Stereoselective synthesis of fused bicyclic β-lactams through radical cyclization of enyne-2-azetidinones

Journal of Organic Chemistry

Volumn 64, Issue 15, 1999, Pages 5377-5387

  Alcaide, Benito ^a   Rodríguez Campos, Ignacio M ^a   Rodríguez López, Julián ^a   Rodríguez Vicente, Alberto ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM;

ARTICLE; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; TECHNIQUE;

EID: 0345363299     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9823994     Document Type: Article

References (131)

1. For a preliminary communication describing part of this work, see: Alcaide, B.; Benito, J. L.; Rodríguez-Campos, I. M.; Rodríguez-López, J.; Rodríguez-Vicente, A.; Sierra, M. A.; García-Granda, S.; Gutíerrez-Rodríguez, A. Tetrahedron: Asymmetry 1996, 6, 1055.
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15. 3SnH: (a) Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418. (b) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. (c) Janardhanam, S.; Balakumar, A.; Rajagopalan, K. J. Chem. Soc., Perkin Trans, 1 1994, 551. (d) Janardhanam, S.; Shanmugam, P.; Rajagopalan, K. J. Org. Chem. 1993, 58, 7782. (e) Hanessian, S.; Léger, R. J. Am. Chem. Soc. 1992, 114, 3115. (f) Enholm, E. J.; Kinter, K. S. J. Am. Chem. Soc. 1991, 113, 7784. (g) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc. 1991, 113, 6268. (h) Yang, Z.-Y.; Burton, D. J. J. Org. Chem. 1991, 56, 5125. (i) Stork, G.; Reynolds, M. E. J. Am. Chem. Soc. 1988, 110, 6911. Cyclizations using silicon hydrides: (j) Kopping, B.; Chatgilialoglu, C.; Zehnder, M.; Giese, B. J. Org. Chem. 1992, 57, 3994. Cyclizations using sulfur- and phosphorus-centered radicals: (k) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron 1994, 50, 13533. (l) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1215. (m) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1219. (n) Chuang, C.-P. Tetrahedron Lett. 1992, 33, 6311. (o) Serra, A. C.; da Silva Correa, C. M. M.; do Vale, M. L. C. Tetrahedron 1991, 47, 9463. (p) De Riggi, I.; Surzur, J.-M.; Bertrand, M. P.; Archavlis, A.; Faure, R. Tetrahedron 1990, 46, 5285. (q) Chuang, C.-P. Synlett 1990, 527. (r) Broka, C. A.; Reichert, D. E. C. Tetrahedron Lett. 1987, 28, 1503. (s) Padwa, A. Nimmesgern, H.; Wong, G. S. K. J. Org. Chem. 1985, 50, 5620.
16. 3SnH: (a) Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418. (b) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. (c) Janardhanam, S.; Balakumar, A.; Rajagopalan, K. J. Chem. Soc., Perkin Trans, 1 1994, 551. (d) Janardhanam, S.; Shanmugam, P.; Rajagopalan, K. J. Org. Chem. 1993, 58, 7782. (e) Hanessian, S.; Léger, R. J. Am. Chem. Soc. 1992, 114, 3115. (f) Enholm, E. J.; Kinter, K. S. J. Am. Chem. Soc. 1991, 113, 7784. (g) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc. 1991, 113, 6268. (h) Yang, Z.-Y.; Burton, D. J. J. Org. Chem. 1991, 56, 5125. (i) Stork, G.; Reynolds, M. E. J. Am. Chem. Soc. 1988, 110, 6911. Cyclizations using silicon hydrides: (j) Kopping, B.; Chatgilialoglu, C.; Zehnder, M.; Giese, B. J. Org. Chem. 1992, 57, 3994. Cyclizations using sulfur- and phosphorus-centered radicals: (k) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron 1994, 50, 13533. (l) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1215. (m) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1219. (n) Chuang, C.-P. Tetrahedron Lett. 1992, 33, 6311. (o) Serra, A. C.; da Silva Correa, C. M. M.; do Vale, M. L. C. Tetrahedron 1991, 47, 9463. (p) De Riggi, I.; Surzur, J.-M.; Bertrand, M. P.; Archavlis, A.; Faure, R. Tetrahedron 1990, 46, 5285. (q) Chuang, C.-P. Synlett 1990, 527. (r) Broka, C. A.; Reichert, D. E. C. Tetrahedron Lett. 1987, 28, 1503. (s) Padwa, A. Nimmesgern, H.; Wong, G. S. K. J. Org. Chem. 1985, 50, 5620.
17. 3SnH: (a) Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418. (b) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. (c) Janardhanam, S.; Balakumar, A.; Rajagopalan, K. J. Chem. Soc., Perkin Trans, 1 1994, 551. (d) Janardhanam, S.; Shanmugam, P.; Rajagopalan, K. J. Org. Chem. 1993, 58, 7782. (e) Hanessian, S.; Léger, R. J. Am. Chem. Soc. 1992, 114, 3115. (f) Enholm, E. J.; Kinter, K. S. J. Am. Chem. Soc. 1991, 113, 7784. (g) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc. 1991, 113, 6268. (h) Yang, Z.-Y.; Burton, D. J. J. Org. Chem. 1991, 56, 5125. (i) Stork, G.; Reynolds, M. E. J. Am. Chem. Soc. 1988, 110, 6911. Cyclizations using silicon hydrides: (j) Kopping, B.; Chatgilialoglu, C.; Zehnder, M.; Giese, B. J. Org. Chem. 1992, 57, 3994. Cyclizations using sulfur- and phosphorus-centered radicals: (k) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron 1994, 50, 13533. (l) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1215. (m) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1219. (n) Chuang, C.-P. Tetrahedron Lett. 1992, 33, 6311. (o) Serra, A. C.; da Silva Correa, C. M. M.; do Vale, M. L. C. Tetrahedron 1991, 47, 9463. (p) De Riggi, I.; Surzur, J.-M.; Bertrand, M. P.; Archavlis, A.; Faure, R. Tetrahedron 1990, 46, 5285. (q) Chuang, C.-P. Synlett 1990, 527. (r) Broka, C. A.; Reichert, D. E. C. Tetrahedron Lett. 1987, 28, 1503. (s) Padwa, A. Nimmesgern, H.; Wong, G. S. K. J. Org. Chem. 1985, 50, 5620.
18. 3SnH: (a) Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418. (b) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. (c) Janardhanam, S.; Balakumar, A.; Rajagopalan, K. J. Chem. Soc., Perkin Trans, 1 1994, 551. (d) Janardhanam, S.; Shanmugam, P.; Rajagopalan, K. J. Org. Chem. 1993, 58, 7782. (e) Hanessian, S.; Léger, R. J. Am. Chem. Soc. 1992, 114, 3115. (f) Enholm, E. J.; Kinter, K. S. J. Am. Chem. Soc. 1991, 113, 7784. (g) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc. 1991, 113, 6268. (h) Yang, Z.-Y.; Burton, D. J. J. Org. Chem. 1991, 56, 5125. (i) Stork, G.; Reynolds, M. E. J. Am. Chem. Soc. 1988, 110, 6911. Cyclizations using silicon hydrides: (j) Kopping, B.; Chatgilialoglu, C.; Zehnder, M.; Giese, B. J. Org. Chem. 1992, 57, 3994. Cyclizations using sulfur- and phosphorus-centered radicals: (k) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron 1994, 50, 13533. (l) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1215. (m) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1219. (n) Chuang, C.-P. Tetrahedron Lett. 1992, 33, 6311. (o) Serra, A. C.; da Silva Correa, C. M. M.; do Vale, M. L. C. Tetrahedron 1991, 47, 9463. (p) De Riggi, I.; Surzur, J.-M.; Bertrand, M. P.; Archavlis, A.; Faure, R. Tetrahedron 1990, 46, 5285. (q) Chuang, C.-P. Synlett 1990, 527. (r) Broka, C. A.; Reichert, D. E. C. Tetrahedron Lett. 1987, 28, 1503. (s) Padwa, A. Nimmesgern, H.; Wong, G. S. K. J. Org. Chem. 1985, 50, 5620.
