An efficient total synthesis of (±)-lycoramine

Organic Letters

Volumn 6, Issue 25, 2004, Pages 4691-4694

  Fan, Chun An ^a   Tu, Yong Qiang ^a   Song, Zhen Lei ^a   Zhang, En ^a   Shi, Lei ^a   Wang, Min ^a   Wang, Baomin ^a   Zhang, Shu Yu ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKALOID DERIVATIVE; CARBON; LYCORAMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

AMARYLLIDACEAE ALKALOIDS; CYCLIZATION; MOLECULAR STRUCTURE; PROPANOLS; STEREOISOMERISM;

EID: 11444249264     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048105k     Document Type: Article

References (39)

1. Lycoramine as an Amaryllidaceae alkaloid was first isolated from Lycoris radiata by Kondo, Tomimura, and Ishiwata; see: (a) Kondo, H.; Tomimura, K.; Ishiwata, S. J. Pharm. Soc. Jpn. 1932, 52, 51. For the synthesis of lycoramine, see: (b) Barton, D. H. R. G.; Kirby, W. J. Chem. Soc. 1962, 806. (c) Hazama, N.; Irie, H.; Mizutani, T.; Shingu, T.; Takada, M.; Uyeo, S. J. Chem. Soc. C 1968, 2947. (d) Misaka, Y.; Mizutani, T.; Sekido, M.; Uyeo, S. J. Chem. Soc. C 1968, 2954. (e) Schultz, A. G.; Yee, Y. K.; Berger, M. H. J. Am. Chem. Soc. 1977, 99, 8065. (f) Martin, S. F.; Garrison, P. J. J. Org. Chem. 1981, 46, 3567. (g) Martin, S. F.; Garrison, P. J. J. Org. Chem. 1982, 47, 1513. (h) Sánchez, I. H.; Soria, J. J.; López, F. J.; Larraza, M. I.; Flores, H. J. J. Org. Chem. 1984, 49, 157. (i) Ackland, D. J.; Pinhey, J. T. J. Chem. Soc., Perkin Trans. 1 1987, 2695. (j) Parker, K. A.; Kim, H.-J. J. Org. Chem. 1992, 57, 752. (k) Ishizaki, M.; Ozaki, K.; Kanematsu, A.; Isoda, T.; Hoshino, O. J. Org. Chem. 1993, 58, 3877. (l) Kita, Y.; Arisawa, M.; Gyoten, M.; Nakajima, M.; Hamada, R.; Tohma, H.; Takada, T. J. Org. Chem. 1998, 63, 6625. (m) Gras, E.; Guillou, C.; Thai, C. Tetrahedron Lett. 1999, 40, 9243.
2. Lycoramine as an Amaryllidaceae alkaloid was first isolated from Lycoris radiata by Kondo, Tomimura, and Ishiwata; see: (a) Kondo, H.; Tomimura, K.; Ishiwata, S. J. Pharm. Soc. Jpn. 1932, 52, 51. For the synthesis of lycoramine, see: (b) Barton, D. H. R. G.; Kirby, W. J. Chem. Soc. 1962, 806. (c) Hazama, N.; Irie, H.; Mizutani, T.; Shingu, T.; Takada, M.; Uyeo, S. J. Chem. Soc. C 1968, 2947. (d) Misaka, Y.; Mizutani, T.; Sekido, M.; Uyeo, S. J. Chem. Soc. C 1968, 2954. (e) Schultz, A. G.; Yee, Y. K.; Berger, M. H. J. Am. Chem. Soc. 1977, 99, 8065. (f) Martin, S. F.; Garrison, P. J. J. Org. Chem. 1981, 46, 3567. (g) Martin, S. F.; Garrison, P. J. J. Org. Chem. 1982, 47, 1513. (h) Sánchez, I. H.; Soria, J. J.; López, F. J.; Larraza, M. I.; Flores, H. J. J. Org. Chem. 1984, 49, 157. (i) Ackland, D. J.; Pinhey, J. T. J. Chem. Soc., Perkin Trans. 1 1987, 2695. (j) Parker, K. A.; Kim, H.-J. J. Org. Chem. 1992, 57, 752. (k) Ishizaki, M.; Ozaki, K.; Kanematsu, A.; Isoda, T.; Hoshino, O. J. Org. Chem. 1993, 58, 3877. (l) Kita, Y.; Arisawa, M.; Gyoten, M.; Nakajima, M.; Hamada, R.; Tohma, H.; Takada, T. J. Org. Chem. 1998, 63, 6625. (m) Gras, E.; Guillou, C.; Thai, C. Tetrahedron Lett. 1999, 40, 9243.
