.; Koiso, Y.; Iwasaki, S. Tetrahedron Lett. 1996, 37, 4397-4400. (c) Yu, W.; Zhang, Y.; Jin, Z. Org. Lett. 2001, 3, 1447-1450. (d) Cossy, J.; Willis, C.; Bellosta, V.; Saint-Jalmes, L. Synthesis 2002, 951-957.
43. For a review, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293. For representative examples of enantioselective allylations, see: Masamune, S.; Short, R. P. J. Am. Chem. Soc. 1989, 111, 1892-1894. (b) Roush, W. R.; Hoong, L. K.; Palmer. M. A. J.; Park, C. J. J. Org. Chem. 1990, 55, 4109-4117. (c) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827-7828. (d) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723-4724. (e) Loh, T. P.; Zhou, J. R. Tetrahedron Lett. 1999, 40, 9115-9118. (f) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935-1939. For recent applications in total synthesis, see: (a) Provencal D. P.; Gardelli, C.; Lafontaine, J. A.; Leahy, J. W. Tetrahedron Lett. 1995, 36, 6033-6036. (b) Onoda, T.; Shirai, R.; Koiso, Y.; Iwasaki, S. Tetrahedron Lett. 1996, 37, 4397-4400. (c) Yu, W.; Zhang, Y.; Jin, Z. Org. Lett. 2001, 3, 1447-1450. (d) Cossy, J.; Willis, C.; Bellosta, V.; Saint-Jalmes, L. Synthesis 2002, 951-957.
44. For a review, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293. For representative examples of enantioselective allylations, see: Masamune, S.; Short, R. P. J. Am. Chem. Soc. 1989, 111, 1892-1894. (b) Roush, W. R.; Hoong, L. K.; Palmer. M. A. J.; Park, C. J. J. Org. Chem. 1990, 55, 4109-4117. (c) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827-7828. (d) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723-4724. (e) Loh, T. P.; Zhou, J. R. Tetrahedron Lett. 1999, 40, 9115-9118. (f) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935-1939. For recent applications in total synthesis, see: (a) Provencal D. P.; Gardelli, C.; Lafontaine, J. A.; Leahy, J. W. Tetrahedron Lett. 1995, 36, 6033-6036. (b) Onoda, T.; Shirai, R.; Koiso, Y.; Iwasaki, S. Tetrahedron Lett. 1996, 37, 4397-4400. (c) Yu, W.; Zhang, Y.; Jin, Z. Org. Lett. 2001, 3, 1447-1450. (d) Cossy, J.; Willis, C.; Bellosta, V.; Saint-Jalmes, L. Synthesis 2002, 951-957.
45. For a review, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293. For representative examples of enantioselective allylations, see: Masamune, S.; Short, R. P. J. Am. Chem. Soc. 1989, 111, 1892-1894. (b) Roush, W. R.; Hoong, L. K.; Palmer. M. A. J.; Park, C. J. J. Org. Chem. 1990, 55, 4109-4117. (c) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827-7828. (d) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723-4724. (e) Loh, T. P.; Zhou, J. R. Tetrahedron Lett. 1999, 40, 9115-9118. (f) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935-1939. For recent applications in total synthesis, see: (a) Provencal D. P.; Gardelli, C.; Lafontaine, J. A.; Leahy, J. W. Tetrahedron Lett. 1995, 36, 6033-6036. (b) Onoda, T.; Shirai, R.; Koiso, Y.; Iwasaki, S. Tetrahedron Lett. 1996, 37, 4397-4400. (c) Yu, W.; Zhang, Y.; Jin, Z. Org. Lett. 2001, 3, 1447-1450. (d) Cossy, J.; Willis, C.; Bellosta, V.; Saint-Jalmes, L. Synthesis 2002, 951-957.
46. For a review, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293. For representative examples of enantioselective allylations, see: Masamune, S.; Short, R. P. J. Am. Chem. Soc. 1989, 111, 1892-1894. (b) Roush, W. R.; Hoong, L. K.; Palmer. M. A. J.; Park, C. J. J. Org. Chem. 1990, 55, 4109-4117. (c) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827-7828. (d) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723-4724. (e) Loh, T. P.; Zhou, J. R. Tetrahedron Lett. 1999, 40, 9115-9118. (f) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935-1939. For recent applications in total synthesis, see: (a) Provencal D. P.; Gardelli, C.; Lafontaine, J. A.; Leahy, J. W. Tetrahedron Lett. 1995, 36, 6033-6036. (b) Onoda, T.; Shirai, R.; Koiso, Y.; Iwasaki, S. Tetrahedron Lett. 1996, 37, 4397-4400. (c) Yu, W.; Zhang, Y.; Jin, Z. Org. Lett. 2001, 3, 1447-1450. (d) Cossy, J.; Willis, C.; Bellosta, V.; Saint-Jalmes, L. Synthesis 2002, 951-957.