19. 3SnH: (a) Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418. (b) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. (c) Janardhanam, S.; Balakumar, A.; Rajagopalan, K. J. Chem. Soc., Perkin Trans, 1 1994, 551. (d) Janardhanam, S.; Shanmugam, P.; Rajagopalan, K. J. Org. Chem. 1993, 58, 7782. (e) Hanessian, S.; Léger, R. J. Am. Chem. Soc. 1992, 114, 3115. (f) Enholm, E. J.; Kinter, K. S. J. Am. Chem. Soc. 1991, 113, 7784. (g) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc. 1991, 113, 6268. (h) Yang, Z.-Y.; Burton, D. J. J. Org. Chem. 1991, 56, 5125. (i) Stork, G.; Reynolds, M. E. J. Am. Chem. Soc. 1988, 110, 6911. Cyclizations using silicon hydrides: (j) Kopping, B.; Chatgilialoglu, C.; Zehnder, M.; Giese, B. J. Org. Chem. 1992, 57, 3994. Cyclizations using sulfur- and phosphorus-centered radicals: (k) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron 1994, 50, 13533. (l) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1215. (m) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1219. (n) Chuang, C.-P. Tetrahedron Lett. 1992, 33, 6311. (o) Serra, A. C.; da Silva Correa, C. M. M.; do Vale, M. L. C. Tetrahedron 1991, 47, 9463. (p) De Riggi, I.; Surzur, J.-M.; Bertrand, M. P.; Archavlis, A.; Faure, R. Tetrahedron 1990, 46, 5285. (q) Chuang, C.-P. Synlett 1990, 527. (r) Broka, C. A.; Reichert, D. E. C. Tetrahedron Lett. 1987, 28, 1503. (s) Padwa, A. Nimmesgern, H.; Wong, G. S. K. J. Org. Chem. 1985, 50, 5620.
20. 3SnH: (a) Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418. (b) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. (c) Janardhanam, S.; Balakumar, A.; Rajagopalan, K. J. Chem. Soc., Perkin Trans, 1 1994, 551. (d) Janardhanam, S.; Shanmugam, P.; Rajagopalan, K. J. Org. Chem. 1993, 58, 7782. (e) Hanessian, S.; Léger, R. J. Am. Chem. Soc. 1992, 114, 3115. (f) Enholm, E. J.; Kinter, K. S. J. Am. Chem. Soc. 1991, 113, 7784. (g) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc. 1991, 113, 6268. (h) Yang, Z.-Y.; Burton, D. J. J. Org. Chem. 1991, 56, 5125. (i) Stork, G.; Reynolds, M. E. J. Am. Chem. Soc. 1988, 110, 6911. Cyclizations using silicon hydrides: (j) Kopping, B.; Chatgilialoglu, C.; Zehnder, M.; Giese, B. J. Org. Chem. 1992, 57, 3994. Cyclizations using sulfur- and phosphorus-centered radicals: (k) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron 1994, 50, 13533. (l) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1215. (m) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1219. (n) Chuang, C.-P. Tetrahedron Lett. 1992, 33, 6311. (o) Serra, A. C.; da Silva Correa, C. M. M.; do Vale, M. L. C. Tetrahedron 1991, 47, 9463. (p) De Riggi, I.; Surzur, J.-M.; Bertrand, M. P.; Archavlis, A.; Faure, R. Tetrahedron 1990, 46, 5285. (q) Chuang, C.-P. Synlett 1990, 527. (r) Broka, C. A.; Reichert, D. E. C. Tetrahedron Lett. 1987, 28, 1503. (s) Padwa, A. Nimmesgern, H.; Wong, G. S. K. J. Org. Chem. 1985, 50, 5620.
21. 3SnH: (a) Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418. (b) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. (c) Janardhanam, S.; Balakumar, A.; Rajagopalan, K. J. Chem. Soc., Perkin Trans, 1 1994, 551. (d) Janardhanam, S.; Shanmugam, P.; Rajagopalan, K. J. Org. Chem. 1993, 58, 7782. (e) Hanessian, S.; Léger, R. J. Am. Chem. Soc. 1992, 114, 3115. (f) Enholm, E. J.; Kinter, K. S. J. Am. Chem. Soc. 1991, 113, 7784. (g) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc. 1991, 113, 6268. (h) Yang, Z.-Y.; Burton, D. J. J. Org. Chem. 1991, 56, 5125. (i) Stork, G.; Reynolds, M. E. J. Am. Chem. Soc. 1988, 110, 6911. Cyclizations using silicon hydrides: (j) Kopping, B.; Chatgilialoglu, C.; Zehnder, M.; Giese, B. J. Org. Chem. 1992, 57, 3994. Cyclizations using sulfur- and phosphorus-centered radicals: (k) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron 1994, 50, 13533. (l) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1215. (m) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1219. (n) Chuang, C.-P. Tetrahedron Lett. 1992, 33, 6311. (o) Serra, A. C.; da Silva Correa, C. M. M.; do Vale, M. L. C. Tetrahedron 1991, 47, 9463. (p) De Riggi, I.; Surzur, J.-M.; Bertrand, M. P.; Archavlis, A.; Faure, R. Tetrahedron 1990, 46, 5285. (q) Chuang, C.-P. Synlett 1990, 527. (r) Broka, C. A.; Reichert, D. E. C. Tetrahedron Lett. 1987, 28, 1503. (s) Padwa, A. Nimmesgern, H.; Wong, G. S. K. J. Org. Chem. 1985, 50, 5620.
22. 3SnH: (a) Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418. (b) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. (c) Janardhanam, S.; Balakumar, A.; Rajagopalan, K. J. Chem. Soc., Perkin Trans, 1 1994, 551. (d) Janardhanam, S.; Shanmugam, P.; Rajagopalan, K. J. Org. Chem. 1993, 58, 7782. (e) Hanessian, S.; Léger, R. J. Am. Chem. Soc. 1992, 114, 3115. (f) Enholm, E. J.; Kinter, K. S. J. Am. Chem. Soc. 1991, 113, 7784. (g) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc. 1991, 113, 6268. (h) Yang, Z.-Y.; Burton, D. J. J. Org. Chem. 1991, 56, 5125. (i) Stork, G.; Reynolds, M. E. J. Am. Chem. Soc. 1988, 110, 6911. Cyclizations using silicon hydrides: (j) Kopping, B.; Chatgilialoglu, C.; Zehnder, M.; Giese, B. J. Org. Chem. 1992, 57, 3994. Cyclizations using sulfur- and phosphorus-centered radicals: (k) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron 1994, 50, 13533. (l) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1215. (m) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1219. (n) Chuang, C.-P. Tetrahedron Lett. 1992, 33, 6311. (o) Serra, A. C.; da Silva Correa, C. M. M.; do Vale, M. L. C. Tetrahedron 1991, 47, 9463. (p) De Riggi, I.; Surzur, J.-M.; Bertrand, M. P.; Archavlis, A.; Faure, R. Tetrahedron 1990, 46, 5285. (q) Chuang, C.-P. Synlett 1990, 527. (r) Broka, C. A.; Reichert, D. E. C. Tetrahedron Lett. 1987, 28, 1503. (s) Padwa, A. Nimmesgern, H.; Wong, G. S. K. J. Org. Chem. 1985, 50, 5620.
23. 3SnH: (a) Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418. (b) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. (c) Janardhanam, S.; Balakumar, A.; Rajagopalan, K. J. Chem. Soc., Perkin Trans, 1 1994, 551. (d) Janardhanam, S.; Shanmugam, P.; Rajagopalan, K. J. Org. Chem. 1993, 58, 7782. (e) Hanessian, S.; Léger, R. J. Am. Chem. Soc. 1992, 114, 3115. (f) Enholm, E. J.; Kinter, K. S. J. Am. Chem. Soc. 1991, 113, 7784. (g) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc. 1991, 113, 6268. (h) Yang, Z.-Y.; Burton, D. J. J. Org. Chem. 1991, 56, 5125. (i) Stork, G.; Reynolds, M. E. J. Am. Chem. Soc. 1988, 110, 6911. Cyclizations using silicon hydrides: (j) Kopping, B.; Chatgilialoglu, C.; Zehnder, M.; Giese, B. J. Org. Chem. 1992, 57, 3994. Cyclizations using sulfur- and phosphorus-centered radicals: (k) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron 1994, 50, 13533. (l) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1215. (m) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1219. (n) Chuang, C.-P. Tetrahedron Lett. 1992, 33, 6311. (o) Serra, A. C.; da Silva Correa, C. M. M.; do Vale, M. L. C. Tetrahedron 1991, 47, 9463. (p) De Riggi, I.; Surzur, J.-M.; Bertrand, M. P.; Archavlis, A.; Faure, R. Tetrahedron 1990, 46, 5285. (q) Chuang, C.-P. Synlett 1990, 527. (r) Broka, C. A.; Reichert, D. E. C. Tetrahedron Lett. 1987, 28, 1503. (s) Padwa, A. Nimmesgern, H.; Wong, G. S. K. J. Org. Chem. 1985, 50, 5620.