3. Lycoramine as an Amaryllidaceae alkaloid was first isolated from Lycoris radiata by Kondo, Tomimura, and Ishiwata; see: (a) Kondo, H.; Tomimura, K.; Ishiwata, S. J. Pharm. Soc. Jpn. 1932, 52, 51. For the synthesis of lycoramine, see: (b) Barton, D. H. R. G.; Kirby, W. J. Chem. Soc. 1962, 806. (c) Hazama, N.; Irie, H.; Mizutani, T.; Shingu, T.; Takada, M.; Uyeo, S. J. Chem. Soc. C 1968, 2947. (d) Misaka, Y.; Mizutani, T.; Sekido, M.; Uyeo, S. J. Chem. Soc. C 1968, 2954. (e) Schultz, A. G.; Yee, Y. K.; Berger, M. H. J. Am. Chem. Soc. 1977, 99, 8065. (f) Martin, S. F.; Garrison, P. J. J. Org. Chem. 1981, 46, 3567. (g) Martin, S. F.; Garrison, P. J. J. Org. Chem. 1982, 47, 1513. (h) Sánchez, I. H.; Soria, J. J.; López, F. J.; Larraza, M. I.; Flores, H. J. J. Org. Chem. 1984, 49, 157. (i) Ackland, D. J.; Pinhey, J. T. J. Chem. Soc., Perkin Trans. 1 1987, 2695. (j) Parker, K. A.; Kim, H.-J. J. Org. Chem. 1992, 57, 752. (k) Ishizaki, M.; Ozaki, K.; Kanematsu, A.; Isoda, T.; Hoshino, O. J. Org. Chem. 1993, 58, 3877. (l) Kita, Y.; Arisawa, M.; Gyoten, M.; Nakajima, M.; Hamada, R.; Tohma, H.; Takada, T. J. Org. Chem. 1998, 63, 6625. (m) Gras, E.; Guillou, C.; Thai, C. Tetrahedron Lett. 1999, 40, 9243.
4. Lycoramine as an Amaryllidaceae alkaloid was first isolated from Lycoris radiata by Kondo, Tomimura, and Ishiwata; see: (a) Kondo, H.; Tomimura, K.; Ishiwata, S. J. Pharm. Soc. Jpn. 1932, 52, 51. For the synthesis of lycoramine, see: (b) Barton, D. H. R. G.; Kirby, W. J. Chem. Soc. 1962, 806. (c) Hazama, N.; Irie, H.; Mizutani, T.; Shingu, T.; Takada, M.; Uyeo, S. J. Chem. Soc. C 1968, 2947. (d) Misaka, Y.; Mizutani, T.; Sekido, M.; Uyeo, S. J. Chem. Soc. C 1968, 2954. (e) Schultz, A. G.; Yee, Y. K.; Berger, M. H. J. Am. Chem. Soc. 1977, 99, 8065. (f) Martin, S. F.; Garrison, P. J. J. Org. Chem. 1981, 46, 3567. (g) Martin, S. F.; Garrison, P. J. J. Org. Chem. 1982, 47, 1513. (h) Sánchez, I. H.; Soria, J. J.; López, F. J.; Larraza, M. I.; Flores, H. J. J. Org. Chem. 1984, 49, 157. (i) Ackland, D. J.; Pinhey, J. T. J. Chem. Soc., Perkin Trans. 1 1987, 2695. (j) Parker, K. A.; Kim, H.-J. J. Org. Chem. 1992, 57, 752. (k) Ishizaki, M.; Ozaki, K.; Kanematsu, A.; Isoda, T.; Hoshino, O. J. Org. Chem. 1993, 58, 3877. (l) Kita, Y.; Arisawa, M.; Gyoten, M.; Nakajima, M.; Hamada, R.; Tohma, H.; Takada, T. J. Org. Chem. 1998, 63, 6625. (m) Gras, E.; Guillou, C.; Thai, C. Tetrahedron Lett. 1999, 40, 9243.