47. For a review, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293. For representative examples of enantioselective allylations, see: Masamune, S.; Short, R. P. J. Am. Chem. Soc. 1989, 111, 1892-1894. (b) Roush, W. R.; Hoong, L. K.; Palmer. M. A. J.; Park, C. J. J. Org. Chem. 1990, 55, 4109-4117. (c) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827-7828. (d) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723-4724. (e) Loh, T. P.; Zhou, J. R. Tetrahedron Lett. 1999, 40, 9115-9118. (f) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935-1939. For recent applications in total synthesis, see: (a) Provencal D. P.; Gardelli, C.; Lafontaine, J. A.; Leahy, J. W. Tetrahedron Lett. 1995, 36, 6033-6036. (b) Onoda, T.; Shirai, R.; Koiso, Y.; Iwasaki, S. Tetrahedron Lett. 1996, 37, 4397-4400. (c) Yu, W.; Zhang, Y.; Jin, Z. Org. Lett. 2001, 3, 1447-1450. (d) Cossy, J.; Willis, C.; Bellosta, V.; Saint-Jalmes, L. Synthesis 2002, 951-957.
48. For a review, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293. For representative examples of enantioselective allylations, see: Masamune, S.; Short, R. P. J. Am. Chem. Soc. 1989, 111, 1892-1894. (b) Roush, W. R.; Hoong, L. K.; Palmer. M. A. J.; Park, C. J. J. Org. Chem. 1990, 55, 4109-4117. (c) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827-7828. (d) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723-4724. (e) Loh, T. P.; Zhou, J. R. Tetrahedron Lett. 1999, 40, 9115-9118. (f) Kii, S.; Maruoka, K. Tetrahedron Lett. 2001, 42, 1935-1939. For recent applications in total synthesis, see: (a) Provencal D. P.; Gardelli, C.; Lafontaine, J. A.; Leahy, J. W. Tetrahedron Lett. 1995, 36, 6033-6036. (b) Onoda, T.; Shirai, R.; Koiso, Y.; Iwasaki, S. Tetrahedron Lett. 1996, 37, 4397-4400. (c) Yu, W.; Zhang, Y.; Jin, Z. Org. Lett. 2001, 3, 1447-1450. (d) Cossy, J.; Willis, C.; Bellosta, V.; Saint-Jalmes, L. Synthesis 2002, 951-957.
49. (a) Racherla, U. S.; Brown, H. C. J. Org. Chem. 1991, 56, 401-404.
50. (b) Racherla, U. S.; Liao, Y.; Brown, H. C. J. Org. Chem. 1992, 57, 6614-6617.
51. DIP-Chloride is a trademark of Aldrich Chemical Co.
52. Felpin, F.-X.; Bertrand, M.-J.; Lebreton, J. Tetrahedron 2002, 58, 7381-7389.
53. All enantiomeric excesses were determined by chiral HPLC analysis on a Chiralcel OD-H column, 46 x 15 cm.
54. For reviews on enantioselective reduction of prochiral ketones, see: (a) Singh, V. K. Synthesis 1992, 605-617.
55. (b) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1992, 3, 1475-1504.
56. (c) Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. 1998, 37, 1986-2012.
57. This β,γ-unsaturated aryl ketone, 8, is quite sensitive to basic or acidic treatment, as well as purification on silica gel, and evolved slowly to the more stable α,β-unsaturated compound. However, when this crude material was immediately engaged in the next step, no side reaction occurred.
58. (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156.
59. (b) Meyer, S. D.; Schreiber, S. L. J. Org. Chem. 1994, 59, 7549-7552.
60. (c) Boeckmann, R. K., Jr.; Shao, P.; Mullins, J. J. Org. Synth. 1999, 77, 141-152.
61. This compound was >95% pure as judged from proton NMR analysis.
62. Other oxidations such as with Jones reagent or PCC failed to give β,γ-unsaturated aryl ketone 8.
63. Mathre, D. J.; Thompson, A. S.; Douglas, A. W.; Hoogsteen, K.; Carroll, J. D.; Corley, E. G.; Grabowski, E. J. J. J. Org. Chem. 1993, 58,
64. (a) Lipshutz, B. H.; Kotsuki, H.; Lew, W. Tetrahedron Lett. 1986, 27, 4825-4828.