24. 3SnH: (a) Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418. (b) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. (c) Janardhanam, S.; Balakumar, A.; Rajagopalan, K. J. Chem. Soc., Perkin Trans, 1 1994, 551. (d) Janardhanam, S.; Shanmugam, P.; Rajagopalan, K. J. Org. Chem. 1993, 58, 7782. (e) Hanessian, S.; Léger, R. J. Am. Chem. Soc. 1992, 114, 3115. (f) Enholm, E. J.; Kinter, K. S. J. Am. Chem. Soc. 1991, 113, 7784. (g) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc. 1991, 113, 6268. (h) Yang, Z.-Y.; Burton, D. J. J. Org. Chem. 1991, 56, 5125. (i) Stork, G.; Reynolds, M. E. J. Am. Chem. Soc. 1988, 110, 6911. Cyclizations using silicon hydrides: (j) Kopping, B.; Chatgilialoglu, C.; Zehnder, M.; Giese, B. J. Org. Chem. 1992, 57, 3994. Cyclizations using sulfur- and phosphorus-centered radicals: (k) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron 1994, 50, 13533. (l) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1215. (m) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1219. (n) Chuang, C.-P. Tetrahedron Lett. 1992, 33, 6311. (o) Serra, A. C.; da Silva Correa, C. M. M.; do Vale, M. L. C. Tetrahedron 1991, 47, 9463. (p) De Riggi, I.; Surzur, J.-M.; Bertrand, M. P.; Archavlis, A.; Faure, R. Tetrahedron 1990, 46, 5285. (q) Chuang, C.-P. Synlett 1990, 527. (r) Broka, C. A.; Reichert, D. E. C. Tetrahedron Lett. 1987, 28, 1503. (s) Padwa, A. Nimmesgern, H.; Wong, G. S. K. J. Org. Chem. 1985, 50, 5620.
25. 3SnH: (a) Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418. (b) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. (c) Janardhanam, S.; Balakumar, A.; Rajagopalan, K. J. Chem. Soc., Perkin Trans, 1 1994, 551. (d) Janardhanam, S.; Shanmugam, P.; Rajagopalan, K. J. Org. Chem. 1993, 58, 7782. (e) Hanessian, S.; Léger, R. J. Am. Chem. Soc. 1992, 114, 3115. (f) Enholm, E. J.; Kinter, K. S. J. Am. Chem. Soc. 1991, 113, 7784. (g) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc. 1991, 113, 6268. (h) Yang, Z.-Y.; Burton, D. J. J. Org. Chem. 1991, 56, 5125. (i) Stork, G.; Reynolds, M. E. J. Am. Chem. Soc. 1988, 110, 6911. Cyclizations using silicon hydrides: (j) Kopping, B.; Chatgilialoglu, C.; Zehnder, M.; Giese, B. J. Org. Chem. 1992, 57, 3994. Cyclizations using sulfur- and phosphorus-centered radicals: (k) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron 1994, 50, 13533. (l) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1215. (m) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1219. (n) Chuang, C.-P. Tetrahedron Lett. 1992, 33, 6311. (o) Serra, A. C.; da Silva Correa, C. M. M.; do Vale, M. L. C. Tetrahedron 1991, 47, 9463. (p) De Riggi, I.; Surzur, J.-M.; Bertrand, M. P.; Archavlis, A.; Faure, R. Tetrahedron 1990, 46, 5285. (q) Chuang, C.-P. Synlett 1990, 527. (r) Broka, C. A.; Reichert, D. E. C. Tetrahedron Lett. 1987, 28, 1503. (s) Padwa, A. Nimmesgern, H.; Wong, G. S. K. J. Org. Chem. 1985, 50, 5620.
26. 3SnH: (a) Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418. (b) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. (c) Janardhanam, S.; Balakumar, A.; Rajagopalan, K. J. Chem. Soc., Perkin Trans, 1 1994, 551. (d) Janardhanam, S.; Shanmugam, P.; Rajagopalan, K. J. Org. Chem. 1993, 58, 7782. (e) Hanessian, S.; Léger, R. J. Am. Chem. Soc. 1992, 114, 3115. (f) Enholm, E. J.; Kinter, K. S. J. Am. Chem. Soc. 1991, 113, 7784. (g) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc. 1991, 113, 6268. (h) Yang, Z.-Y.; Burton, D. J. J. Org. Chem. 1991, 56, 5125. (i) Stork, G.; Reynolds, M. E. J. Am. Chem. Soc. 1988, 110, 6911. Cyclizations using silicon hydrides: (j) Kopping, B.; Chatgilialoglu, C.; Zehnder, M.; Giese, B. J. Org. Chem. 1992, 57, 3994. Cyclizations using sulfur- and phosphorus-centered radicals: (k) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron 1994, 50, 13533. (l) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1215. (m) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1219. (n) Chuang, C.-P. Tetrahedron Lett. 1992, 33, 6311. (o) Serra, A. C.; da Silva Correa, C. M. M.; do Vale, M. L. C. Tetrahedron 1991, 47, 9463. (p) De Riggi, I.; Surzur, J.-M.; Bertrand, M. P.; Archavlis, A.; Faure, R. Tetrahedron 1990, 46, 5285. (q) Chuang, C.-P. Synlett 1990, 527. (r) Broka, C. A.; Reichert, D. E. C. Tetrahedron Lett. 1987, 28, 1503. (s) Padwa, A. Nimmesgern, H.; Wong, G. S. K. J. Org. Chem. 1985, 50, 5620.
27. 3SnH: (a) Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418. (b) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. (c) Janardhanam, S.; Balakumar, A.; Rajagopalan, K. J. Chem. Soc., Perkin Trans, 1 1994, 551. (d) Janardhanam, S.; Shanmugam, P.; Rajagopalan, K. J. Org. Chem. 1993, 58, 7782. (e) Hanessian, S.; Léger, R. J. Am. Chem. Soc. 1992, 114, 3115. (f) Enholm, E. J.; Kinter, K. S. J. Am. Chem. Soc. 1991, 113, 7784. (g) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc. 1991, 113, 6268. (h) Yang, Z.-Y.; Burton, D. J. J. Org. Chem. 1991, 56, 5125. (i) Stork, G.; Reynolds, M. E. J. Am. Chem. Soc. 1988, 110, 6911. Cyclizations using silicon hydrides: (j) Kopping, B.; Chatgilialoglu, C.; Zehnder, M.; Giese, B. J. Org. Chem. 1992, 57, 3994. Cyclizations using sulfur- and phosphorus-centered radicals: (k) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron 1994, 50, 13533. (l) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1215. (m) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1219. (n) Chuang, C.-P. Tetrahedron Lett. 1992, 33, 6311. (o) Serra, A. C.; da Silva Correa, C. M. M.; do Vale, M. L. C. Tetrahedron 1991, 47, 9463. (p) De Riggi, I.; Surzur, J.-M.; Bertrand, M. P.; Archavlis, A.; Faure, R. Tetrahedron 1990, 46, 5285. (q) Chuang, C.-P. Synlett 1990, 527. (r) Broka, C. A.; Reichert, D. E. C. Tetrahedron Lett. 1987, 28, 1503. (s) Padwa, A. Nimmesgern, H.; Wong, G. S. K. J. Org. Chem. 1985, 50, 5620.
28. 3SnH: (a) Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418. (b) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. (c) Janardhanam, S.; Balakumar, A.; Rajagopalan, K. J. Chem. Soc., Perkin Trans, 1 1994, 551. (d) Janardhanam, S.; Shanmugam, P.; Rajagopalan, K. J. Org. Chem. 1993, 58, 7782. (e) Hanessian, S.; Léger, R. J. Am. Chem. Soc. 1992, 114, 3115. (f) Enholm, E. J.; Kinter, K. S. J. Am. Chem. Soc. 1991, 113, 7784. (g) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc. 1991, 113, 6268. (h) Yang, Z.-Y.; Burton, D. J. J. Org. Chem. 1991, 56, 5125. (i) Stork, G.; Reynolds, M. E. J. Am. Chem. Soc. 1988, 110, 6911. Cyclizations using silicon hydrides: (j) Kopping, B.; Chatgilialoglu, C.; Zehnder, M.; Giese, B. J. Org. Chem. 1992, 57, 3994. Cyclizations using sulfur- and phosphorus-centered radicals: (k) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron 1994, 50, 13533. (l) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1215. (m) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1219. (n) Chuang, C.-P. Tetrahedron Lett. 1992, 33, 6311. (o) Serra, A. C.; da Silva Correa, C. M. M.; do Vale, M. L. C. Tetrahedron 1991, 47, 9463. (p) De Riggi, I.; Surzur, J.-M.; Bertrand, M. P.; Archavlis, A.; Faure, R. Tetrahedron 1990, 46, 5285. (q) Chuang, C.-P. Synlett 1990, 527. (r) Broka, C. A.; Reichert, D. E. C. Tetrahedron Lett. 1987, 28, 1503. (s) Padwa, A. Nimmesgern, H.; Wong, G. S. K. J. Org. Chem. 1985, 50, 5620.