5. Lycoramine as an Amaryllidaceae alkaloid was first isolated from Lycoris radiata by Kondo, Tomimura, and Ishiwata; see: (a) Kondo, H.; Tomimura, K.; Ishiwata, S. J. Pharm. Soc. Jpn. 1932, 52, 51. For the synthesis of lycoramine, see: (b) Barton, D. H. R. G.; Kirby, W. J. Chem. Soc. 1962, 806. (c) Hazama, N.; Irie, H.; Mizutani, T.; Shingu, T.; Takada, M.; Uyeo, S. J. Chem. Soc. C 1968, 2947. (d) Misaka, Y.; Mizutani, T.; Sekido, M.; Uyeo, S. J. Chem. Soc. C 1968, 2954. (e) Schultz, A. G.; Yee, Y. K.; Berger, M. H. J. Am. Chem. Soc. 1977, 99, 8065. (f) Martin, S. F.; Garrison, P. J. J. Org. Chem. 1981, 46, 3567. (g) Martin, S. F.; Garrison, P. J. J. Org. Chem. 1982, 47, 1513. (h) Sánchez, I. H.; Soria, J. J.; López, F. J.; Larraza, M. I.; Flores, H. J. J. Org. Chem. 1984, 49, 157. (i) Ackland, D. J.; Pinhey, J. T. J. Chem. Soc., Perkin Trans. 1 1987, 2695. (j) Parker, K. A.; Kim, H.-J. J. Org. Chem. 1992, 57, 752. (k) Ishizaki, M.; Ozaki, K.; Kanematsu, A.; Isoda, T.; Hoshino, O. J. Org. Chem. 1993, 58, 3877. (l) Kita, Y.; Arisawa, M.; Gyoten, M.; Nakajima, M.; Hamada, R.; Tohma, H.; Takada, T. J. Org. Chem. 1998, 63, 6625. (m) Gras, E.; Guillou, C.; Thai, C. Tetrahedron Lett. 1999, 40, 9243.
6. Lycoramine as an Amaryllidaceae alkaloid was first isolated from Lycoris radiata by Kondo, Tomimura, and Ishiwata; see: (a) Kondo, H.; Tomimura, K.; Ishiwata, S. J. Pharm. Soc. Jpn. 1932, 52, 51. For the synthesis of lycoramine, see: (b) Barton, D. H. R. G.; Kirby, W. J. Chem. Soc. 1962, 806. (c) Hazama, N.; Irie, H.; Mizutani, T.; Shingu, T.; Takada, M.; Uyeo, S. J. Chem. Soc. C 1968, 2947. (d) Misaka, Y.; Mizutani, T.; Sekido, M.; Uyeo, S. J. Chem. Soc. C 1968, 2954. (e) Schultz, A. G.; Yee, Y. K.; Berger, M. H. J. Am. Chem. Soc. 1977, 99, 8065. (f) Martin, S. F.; Garrison, P. J. J. Org. Chem. 1981, 46, 3567. (g) Martin, S. F.; Garrison, P. J. J. Org. Chem. 1982, 47, 1513. (h) Sánchez, I. H.; Soria, J. J.; López, F. J.; Larraza, M. I.; Flores, H. J. J. Org. Chem. 1984, 49, 157. (i) Ackland, D. J.; Pinhey, J. T. J. Chem. Soc., Perkin Trans. 1 1987, 2695. (j) Parker, K. A.; Kim, H.-J. J. Org. Chem. 1992, 57, 752. (k) Ishizaki, M.; Ozaki, K.; Kanematsu, A.; Isoda, T.; Hoshino, O. J. Org. Chem. 1993, 58, 3877. (l) Kita, Y.; Arisawa, M.; Gyoten, M.; Nakajima, M.; Hamada, R.; Tohma, H.; Takada, T. J. Org. Chem. 1998, 63, 6625. (m) Gras, E.; Guillou, C.; Thai, C. Tetrahedron Lett. 1999, 40, 9243.