65. (b) Guo, J.; Duffy, K. J.; Stevens, K. L.; Dalko, P. I.; Roth, R. M.; Hayward, M. M.; Kishi, Y. Angew. Chem., Int. Ed. 1998, 37, 187-192.
66. (c) Hayward, M. M.; Roth, R. M.; Duffy, K. J.; Dalko, P. I.; Stevens, K. L.; Guo, J.; Kishi, Y. Angew. Chem., Int. Ed. 1998, 37, 192-196.
67. Epoxidation of homoallylic alcohol -4 with m-chloroperbenzoic acid proceeded without diastereoselectivity.
68. Sharpless K. B.; Michaelson, R. C. J. Am. Chem. Soc. 1973, 95, 6136-6137.
69. Mihelich has shown that this method gave much higher diastereoselectivity with 2-substituted homoallylic alcohols with a cis-double bond: Mihelich, E. D.; Daniels, K.; Eickhoff, D. J. J. Am. Chem. Soc. 1981, 103, 7690-7692.
70. The absolute configuration of the major diastereoisomer was assigned as (1R,3S) by analogy with the literature and in accord with the proposed mechanism.
71. The mixture of the two diastereoisomers could not be resolved on a silica gel column.
72. Bongini, A.; Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Org. Chem. 1982, 47, 4626-4633.
73. Duan, J. J.-W.; Smith, A. B., III. J. Org. Chem. 1993, 58, 3703-3711.
74. Under Smith's conditions compound 9 was isolated with similar yield. However, the use of n-BuLi on a large scale is less convenient.
75. To confirm this high selectivity, a sample of a racemic mixture of syn/anti-3,4-epoxy alcohol (1/1) was prepared via epoxidation of the racemic homoallylic alcohol 4 with mCPBA.
76. 3 in methanol. Unfortunately, the desired compound was accompanied by substantial amounts of undefined products, which greatly complicated the purification on a silica gel column.
77. (a) Mitsunobu, O. Synthesis 1981, 1-28.
78. (b) Dodge, J. A.; Trujillo, J. I.; Presnell, M. J. Org. Chem. 1994, 59, 234-236.
79. The regioselectivity of cuprate attack observed was significantly dependent on the temperature: at -40 °C only the desired regioisomer was formed.
80. This failure is not so surprising since the 1-azide-4-alkenes are prone to intramolecular [2 + 3] dipolar cycloaddition at high temperature (above 80 °C) to form a thermally labile triazoline, which may undergo a 1,2-hydrogen shift with nitrogen loss to give a 1-pyrroline; see: Pearson, W. H.; Lin, K.-C. Tetrahedron Lett. 1990, 31, 7571-7574.
81. Lal, B.; Pramanik, B. N.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1977, 1977-1980.
82. This intramolecular 1,3-dipolar cycloaddition reaction occurring on 1-azide-4-alkenes seems to be very substrate dependent. In some cases, it is possible by working quickly to obtain the azide in correct yield. See: Taber, D. F.; Rahimizadeh, M.; You, K. K. J. Org. Chem. 1995, 60, 529-531.
83. Busacca, C. A.; Grossbach, D.; Spinelli, E. Tetrahedron: Asymmetry 2000, 11, 1907-1910.
84. A. De Mesmaeker, A.; Waldner, A.; Lebreton, J.; Hoffmann, P.; Freirer, S. M.; Fritsch, V.; Wolf, R. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 226-229.
85. For selected examples of cyclization, see: (a) Han, G.; LaPorte, M. G.; Folmer, J. J.; Werner, K. M.; Weinreb, S. M. J. Org. Chem. 2000, 65, 6293-6306. (b) Razavi, H.; Polt, R. J. Org. Chem. 2000, 65, 5693-5706.
86. For selected examples of cyclization, see: (a) Han, G.; LaPorte, M. G.; Folmer, J. J.; Werner, K. M.; Weinreb, S. M. J. Org. Chem. 2000, 65, 6293-6306. (b) Razavi, H.; Polt, R. J. Org. Chem. 2000, 65, 5693-5706.
87. Domínguez, C.; Csákÿ, A. G.; Magano, J.; Plumet, J. Synthesis 1989, 172-175.
88. Ebnöther, A. Helv. Chim. Acta. 1955, 38, 386-396.
89. Marazano et al. described similar phenomena on the lobeline hydrochloride salt; see ref 5.
90. Watson, S. C.; Eastham, J. F. J. Organomet. Chem. 1967, 165-168.
91. Jadhav, P. K.; Bhat, K. S.; Perumal, T.; Brown, H. C. J. Org. Chem. 1986, 51, 432-439.