29. 3SnH: (a) Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418. (b) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. (c) Janardhanam, S.; Balakumar, A.; Rajagopalan, K. J. Chem. Soc., Perkin Trans, 1 1994, 551. (d) Janardhanam, S.; Shanmugam, P.; Rajagopalan, K. J. Org. Chem. 1993, 58, 7782. (e) Hanessian, S.; Léger, R. J. Am. Chem. Soc. 1992, 114, 3115. (f) Enholm, E. J.; Kinter, K. S. J. Am. Chem. Soc. 1991, 113, 7784. (g) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc. 1991, 113, 6268. (h) Yang, Z.-Y.; Burton, D. J. J. Org. Chem. 1991, 56, 5125. (i) Stork, G.; Reynolds, M. E. J. Am. Chem. Soc. 1988, 110, 6911. Cyclizations using silicon hydrides: (j) Kopping, B.; Chatgilialoglu, C.; Zehnder, M.; Giese, B. J. Org. Chem. 1992, 57, 3994. Cyclizations using sulfur- and phosphorus-centered radicals: (k) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron 1994, 50, 13533. (l) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1215. (m) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1219. (n) Chuang, C.-P. Tetrahedron Lett. 1992, 33, 6311. (o) Serra, A. C.; da Silva Correa, C. M. M.; do Vale, M. L. C. Tetrahedron 1991, 47, 9463. (p) De Riggi, I.; Surzur, J.-M.; Bertrand, M. P.; Archavlis, A.; Faure, R. Tetrahedron 1990, 46, 5285. (q) Chuang, C.-P. Synlett 1990, 527. (r) Broka, C. A.; Reichert, D. E. C. Tetrahedron Lett. 1987, 28, 1503. (s) Padwa, A. Nimmesgern, H.; Wong, G. S. K. J. Org. Chem. 1985, 50, 5620.
30. 3SnH: (a) Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418. (b) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. (c) Janardhanam, S.; Balakumar, A.; Rajagopalan, K. J. Chem. Soc., Perkin Trans, 1 1994, 551. (d) Janardhanam, S.; Shanmugam, P.; Rajagopalan, K. J. Org. Chem. 1993, 58, 7782. (e) Hanessian, S.; Léger, R. J. Am. Chem. Soc. 1992, 114, 3115. (f) Enholm, E. J.; Kinter, K. S. J. Am. Chem. Soc. 1991, 113, 7784. (g) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc. 1991, 113, 6268. (h) Yang, Z.-Y.; Burton, D. J. J. Org. Chem. 1991, 56, 5125. (i) Stork, G.; Reynolds, M. E. J. Am. Chem. Soc. 1988, 110, 6911. Cyclizations using silicon hydrides: (j) Kopping, B.; Chatgilialoglu, C.; Zehnder, M.; Giese, B. J. Org. Chem. 1992, 57, 3994. Cyclizations using sulfur- and phosphorus-centered radicals: (k) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron 1994, 50, 13533. (l) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1215. (m) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1219. (n) Chuang, C.-P. Tetrahedron Lett. 1992, 33, 6311. (o) Serra, A. C.; da Silva Correa, C. M. M.; do Vale, M. L. C. Tetrahedron 1991, 47, 9463. (p) De Riggi, I.; Surzur, J.-M.; Bertrand, M. P.; Archavlis, A.; Faure, R. Tetrahedron 1990, 46, 5285. (q) Chuang, C.-P. Synlett 1990, 527. (r) Broka, C. A.; Reichert, D. E. C. Tetrahedron Lett. 1987, 28, 1503. (s) Padwa, A. Nimmesgern, H.; Wong, G. S. K. J. Org. Chem. 1985, 50, 5620.
31. 3SnH: (a) Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418. (b) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. (c) Janardhanam, S.; Balakumar, A.; Rajagopalan, K. J. Chem. Soc., Perkin Trans, 1 1994, 551. (d) Janardhanam, S.; Shanmugam, P.; Rajagopalan, K. J. Org. Chem. 1993, 58, 7782. (e) Hanessian, S.; Léger, R. J. Am. Chem. Soc. 1992, 114, 3115. (f) Enholm, E. J.; Kinter, K. S. J. Am. Chem. Soc. 1991, 113, 7784. (g) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc. 1991, 113, 6268. (h) Yang, Z.-Y.; Burton, D. J. J. Org. Chem. 1991, 56, 5125. (i) Stork, G.; Reynolds, M. E. J. Am. Chem. Soc. 1988, 110, 6911. Cyclizations using silicon hydrides: (j) Kopping, B.; Chatgilialoglu, C.; Zehnder, M.; Giese, B. J. Org. Chem. 1992, 57, 3994. Cyclizations using sulfur- and phosphorus-centered radicals: (k) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron 1994, 50, 13533. (l) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1215. (m) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1219. (n) Chuang, C.-P. Tetrahedron Lett. 1992, 33, 6311. (o) Serra, A. C.; da Silva Correa, C. M. M.; do Vale, M. L. C. Tetrahedron 1991, 47, 9463. (p) De Riggi, I.; Surzur, J.-M.; Bertrand, M. P.; Archavlis, A.; Faure, R. Tetrahedron 1990, 46, 5285. (q) Chuang, C.-P. Synlett 1990, 527. (r) Broka, C. A.; Reichert, D. E. C. Tetrahedron Lett. 1987, 28, 1503. (s) Padwa, A. Nimmesgern, H.; Wong, G. S. K. J. Org. Chem. 1985, 50, 5620.
32. 3SnH: (a) Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418. (b) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. (c) Janardhanam, S.; Balakumar, A.; Rajagopalan, K. J. Chem. Soc., Perkin Trans, 1 1994, 551. (d) Janardhanam, S.; Shanmugam, P.; Rajagopalan, K. J. Org. Chem. 1993, 58, 7782. (e) Hanessian, S.; Léger, R. J. Am. Chem. Soc. 1992, 114, 3115. (f) Enholm, E. J.; Kinter, K. S. J. Am. Chem. Soc. 1991, 113, 7784. (g) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc. 1991, 113, 6268. (h) Yang, Z.-Y.; Burton, D. J. J. Org. Chem. 1991, 56, 5125. (i) Stork, G.; Reynolds, M. E. J. Am. Chem. Soc. 1988, 110, 6911. Cyclizations using silicon hydrides: (j) Kopping, B.; Chatgilialoglu, C.; Zehnder, M.; Giese, B. J. Org. Chem. 1992, 57, 3994. Cyclizations using sulfur- and phosphorus-centered radicals: (k) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron 1994, 50, 13533. (l) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1215. (m) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1219. (n) Chuang, C.-P. Tetrahedron Lett. 1992, 33, 6311. (o) Serra, A. C.; da Silva Correa, C. M. M.; do Vale, M. L. C. Tetrahedron 1991, 47, 9463. (p) De Riggi, I.; Surzur, J.-M.; Bertrand, M. P.; Archavlis, A.; Faure, R. Tetrahedron 1990, 46, 5285. (q) Chuang, C.-P. Synlett 1990, 527. (r) Broka, C. A.; Reichert, D. E. C. Tetrahedron Lett. 1987, 28, 1503. (s) Padwa, A. Nimmesgern, H.; Wong, G. S. K. J. Org. Chem. 1985, 50, 5620.
33. 3SnH: (a) Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418. (b) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. (c) Janardhanam, S.; Balakumar, A.; Rajagopalan, K. J. Chem. Soc., Perkin Trans, 1 1994, 551. (d) Janardhanam, S.; Shanmugam, P.; Rajagopalan, K. J. Org. Chem. 1993, 58, 7782. (e) Hanessian, S.; Léger, R. J. Am. Chem. Soc. 1992, 114, 3115. (f) Enholm, E. J.; Kinter, K. S. J. Am. Chem. Soc. 1991, 113, 7784. (g) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc. 1991, 113, 6268. (h) Yang, Z.-Y.; Burton, D. J. J. Org. Chem. 1991, 56, 5125. (i) Stork, G.; Reynolds, M. E. J. Am. Chem. Soc. 1988, 110, 6911. Cyclizations using silicon hydrides: (j) Kopping, B.; Chatgilialoglu, C.; Zehnder, M.; Giese, B. J. Org. Chem. 1992, 57, 3994. Cyclizations using sulfur- and phosphorus-centered radicals: (k) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron 1994, 50, 13533. (l) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1215. (m) Brumwell, J. E.; Simpkins, N. S.; Terret, N. K. Tetrahedron Lett. 1993, 34, 1219. (n) Chuang, C.-P. Tetrahedron Lett. 1992, 33, 6311. (o) Serra, A. C.; da Silva Correa, C. M. M.; do Vale, M. L. C. Tetrahedron 1991, 47, 9463. (p) De Riggi, I.; Surzur, J.-M.; Bertrand, M. P.; Archavlis, A.; Faure, R. Tetrahedron 1990, 46, 5285. (q) Chuang, C.-P. Synlett 1990, 527. (r) Broka, C. A.; Reichert, D. E. C. Tetrahedron Lett. 1987, 28, 1503. (s) Padwa, A. Nimmesgern, H.; Wong, G. S. K. J. Org. Chem. 1985, 50, 5620.