7. Lycoramine as an Amaryllidaceae alkaloid was first isolated from Lycoris radiata by Kondo, Tomimura, and Ishiwata; see: (a) Kondo, H.; Tomimura, K.; Ishiwata, S. J. Pharm. Soc. Jpn. 1932, 52, 51. For the synthesis of lycoramine, see: (b) Barton, D. H. R. G.; Kirby, W. J. Chem. Soc. 1962, 806. (c) Hazama, N.; Irie, H.; Mizutani, T.; Shingu, T.; Takada, M.; Uyeo, S. J. Chem. Soc. C 1968, 2947. (d) Misaka, Y.; Mizutani, T.; Sekido, M.; Uyeo, S. J. Chem. Soc. C 1968, 2954. (e) Schultz, A. G.; Yee, Y. K.; Berger, M. H. J. Am. Chem. Soc. 1977, 99, 8065. (f) Martin, S. F.; Garrison, P. J. J. Org. Chem. 1981, 46, 3567. (g) Martin, S. F.; Garrison, P. J. J. Org. Chem. 1982, 47, 1513. (h) Sánchez, I. H.; Soria, J. J.; López, F. J.; Larraza, M. I.; Flores, H. J. J. Org. Chem. 1984, 49, 157. (i) Ackland, D. J.; Pinhey, J. T. J. Chem. Soc., Perkin Trans. 1 1987, 2695. (j) Parker, K. A.; Kim, H.-J. J. Org. Chem. 1992, 57, 752. (k) Ishizaki, M.; Ozaki, K.; Kanematsu, A.; Isoda, T.; Hoshino, O. J. Org. Chem. 1993, 58, 3877. (l) Kita, Y.; Arisawa, M.; Gyoten, M.; Nakajima, M.; Hamada, R.; Tohma, H.; Takada, T. J. Org. Chem. 1998, 63, 6625. (m) Gras, E.; Guillou, C.; Thai, C. Tetrahedron Lett. 1999, 40, 9243.
8. Lycoramine as an Amaryllidaceae alkaloid was first isolated from Lycoris radiata by Kondo, Tomimura, and Ishiwata; see: (a) Kondo, H.; Tomimura, K.; Ishiwata, S. J. Pharm. Soc. Jpn. 1932, 52, 51. For the synthesis of lycoramine, see: (b) Barton, D. H. R. G.; Kirby, W. J. Chem. Soc. 1962, 806. (c) Hazama, N.; Irie, H.; Mizutani, T.; Shingu, T.; Takada, M.; Uyeo, S. J. Chem. Soc. C 1968, 2947. (d) Misaka, Y.; Mizutani, T.; Sekido, M.; Uyeo, S. J. Chem. Soc. C 1968, 2954. (e) Schultz, A. G.; Yee, Y. K.; Berger, M. H. J. Am. Chem. Soc. 1977, 99, 8065. (f) Martin, S. F.; Garrison, P. J. J. Org. Chem. 1981, 46, 3567. (g) Martin, S. F.; Garrison, P. J. J. Org. Chem. 1982, 47, 1513. (h) Sánchez, I. H.; Soria, J. J.; López, F. J.; Larraza, M. I.; Flores, H. J. J. Org. Chem. 1984, 49, 157. (i) Ackland, D. J.; Pinhey, J. T. J. Chem. Soc., Perkin Trans. 1 1987, 2695. (j) Parker, K. A.; Kim, H.-J. J. Org. Chem. 1992, 57, 752. (k) Ishizaki, M.; Ozaki, K.; Kanematsu, A.; Isoda, T.; Hoshino, O. J. Org. Chem. 1993, 58, 3877. (l) Kita, Y.; Arisawa, M.; Gyoten, M.; Nakajima, M.; Hamada, R.; Tohma, H.; Takada, T. J. Org. Chem. 1998, 63, 6625. (m) Gras, E.; Guillou, C.; Thai, C. Tetrahedron Lett. 1999, 40, 9243.
9. Lycoramine as an Amaryllidaceae alkaloid was first isolated from Lycoris radiata by Kondo, Tomimura, and Ishiwata; see: (a) Kondo, H.; Tomimura, K.; Ishiwata, S. J. Pharm. Soc. Jpn. 1932, 52, 51. For the synthesis of lycoramine, see: (b) Barton, D. H. R. G.; Kirby, W. J. Chem. Soc. 1962, 806. (c) Hazama, N.; Irie, H.; Mizutani, T.; Shingu, T.; Takada, M.; Uyeo, S. J. Chem. Soc. C 1968, 2947. (d) Misaka, Y.; Mizutani, T.; Sekido, M.; Uyeo, S. J. Chem. Soc. C 1968, 2954. (e) Schultz, A. G.; Yee, Y. K.; Berger, M. H. J. Am. Chem. Soc. 1977, 99, 8065. (f) Martin, S. F.; Garrison, P. J. J. Org. Chem. 1981, 46, 3567. (g) Martin, S. F.; Garrison, P. J. J. Org. Chem. 1982, 47, 1513. (h) Sánchez, I. H.; Soria, J. J.; López, F. J.; Larraza, M. I.; Flores, H. J. J. Org. Chem. 1984, 49, 157. (i) Ackland, D. J.; Pinhey, J. T. J. Chem. Soc., Perkin Trans. 1 1987, 2695. (j) Parker, K. A.; Kim, H.-J. J. Org. Chem. 1992, 57, 752. (k) Ishizaki, M.; Ozaki, K.; Kanematsu, A.; Isoda, T.; Hoshino, O. J. Org. Chem. 1993, 58, 3877. (l) Kita, Y.; Arisawa, M.; Gyoten, M.; Nakajima, M.; Hamada, R.; Tohma, H.; Takada, T. J. Org. Chem. 1998, 63, 6625. (m) Gras, E.; Guillou, C.; Thai, C. Tetrahedron Lett. 1999, 40, 9243.