34. For an exhaustive revision of cyclization methodologies to prepare bicyclic β-lactams, see: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1993; Chapter 3. Recent examples related to the synthesis of trinem and trinem derivatives: (b) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (d) Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (e) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (f) Rossi, T.; Marchiro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (d) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (e) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (f) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884. For recent examples on the synthesis of new, different types of polycyclic β-lactams, see: (g) Martel, S. R.; Wisedale, R.; Gallagher, L. D.; Mahon, F.; Badbury, R. H.; Hales, N. J. J. Am. Chem. Soc. 1997, 119, 2309. (h) Planchenault, D.; Wisedale, R.; Gallagher, T.; Hales, N. J. J. Org. Chem. 1997, 62, 3438. (i) Elliot, R. L.; Nicholson, N. H.; Peaker, F. E.; Takle, A. K.; Richardson, C. M.; Tyler, J. W.; White, J.; Pearson, M. J.; Eggleston, D. S.; Haltiwanger, R. C. J. Org. Chem. 1997, 62, 4998. (j) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I. Tetrahedron Lett. 1997, 38, 5913. (k) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T. Tetrahedron 1997, 53, 13129. (l) Banik, B. K; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (m) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 61, 1014. (n) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1996, 60, 6176. (o) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (p) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 19, 2285.
35. For an exhaustive revision of cyclization methodologies to prepare bicyclic β-lactams, see: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1993; Chapter 3. Recent examples related to the synthesis of trinem and trinem derivatives: (b) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (d) Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (e) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (f) Rossi, T.; Marchiro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (d) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (e) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (f) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884. For recent examples on the synthesis of new, different types of polycyclic β-lactams, see: (g) Martel, S. R.; Wisedale, R.; Gallagher, L. D.; Mahon, F.; Badbury, R. H.; Hales, N. J. J. Am. Chem. Soc. 1997, 119, 2309. (h) Planchenault, D.; Wisedale, R.; Gallagher, T.; Hales, N. J. J. Org. Chem. 1997, 62, 3438. (i) Elliot, R. L.; Nicholson, N. H.; Peaker, F. E.; Takle, A. K.; Richardson, C. M.; Tyler, J. W.; White, J.; Pearson, M. J.; Eggleston, D. S.; Haltiwanger, R. C. J. Org. Chem. 1997, 62, 4998. (j) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I. Tetrahedron Lett. 1997, 38, 5913. (k) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T. Tetrahedron 1997, 53, 13129. (l) Banik, B. K; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (m) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 61, 1014. (n) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1996, 60, 6176. (o) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (p) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 19, 2285.
36. For an exhaustive revision of cyclization methodologies to prepare bicyclic β-lactams, see: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1993; Chapter 3. Recent examples related to the synthesis of trinem and trinem derivatives: (b) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (d) Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (e) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (f) Rossi, T.; Marchiro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (d) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (e) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (f) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884. For recent examples on the synthesis of new, different types of polycyclic β-lactams, see: (g) Martel, S. R.; Wisedale, R.; Gallagher, L. D.; Mahon, F.; Badbury, R. H.; Hales, N. J. J. Am. Chem. Soc. 1997, 119, 2309. (h) Planchenault, D.; Wisedale, R.; Gallagher, T.; Hales, N. J. J. Org. Chem. 1997, 62, 3438. (i) Elliot, R. L.; Nicholson, N. H.; Peaker, F. E.; Takle, A. K.; Richardson, C. M.; Tyler, J. W.; White, J.; Pearson, M. J.; Eggleston, D. S.; Haltiwanger, R. C. J. Org. Chem. 1997, 62, 4998. (j) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I. Tetrahedron Lett. 1997, 38, 5913. (k) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T. Tetrahedron 1997, 53, 13129. (l) Banik, B. K; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (m) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 61, 1014. (n) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1996, 60, 6176. (o) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (p) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 19, 2285.
37. For an exhaustive revision of cyclization methodologies to prepare bicyclic β-lactams, see: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1993; Chapter 3. Recent examples related to the synthesis of trinem and trinem derivatives: (b) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (d) Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (e) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (f) Rossi, T.; Marchiro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (d) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (e) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (f) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884. For recent examples on the synthesis of new, different types of polycyclic β-lactams, see: (g) Martel, S. R.; Wisedale, R.; Gallagher, L. D.; Mahon, F.; Badbury, R. H.; Hales, N. J. J. Am. Chem. Soc. 1997, 119, 2309. (h) Planchenault, D.; Wisedale, R.; Gallagher, T.; Hales, N. J. J. Org. Chem. 1997, 62, 3438. (i) Elliot, R. L.; Nicholson, N. H.; Peaker, F. E.; Takle, A. K.; Richardson, C. M.; Tyler, J. W.; White, J.; Pearson, M. J.; Eggleston, D. S.; Haltiwanger, R. C. J. Org. Chem. 1997, 62, 4998. (j) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I. Tetrahedron Lett. 1997, 38, 5913. (k) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T. Tetrahedron 1997, 53, 13129. (l) Banik, B. K; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (m) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 61, 1014. (n) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1996, 60, 6176. (o) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (p) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 19, 2285.
38. For an exhaustive revision of cyclization methodologies to prepare bicyclic β-lactams, see: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1993; Chapter 3. Recent examples related to the synthesis of trinem and trinem derivatives: (b) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (d) Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (e) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (f) Rossi, T.; Marchiro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (d) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (e) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (f) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884. For recent examples on the synthesis of new, different types of polycyclic β-lactams, see: (g) Martel, S. R.; Wisedale, R.; Gallagher, L. D.; Mahon, F.; Badbury, R. H.; Hales, N. J. J. Am. Chem. Soc. 1997, 119, 2309. (h) Planchenault, D.; Wisedale, R.; Gallagher, T.; Hales, N. J. J. Org. Chem. 1997, 62, 3438. (i) Elliot, R. L.; Nicholson, N. H.; Peaker, F. E.; Takle, A. K.; Richardson, C. M.; Tyler, J. W.; White, J.; Pearson, M. J.; Eggleston, D. S.; Haltiwanger, R. C. J. Org. Chem. 1997, 62, 4998. (j) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I. Tetrahedron Lett. 1997, 38, 5913. (k) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T. Tetrahedron 1997, 53, 13129. (l) Banik, B. K; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (m) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 61, 1014. (n) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1996, 60, 6176. (o) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (p) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 19, 2285.
39. For an exhaustive revision of cyclization methodologies to prepare bicyclic β-lactams, see: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1993; Chapter 3. Recent examples related to the synthesis of trinem and trinem derivatives: (b) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (d) Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (e) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (f) Rossi, T.; Marchiro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (d) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (e) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (f) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884. For recent examples on the synthesis of new, different types of polycyclic β-lactams, see: (g) Martel, S. R.; Wisedale, R.; Gallagher, L. D.; Mahon, F.; Badbury, R. H.; Hales, N. J. J. Am. Chem. Soc. 1997, 119, 2309. (h) Planchenault, D.; Wisedale, R.; Gallagher, T.; Hales, N. J. J. Org. Chem. 1997, 62, 3438. (i) Elliot, R. L.; Nicholson, N. H.; Peaker, F. E.; Takle, A. K.; Richardson, C. M.; Tyler, J. W.; White, J.; Pearson, M. J.; Eggleston, D. S.; Haltiwanger, R. C. J. Org. Chem. 1997, 62, 4998. (j) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I. Tetrahedron Lett. 1997, 38, 5913. (k) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T. Tetrahedron 1997, 53, 13129. (l) Banik, B. K; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (m) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 61, 1014. (n) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1996, 60, 6176. (o) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (p) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 19, 2285.
40. For an exhaustive revision of cyclization methodologies to prepare bicyclic β-lactams, see: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1993; Chapter 3. Recent examples related to the synthesis of trinem and trinem derivatives: (b) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (d) Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (e) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (f) Rossi, T.; Marchiro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (d) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (e) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (f) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884. For recent examples on the synthesis of new, different types of polycyclic β-lactams, see: (g) Martel, S. R.; Wisedale, R.; Gallagher, L. D.; Mahon, F.; Badbury, R. H.; Hales, N. J. J. Am. Chem. Soc. 1997, 119, 2309. (h) Planchenault, D.; Wisedale, R.; Gallagher, T.; Hales, N. J. J. Org. Chem. 1997, 62, 3438. (i) Elliot, R. L.; Nicholson, N. H.; Peaker, F. E.; Takle, A. K.; Richardson, C. M.; Tyler, J. W.; White, J.; Pearson, M. J.; Eggleston, D. S.; Haltiwanger, R. C. J. Org. Chem. 1997, 62, 4998. (j) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I. Tetrahedron Lett. 1997, 38, 5913. (k) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T. Tetrahedron 1997, 53, 13129. (l) Banik, B. K; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (m) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 61, 1014. (n) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1996, 60, 6176. (o) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (p) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 19, 2285.
41. For an exhaustive revision of cyclization methodologies to prepare bicyclic β-lactams, see: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1993; Chapter 3. Recent examples related to the synthesis of trinem and trinem derivatives: (b) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (d) Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (e) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (f) Rossi, T.; Marchiro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (d) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (e) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (f) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884. For recent examples on the synthesis of new, different types of polycyclic β-lactams, see: (g) Martel, S. R.; Wisedale, R.; Gallagher, L. D.; Mahon, F.; Badbury, R. H.; Hales, N. J. J. Am. Chem. Soc. 1997, 119, 2309. (h) Planchenault, D.; Wisedale, R.; Gallagher, T.; Hales, N. J. J. Org. Chem. 1997, 62, 3438. (i) Elliot, R. L.; Nicholson, N. H.; Peaker, F. E.; Takle, A. K.; Richardson, C. M.; Tyler, J. W.; White, J.; Pearson, M. J.; Eggleston, D. S.; Haltiwanger, R. C. J. Org. Chem. 1997, 62, 4998. (j) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I. Tetrahedron Lett. 1997, 38, 5913. (k) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T. Tetrahedron 1997, 53, 13129. (l) Banik, B. K; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (m) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 61, 1014. (n) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1996, 60, 6176. (o) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (p) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 19, 2285.
42. For an exhaustive revision of cyclization methodologies to prepare bicyclic β-lactams, see: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1993; Chapter 3. Recent examples related to the synthesis of trinem and trinem derivatives: (b) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (d) Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (e) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (f) Rossi, T.; Marchiro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (d) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (e) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (f) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884. For recent examples on the synthesis of new, different types of polycyclic β-lactams, see: (g) Martel, S. R.; Wisedale, R.; Gallagher, L. D.; Mahon, F.; Badbury, R. H.; Hales, N. J. J. Am. Chem. Soc. 1997, 119, 2309. (h) Planchenault, D.; Wisedale, R.; Gallagher, T.; Hales, N. J. J. Org. Chem. 1997, 62, 3438. (i) Elliot, R. L.; Nicholson, N. H.; Peaker, F. E.; Takle, A. K.; Richardson, C. M.; Tyler, J. W.; White, J.; Pearson, M. J.; Eggleston, D. S.; Haltiwanger, R. C. J. Org. Chem. 1997, 62, 4998. (j) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I. Tetrahedron Lett. 1997, 38, 5913. (k) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T. Tetrahedron 1997, 53, 13129. (l) Banik, B. K; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (m) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 61, 1014. (n) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1996, 60, 6176. (o) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (p) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 19, 2285.
43. For an exhaustive revision of cyclization methodologies to prepare bicyclic β-lactams, see: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1993; Chapter 3. Recent examples related to the synthesis of trinem and trinem derivatives: (b) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (d) Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (e) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (f) Rossi, T.; Marchiro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (d) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (e) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (f) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884. For recent examples on the synthesis of new, different types of polycyclic β-lactams, see: (g) Martel, S. R.; Wisedale, R.; Gallagher, L. D.; Mahon, F.; Badbury, R. H.; Hales, N. J. J. Am. Chem. Soc. 1997, 119, 2309. (h) Planchenault, D.; Wisedale, R.; Gallagher, T.; Hales, N. J. J. Org. Chem. 1997, 62, 3438. (i) Elliot, R. L.; Nicholson, N. H.; Peaker, F. E.; Takle, A. K.; Richardson, C. M.; Tyler, J. W.; White, J.; Pearson, M. J.; Eggleston, D. S.; Haltiwanger, R. C. J. Org. Chem. 1997, 62, 4998. (j) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I. Tetrahedron Lett. 1997, 38, 5913. (k) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T. Tetrahedron 1997, 53, 13129. (l) Banik, B. K; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (m) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org.
44. For an exhaustive revision of cyclization methodologies to prepare bicyclic β-lactams, see: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1993; Chapter 3. Recent examples related to the synthesis of trinem and trinem derivatives: (b) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (d) Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (e) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (f) Rossi, T.; Marchiro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (d) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (e) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (f) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884. For recent examples on the synthesis of new, different types of polycyclic β-lactams, see: (g) Martel, S. R.; Wisedale, R.; Gallagher, L. D.; Mahon, F.; Badbury, R. H.; Hales, N. J. J. Am. Chem. Soc. 1997, 119, 2309. (h) Planchenault, D.; Wisedale, R.; Gallagher, T.; Hales, N. J. J. Org. Chem. 1997, 62, 3438. (i) Elliot, R. L.; Nicholson, N. H.; Peaker, F. E.; Takle, A. K.; Richardson, C. M.; Tyler, J. W.; White, J.; Pearson, M. J.; Eggleston, D. S.; Haltiwanger, R. C. J. Org. Chem. 1997, 62, 4998. (j) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I. Tetrahedron Lett. 1997, 38, 5913. (k) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T. Tetrahedron 1997, 53, 13129. (l) Banik, B. K; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (m) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 61, 1014. (n) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1996, 60, 6176. (o) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (p) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 19, 2285.
45. For an exhaustive revision of cyclization methodologies to prepare bicyclic β-lactams, see: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1993; Chapter 3. Recent examples related to the synthesis of trinem and trinem derivatives: (b) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (d) Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (e) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (f) Rossi, T.; Marchiro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (d) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (e) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (f) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884. For recent examples on the synthesis of new, different types of polycyclic β-lactams, see: (g) Martel, S. R.; Wisedale, R.; Gallagher, L. D.; Mahon, F.; Badbury, R. H.; Hales, N. J. J. Am. Chem. Soc. 1997, 119, 2309. (h) Planchenault, D.; Wisedale, R.; Gallagher, T.; Hales, N. J. J. Org. Chem. 1997, 62, 3438. (i) Elliot, R. L.; Nicholson, N. H.; Peaker, F. E.; Takle, A. K.; Richardson, C. M.; Tyler, J. W.; White, J.; Pearson, M. J.; Eggleston, D. S.; Haltiwanger, R. C. J. Org. Chem. 1997, 62, 4998. (j) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I. Tetrahedron Lett. 1997, 38, 5913. (k) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T. Tetrahedron 1997, 53, 13129. (l) Banik, B. K; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (m) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 61, 1014. (n) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1996, 60, 6176. (o) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (p) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 19, 2285.
46. For an exhaustive revision of cyclization methodologies to prepare bicyclic β-lactams, see: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1993; Chapter 3. Recent examples related to the synthesis of trinem and trinem derivatives: (b) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (d) Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (e) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (f) Rossi, T.; Marchiro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (d) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (e) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (f) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884. For recent examples on the synthesis of new, different types of polycyclic β-lactams, see: (g) Martel, S. R.; Wisedale, R.; Gallagher, L. D.; Mahon, F.; Badbury, R. H.; Hales, N. J. J. Am. Chem. Soc. 1997, 119, 2309. (h) Planchenault, D.; Wisedale, R.; Gallagher, T.; Hales, N. J. J. Org. Chem. 1997, 62, 3438. (i) Elliot, R. L.; Nicholson, N. H.; Peaker, F. E.; Takle, A. K.; Richardson, C. M.; Tyler, J. W.; White, J.; Pearson, M. J.; Eggleston, D. S.; Haltiwanger, R. C. J. Org. Chem. 1997, 62, 4998. (j) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I. Tetrahedron Lett. 1997, 38, 5913. (k) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T. Tetrahedron 1997, 53, 13129. (l) Banik, B. K; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (m) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 61, 1014. (n) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1996, 60, 6176. (o) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (p) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 19, 2285.