10. Lycoramine as an Amaryllidaceae alkaloid was first isolated from Lycoris radiata by Kondo, Tomimura, and Ishiwata; see: (a) Kondo, H.; Tomimura, K.; Ishiwata, S. J. Pharm. Soc. Jpn. 1932, 52, 51. For the synthesis of lycoramine, see: (b) Barton, D. H. R. G.; Kirby, W. J. Chem. Soc. 1962, 806. (c) Hazama, N.; Irie, H.; Mizutani, T.; Shingu, T.; Takada, M.; Uyeo, S. J. Chem. Soc. C 1968, 2947. (d) Misaka, Y.; Mizutani, T.; Sekido, M.; Uyeo, S. J. Chem. Soc. C 1968, 2954. (e) Schultz, A. G.; Yee, Y. K.; Berger, M. H. J. Am. Chem. Soc. 1977, 99, 8065. (f) Martin, S. F.; Garrison, P. J. J. Org. Chem. 1981, 46, 3567. (g) Martin, S. F.; Garrison, P. J. J. Org. Chem. 1982, 47, 1513. (h) Sánchez, I. H.; Soria, J. J.; López, F. J.; Larraza, M. I.; Flores, H. J. J. Org. Chem. 1984, 49, 157. (i) Ackland, D. J.; Pinhey, J. T. J. Chem. Soc., Perkin Trans. 1 1987, 2695. (j) Parker, K. A.; Kim, H.-J. J. Org. Chem. 1992, 57, 752. (k) Ishizaki, M.; Ozaki, K.; Kanematsu, A.; Isoda, T.; Hoshino, O. J. Org. Chem. 1993, 58, 3877. (l) Kita, Y.; Arisawa, M.; Gyoten, M.; Nakajima, M.; Hamada, R.; Tohma, H.; Takada, T. J. Org. Chem. 1998, 63, 6625. (m) Gras, E.; Guillou, C.; Thai, C. Tetrahedron Lett. 1999, 40, 9243.
11. Lycoramine as an Amaryllidaceae alkaloid was first isolated from Lycoris radiata by Kondo, Tomimura, and Ishiwata; see: (a) Kondo, H.; Tomimura, K.; Ishiwata, S. J. Pharm. Soc. Jpn. 1932, 52, 51. For the synthesis of lycoramine, see: (b) Barton, D. H. R. G.; Kirby, W. J. Chem. Soc. 1962, 806. (c) Hazama, N.; Irie, H.; Mizutani, T.; Shingu, T.; Takada, M.; Uyeo, S. J. Chem. Soc. C 1968, 2947. (d) Misaka, Y.; Mizutani, T.; Sekido, M.; Uyeo, S. J. Chem. Soc. C 1968, 2954. (e) Schultz, A. G.; Yee, Y. K.; Berger, M. H. J. Am. Chem. Soc. 1977, 99, 8065. (f) Martin, S. F.; Garrison, P. J. J. Org. Chem. 1981, 46, 3567. (g) Martin, S. F.; Garrison, P. J. J. Org. Chem. 1982, 47, 1513. (h) Sánchez, I. H.; Soria, J. J.; López, F. J.; Larraza, M. I.; Flores, H. J. J. Org. Chem. 1984, 49, 157. (i) Ackland, D. J.; Pinhey, J. T. J. Chem. Soc., Perkin Trans. 1 1987, 2695. (j) Parker, K. A.; Kim, H.-J. J. Org. Chem. 1992, 57, 752. (k) Ishizaki, M.; Ozaki, K.; Kanematsu, A.; Isoda, T.; Hoshino, O. J. Org. Chem. 1993, 58, 3877. (l) Kita, Y.; Arisawa, M.; Gyoten, M.; Nakajima, M.; Hamada, R.; Tohma, H.; Takada, T. J. Org. Chem. 1998, 63, 6625. (m) Gras, E.; Guillou, C.; Thai, C. Tetrahedron Lett. 1999, 40, 9243.