47. For an exhaustive revision of cyclization methodologies to prepare bicyclic β-lactams, see: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1993; Chapter 3. Recent examples related to the synthesis of trinem and trinem derivatives: (b) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (d) Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (e) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (f) Rossi, T.; Marchiro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (d) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (e) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (f) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884. For recent examples on the synthesis of new, different types of polycyclic β-lactams, see: (g) Martel, S. R.; Wisedale, R.; Gallagher, L. D.; Mahon, F.; Badbury, R. H.; Hales, N. J. J. Am. Chem. Soc. 1997, 119, 2309. (h) Planchenault, D.; Wisedale, R.; Gallagher, T.; Hales, N. J. J. Org. Chem. 1997, 62, 3438. (i) Elliot, R. L.; Nicholson, N. H.; Peaker, F. E.; Takle, A. K.; Richardson, C. M.; Tyler, J. W.; White, J.; Pearson, M. J.; Eggleston, D. S.; Haltiwanger, R. C. J. Org. Chem. 1997, 62, 4998. (j) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I. Tetrahedron Lett. 1997, 38, 5913. (k) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T. Tetrahedron 1997, 53, 13129. (l) Banik, B. K; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (m) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 61, 1014. (n) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1996, 60, 6176. (o) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (p) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 19, 2285.
48. For an exhaustive revision of cyclization methodologies to prepare bicyclic β-lactams, see: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1993; Chapter 3. Recent examples related to the synthesis of trinem and trinem derivatives: (b) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (d) Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (e) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (f) Rossi, T.; Marchiro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (d) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (e) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (f) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884. For recent examples on the synthesis of new, different types of polycyclic β-lactams, see: (g) Martel, S. R.; Wisedale, R.; Gallagher, L. D.; Mahon, F.; Badbury, R. H.; Hales, N. J. J. Am. Chem. Soc. 1997, 119, 2309. (h) Planchenault, D.; Wisedale, R.; Gallagher, T.; Hales, N. J. J. Org. Chem. 1997, 62, 3438. (i) Elliot, R. L.; Nicholson, N. H.; Peaker, F. E.; Takle, A. K.; Richardson, C. M.; Tyler, J. W.; White, J.; Pearson, M. J.; Eggleston, D. S.; Haltiwanger, R. C. J. Org. Chem. 1997, 62, 4998. (j) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I. Tetrahedron Lett. 1997, 38, 5913. (k) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T. Tetrahedron 1997, 53, 13129. (l) Banik, B. K; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (m) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 61, 1014. (n) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1996, 60, 6176. (o) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (p) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 19, 2285.
49. For an exhaustive revision of cyclization methodologies to prepare bicyclic β-lactams, see: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1993; Chapter 3. Recent examples related to the synthesis of trinem and trinem derivatives: (b) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (d) Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (e) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (f) Rossi, T.; Marchiro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (d) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (e) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (f) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884. For recent examples on the synthesis of new, different types of polycyclic β-lactams, see: (g) Martel, S. R.; Wisedale, R.; Gallagher, L. D.; Mahon, F.; Badbury, R. H.; Hales, N. J. J. Am. Chem. Soc. 1997, 119, 2309. (h) Planchenault, D.; Wisedale, R.; Gallagher, T.; Hales, N. J. J. Org. Chem. 1997, 62, 3438. (i) Elliot, R. L.; Nicholson, N. H.; Peaker, F. E.; Takle, A. K.; Richardson, C. M.; Tyler, J. W.; White, J.; Pearson, M. J.; Eggleston, D. S.; Haltiwanger, R. C. J. Org. Chem. 1997, 62, 4998. (j) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I. Tetrahedron Lett. 1997, 38, 5913. (k) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T. Tetrahedron 1997, 53, 13129. (l) Banik, B. K; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (m) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 61, 1014. (n) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1996, 60, 6176. (o) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (p) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 19, 2285.
50. For an exhaustive revision of cyclization methodologies to prepare bicyclic β-lactams, see: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1993; Chapter 3. Recent examples related to the synthesis of trinem and trinem derivatives: (b) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (d) Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (e) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (f) Rossi, T.; Marchiro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (d) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (e) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (f) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884. For recent examples on the synthesis of new, different types of polycyclic β-lactams, see: (g) Martel, S. R.; Wisedale, R.; Gallagher, L. D.; Mahon, F.; Badbury, R. H.; Hales, N. J. J. Am. Chem. Soc. 1997, 119, 2309. (h) Planchenault, D.; Wisedale, R.; Gallagher, T.; Hales, N. J. J. Org. Chem. 1997, 62, 3438. (i) Elliot, R. L.; Nicholson, N. H.; Peaker, F. E.; Takle, A. K.; Richardson, C. M.; Tyler, J. W.; White, J.; Pearson, M. J.; Eggleston, D. S.; Haltiwanger, R. C. J. Org. Chem. 1997, 62, 4998. (j) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I. Tetrahedron Lett. 1997, 38, 5913. (k) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T. Tetrahedron 1997, 53, 13129. (l) Banik, B. K; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (m) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 61, 1014. (n) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1996, 60, 6176. (o) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (p) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 19, 2285.
51. For an exhaustive revision of cyclization methodologies to prepare bicyclic β-lactams, see: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1993; Chapter 3. Recent examples related to the synthesis of trinem and trinem derivatives: (b) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (d) Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (e) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (f) Rossi, T.; Marchiro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (d) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (e) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (f) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884. For recent examples on the synthesis of new, different types of polycyclic β-lactams, see: (g) Martel, S. R.; Wisedale, R.; Gallagher, L. D.; Mahon, F.; Badbury, R. H.; Hales, N. J. J. Am. Chem. Soc. 1997, 119, 2309. (h) Planchenault, D.; Wisedale, R.; Gallagher, T.; Hales, N. J. J. Org. Chem. 1997, 62, 3438. (i) Elliot, R. L.; Nicholson, N. H.; Peaker, F. E.; Takle, A. K.; Richardson, C. M.; Tyler, J. W.; White, J.; Pearson, M. J.; Eggleston, D. S.; Haltiwanger, R. C. J. Org. Chem. 1997, 62, 4998. (j) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I. Tetrahedron Lett. 1997, 38, 5913. (k) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T. Tetrahedron 1997, 53, 13129. (l) Banik, B. K; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (m) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 61, 1014. (n) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1996, 60, 6176. (o) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (p) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 19, 2285.
52. For excellent articles on the bacterian resistance to the commonly used antibiotics, see: (a) Hook, V. Chem. Br. 1997, 33, 34. (b) Niccolai, D.; Tarsi, L.; Thomas, R. J. Chem, Commun. 1997, 2333. (c) Spratt, B. G. Science 1994, 264, 388-393.
53. For excellent articles on the bacterian resistance to the commonly used antibiotics, see: (a) Hook, V. Chem. Br. 1997, 33, 34. (b) Niccolai, D.; Tarsi, L.; Thomas, R. J. Chem, Commun. 1997, 2333. (c) Spratt, B. G. Science 1994, 264, 388-393.
54. For excellent articles on the bacterian resistance to the commonly used antibiotics, see: (a) Hook, V. Chem. Br. 1997, 33, 34. (b) Niccolai, D.; Tarsi, L.; Thomas, R. J. Chem, Commun. 1997, 2333. (c) Spratt, B. G. Science 1994, 264, 388-393.
55. (a) Knight, J.; Parsons, P. J.; Southgate, R. J. Chem. Soc., Chem. Commun. 1986, 78.
56. (b) Knight, J.; Parsons, P. J. J. Chem. Soc., Perkin Trans. 1 1987, 1237.
57. See, for example: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: Weinheim, 1993; Chapter 3, pp 159-167. (b) Bachi, M. D. In Recent Advances in the Chemistry of β-Lactam Antibiotics; Bentley, P. H., Southgate, R., Eds.; Spec. Pub. No. 70; R. Soc. Chem.: London, 1989; Chapter 6. (c) Bachi, M. D.; Hoornaert, C. Tetrahedron Lett. 1981, 22, 2689. (d) Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (e) Beckwith, A. L. J.; Boate, D. R. Tetrahedron Lett. 1985, 26, 1761. (f) Kametani, T.; Chu, Sh.-D.; Itoh, A.; Maeda, S.; Honda, T. J. Org. Chem. 1988, 53, 2683. (d) Anaya, J.; Barton, D. H. R.; Gero, S. D.; Grande, M.; Martin, N.; Tachdijian, C. Angew. Chem., Int. Ed. Engl. 1993, 32, 867. (e) Bachi, M. D.; Bar-Ner, N. BioMed. Chem. Lett. 1993, 3, 2439 and references therein.