12. Lycoramine as an Amaryllidaceae alkaloid was first isolated from Lycoris radiata by Kondo, Tomimura, and Ishiwata; see: (a) Kondo, H.; Tomimura, K.; Ishiwata, S. J. Pharm. Soc. Jpn. 1932, 52, 51. For the synthesis of lycoramine, see: (b) Barton, D. H. R. G.; Kirby, W. J. Chem. Soc. 1962, 806. (c) Hazama, N.; Irie, H.; Mizutani, T.; Shingu, T.; Takada, M.; Uyeo, S. J. Chem. Soc. C 1968, 2947. (d) Misaka, Y.; Mizutani, T.; Sekido, M.; Uyeo, S. J. Chem. Soc. C 1968, 2954. (e) Schultz, A. G.; Yee, Y. K.; Berger, M. H. J. Am. Chem. Soc. 1977, 99, 8065. (f) Martin, S. F.; Garrison, P. J. J. Org. Chem. 1981, 46, 3567. (g) Martin, S. F.; Garrison, P. J. J. Org. Chem. 1982, 47, 1513. (h) Sánchez, I. H.; Soria, J. J.; López, F. J.; Larraza, M. I.; Flores, H. J. J. Org. Chem. 1984, 49, 157. (i) Ackland, D. J.; Pinhey, J. T. J. Chem. Soc., Perkin Trans. 1 1987, 2695. (j) Parker, K. A.; Kim, H.-J. J. Org. Chem. 1992, 57, 752. (k) Ishizaki, M.; Ozaki, K.; Kanematsu, A.; Isoda, T.; Hoshino, O. J. Org. Chem. 1993, 58, 3877. (l) Kita, Y.; Arisawa, M.; Gyoten, M.; Nakajima, M.; Hamada, R.; Tohma, H.; Takada, T. J. Org. Chem. 1998, 63, 6625. (m) Gras, E.; Guillou, C.; Thai, C. Tetrahedron Lett. 1999, 40, 9243.
13. Lycoramine as an Amaryllidaceae alkaloid was first isolated from Lycoris radiata by Kondo, Tomimura, and Ishiwata; see: (a) Kondo, H.; Tomimura, K.; Ishiwata, S. J. Pharm. Soc. Jpn. 1932, 52, 51. For the synthesis of lycoramine, see: (b) Barton, D. H. R. G.; Kirby, W. J. Chem. Soc. 1962, 806. (c) Hazama, N.; Irie, H.; Mizutani, T.; Shingu, T.; Takada, M.; Uyeo, S. J. Chem. Soc. C 1968, 2947. (d) Misaka, Y.; Mizutani, T.; Sekido, M.; Uyeo, S. J. Chem. Soc. C 1968, 2954. (e) Schultz, A. G.; Yee, Y. K.; Berger, M. H. J. Am. Chem. Soc. 1977, 99, 8065. (f) Martin, S. F.; Garrison, P. J. J. Org. Chem. 1981, 46, 3567. (g) Martin, S. F.; Garrison, P. J. J. Org. Chem. 1982, 47, 1513. (h) Sánchez, I. H.; Soria, J. J.; López, F. J.; Larraza, M. I.; Flores, H. J. J. Org. Chem. 1984, 49, 157. (i) Ackland, D. J.; Pinhey, J. T. J. Chem. Soc., Perkin Trans. 1 1987, 2695. (j) Parker, K. A.; Kim, H.-J. J. Org. Chem. 1992, 57, 752. (k) Ishizaki, M.; Ozaki, K.; Kanematsu, A.; Isoda, T.; Hoshino, O. J. Org. Chem. 1993, 58, 3877. (l) Kita, Y.; Arisawa, M.; Gyoten, M.; Nakajima, M.; Hamada, R.; Tohma, H.; Takada, T. J. Org. Chem. 1998, 63, 6625. (m) Gras, E.; Guillou, C.; Thai, C. Tetrahedron Lett. 1999, 40, 9243.
14. For the synthesis of galanthamine by biomimetic oxidation coupling, see: (a) Kodama, S.; Hamashima, Y.; Nishide, K.; Node, M. Angew. Chem., Int. Ed. 2004, 43, 2659 and references therein. For its synthesis by Heck reaction, see: (b) Trost, B. M.; Tang, W. Angew. Chem. Int. Ed. 2002, 41, 2795 and references therein.
15. For the synthesis of galanthamine by biomimetic oxidation coupling, see: (a) Kodama, S.; Hamashima, Y.; Nishide, K.; Node, M. Angew. Chem., Int. Ed. 2004, 43, 2659 and references therein. For its synthesis by Heck reaction, see: (b) Trost, B. M.; Tang, W. Angew. Chem. Int. Ed. 2002, 41, 2795 and references therein.
16. For the synthesis of narwedine, see refs 1b,f,1 and 2b,k and also see: (a) Holten, R. A.; Sibi, M. P.; Murphy, W. S. J. Am. Chem. Soc. 1988, 110, 314. (b) Chaplin, D. A.; Fraser, N.; Tiffin, P. D. Tetrahedron Lett. 1997, 38, 7931.
17. For the synthesis of narwedine, see refs 1b,f,1 and 2b,k and also see: (a) Holten, R. A.; Sibi, M. P.; Murphy, W. S. J. Am. Chem. Soc. 1988, 110, 314. (b) Chaplin, D. A.; Fraser, N.; Tiffin, P. D. Tetrahedron Lett. 1997, 38, 7931.
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19. See also ref 11 and references therein.
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23. For the application of Pictet - Spengler reaction to the formation of benzazepine ring, see ref 1k and also see: (a) Kametani, T.; Terui, T.; Ogino, T.; Fukumoto, K. J. Chem. Soc. C 1969, 874. (b) Wittekind, R. R.; Lazarus, S. J. Heterocycl. Chem. 1971, 8, 495.
24. For the application of Pictet - Spengler reaction to the formation of benzazepine ring, see ref 1k and also see: (a) Kametani, T.; Terui, T.; Ogino, T.; Fukumoto, K. J. Chem. Soc. C 1969, 874. (b) Wittekind, R. R.; Lazarus, S. J. Heterocycl. Chem. 1971, 8, 495.
25. Song, Z.-L.; Wang, B.-M.; Tu, Y.-Q.; Fan, C.-A.; Zhang, S.-Y. Org. Lett. 2003, 5, 2319.
26. For its relative stereochemistry confirmed by 1D NOSEY spectrum of the further cyclization product 9, see the Supporting Information.
27. Unpublished result, and see Scheme 1 of the Supporting Information.
28. (a) Moriarty, K. J.; Shen, C-C.; Paquette, L. A. Synlett 1990, 263.
29. (b) Paquette, L. A.; Owen, D. R.; Bibart, R. T.; Seekamp, C. K.; Kahane, A. L.; Lanter, J. C.; Corral, M. A. J. Org. Chem. 2001, 66, 2828.
30. (c) Hurley, P. B.; Dake, G. R. Synlett 2003, 2131.
31. See Table 1 of the Supporting Information.
32. Supported experiments; see Table 2 of the Supporting Information.
33. See Table 3 of the Supporting Information.
34. DBU as a hindered organic base is usually used for the dehydrohalogenation of alkyl halides; see: Larock, R. C. In Comprehensive Organic Transformation; 2nd ed.; Wiley: New York, 1999; p 258.
35. Few effectively selective deprotections of phenolic TBS ethers bearing electron-donating group without affecting aliphatic TBS moiety have been reported; see: Oyama, K.-I.; Kondo, T. Org. Lett. 2003, 5, 209. For a possible mechanism in this DBU-induced transformation, see Scheme 2 of the Supporting Information.
36. For example, see: (a) Levine, S. G. J. Am. Chem. Soc. 1958, 80, 6150. (b) Ohtani, M.; Matsuura, T.; Watanabe, F.; Narisada, M. J. Org. Chem. 1991, 56, 2122.
37. For example, see: (a) Levine, S. G. J. Am. Chem. Soc. 1958, 80, 6150. (b) Ohtani, M.; Matsuura, T.; Watanabe, F.; Narisada, M. J. Org. Chem. 1991, 56, 2122.
38. Corey, E. J.; Narasaka, K.; Shibasaki, M. J. Am. Chem. Soc. 1976, 98, 6417.
39. Markó, I. E.; Mekhalfia, A. Tetrahedron Lett. 1990, 31, 7237.