58. See, for example: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: Weinheim, 1993; Chapter 3, pp 159-167. (b) Bachi, M. D. In Recent Advances in the Chemistry of β-Lactam Antibiotics; Bentley, P. H., Southgate, R., Eds.; Spec. Pub. No. 70; R. Soc. Chem.: London, 1989; Chapter 6. (c) Bachi, M. D.; Hoornaert, C. Tetrahedron Lett. 1981, 22, 2689. (d) Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (e) Beckwith, A. L. J.; Boate, D. R. Tetrahedron Lett. 1985, 26, 1761. (f) Kametani, T.; Chu, Sh.-D.; Itoh, A.; Maeda, S.; Honda, T. J. Org. Chem. 1988, 53, 2683. (d) Anaya, J.; Barton, D. H. R.; Gero, S. D.; Grande, M.; Martin, N.; Tachdijian, C. Angew. Chem., Int. Ed. Engl. 1993, 32, 867. (e) Bachi, M. D.; Bar-Ner, N. BioMed. Chem. Lett. 1993, 3, 2439 and references therein.
59. See, for example: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: Weinheim, 1993; Chapter 3, pp 159-167. (b) Bachi, M. D. In Recent Advances in the Chemistry of β-Lactam Antibiotics; Bentley, P. H., Southgate, R., Eds.; Spec. Pub. No. 70; R. Soc. Chem.: London, 1989; Chapter 6. (c) Bachi, M. D.; Hoornaert, C. Tetrahedron Lett. 1981, 22, 2689. (d) Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (e) Beckwith, A. L. J.; Boate, D. R. Tetrahedron Lett. 1985, 26, 1761. (f) Kametani, T.; Chu, Sh.-D.; Itoh, A.; Maeda, S.; Honda, T. J. Org. Chem. 1988, 53, 2683. (d) Anaya, J.; Barton, D. H. R.; Gero, S. D.; Grande, M.; Martin, N.; Tachdijian, C. Angew. Chem., Int. Ed. Engl. 1993, 32, 867. (e) Bachi, M. D.; Bar-Ner, N. BioMed. Chem. Lett. 1993, 3, 2439 and references therein.
60. See, for example: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: Weinheim, 1993; Chapter 3, pp 159-167. (b) Bachi, M. D. In Recent Advances in the Chemistry of β-Lactam Antibiotics; Bentley, P. H., Southgate, R., Eds.; Spec. Pub. No. 70; R. Soc. Chem.: London, 1989; Chapter 6. (c) Bachi, M. D.; Hoornaert, C. Tetrahedron Lett. 1981, 22, 2689. (d) Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (e) Beckwith, A. L. J.; Boate, D. R. Tetrahedron Lett. 1985, 26, 1761. (f) Kametani, T.; Chu, Sh.-D.; Itoh, A.; Maeda, S.; Honda, T. J. Org. Chem. 1988, 53, 2683. (d) Anaya, J.; Barton, D. H. R.; Gero, S. D.; Grande, M.; Martin, N.; Tachdijian, C. Angew. Chem., Int. Ed. Engl. 1993, 32, 867. (e) Bachi, M. D.; Bar-Ner, N. BioMed. Chem. Lett. 1993, 3, 2439 and references therein.
61. See, for example: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: Weinheim, 1993; Chapter 3, pp 159-167. (b) Bachi, M. D. In Recent Advances in the Chemistry of β-Lactam Antibiotics; Bentley, P. H., Southgate, R., Eds.; Spec. Pub. No. 70; R. Soc. Chem.: London, 1989; Chapter 6. (c) Bachi, M. D.; Hoornaert, C. Tetrahedron Lett. 1981, 22, 2689. (d) Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (e) Beckwith, A. L. J.; Boate, D. R. Tetrahedron Lett. 1985, 26, 1761. (f) Kametani, T.; Chu, Sh.-D.; Itoh, A.; Maeda, S.; Honda, T. J. Org. Chem. 1988, 53, 2683. (d) Anaya, J.; Barton, D. H. R.; Gero, S. D.; Grande, M.; Martin, N.; Tachdijian, C. Angew. Chem., Int. Ed. Engl. 1993, 32, 867. (e) Bachi, M. D.; Bar-Ner, N. BioMed. Chem. Lett. 1993, 3, 2439 and references therein.
62. See, for example: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: Weinheim, 1993; Chapter 3, pp 159-167. (b) Bachi, M. D. In Recent Advances in the Chemistry of β-Lactam Antibiotics; Bentley, P. H., Southgate, R., Eds.; Spec. Pub. No. 70; R. Soc. Chem.: London, 1989; Chapter 6. (c) Bachi, M. D.; Hoornaert, C. Tetrahedron Lett. 1981, 22, 2689. (d) Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (e) Beckwith, A. L. J.; Boate, D. R. Tetrahedron Lett. 1985, 26, 1761. (f) Kametani, T.; Chu, Sh.-D.; Itoh, A.; Maeda, S.; Honda, T. J. Org. Chem. 1988, 53, 2683. (d) Anaya, J.; Barton, D. H. R.; Gero, S. D.; Grande, M.; Martin, N.; Tachdijian, C. Angew. Chem., Int. Ed. Engl. 1993, 32, 867. (e) Bachi, M. D.; Bar-Ner, N. BioMed. Chem. Lett. 1993, 3, 2439 and references therein.
63. See, for example: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: Weinheim, 1993; Chapter 3, pp 159-167. (b) Bachi, M. D. In Recent Advances in the Chemistry of β-Lactam Antibiotics; Bentley, P. H., Southgate, R., Eds.; Spec. Pub. No. 70; R. Soc. Chem.: London, 1989; Chapter 6. (c) Bachi, M. D.; Hoornaert, C. Tetrahedron Lett. 1981, 22, 2689. (d) Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (e) Beckwith, A. L. J.; Boate, D. R. Tetrahedron Lett. 1985, 26, 1761. (f) Kametani, T.; Chu, Sh.-D.; Itoh, A.; Maeda, S.; Honda, T. J. Org. Chem. 1988, 53, 2683. (d) Anaya, J.; Barton, D. H. R.; Gero, S. D.; Grande, M.; Martin, N.; Tachdijian, C. Angew. Chem., Int. Ed. Engl. 1993, 32, 867. (e) Bachi, M. D.; Bar-Ner, N. BioMed. Chem. Lett. 1993, 3, 2439 and references therein.
64. See, for example: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: Weinheim, 1993; Chapter 3, pp 159-167. (b) Bachi, M. D. In Recent Advances in the Chemistry of β-Lactam Antibiotics; Bentley, P. H., Southgate, R., Eds.; Spec. Pub. No. 70; R. Soc. Chem.: London, 1989; Chapter 6. (c) Bachi, M. D.; Hoornaert, C. Tetrahedron Lett. 1981, 22, 2689. (d) Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (e) Beckwith, A. L. J.; Boate, D. R. Tetrahedron Lett. 1985, 26, 1761. (f) Kametani, T.; Chu, Sh.-D.; Itoh, A.; Maeda, S.; Honda, T. J. Org. Chem. 1988, 53, 2683. (d) Anaya, J.; Barton, D. H. R.; Gero, S. D.; Grande, M.; Martin, N.; Tachdijian, C. Angew. Chem., Int. Ed. Engl. 1993, 32, 867. (e) Bachi, M. D.; Bar-Ner, N. BioMed. Chem. Lett. 1993, 3, 2439 and references therein.
65. Bosch, E.; Bachi, M. D. J. Org. Chem. 1993, 58, 5581.
66. See, for example: (a) Alcaide, B.; Rodríguez-Vicente, A. Tetrahedron Lett. 1998, 39, 6589. (b) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125. (c) Alcaide, B.; Rodríguez-Vicente, A.; Sierra, M. A. Tetrahedron: Asymmetry 1996, 7, 2203. (d) Alcaide, B.; Pérez-Castells, J.; Sánchez-Vigo, B.; Sierra, M. A. BioMed. Chem. Lett. 1993, 3, 2369.
67. See, for example: (a) Alcaide, B.; Rodríguez-Vicente, A. Tetrahedron Lett. 1998, 39, 6589. (b) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125. (c) Alcaide, B.; Rodríguez-Vicente, A.; Sierra, M. A. Tetrahedron: Asymmetry 1996, 7, 2203. (d) Alcaide, B.; Pérez-Castells, J.; Sánchez-Vigo, B.; Sierra, M. A. BioMed. Chem. Lett. 1993, 3, 2369.
68. See, for example: (a) Alcaide, B.; Rodríguez-Vicente, A. Tetrahedron Lett. 1998, 39, 6589. (b) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125. (c) Alcaide, B.; Rodríguez-Vicente, A.; Sierra, M. A. Tetrahedron: Asymmetry 1996, 7, 2203. (d) Alcaide, B.; Pérez-Castells, J.; Sánchez-Vigo, B.; Sierra, M. A. BioMed. Chem. Lett. 1993, 3, 2369.
69. See, for example: (a) Alcaide, B.; Rodríguez-Vicente, A. Tetrahedron Lett. 1998, 39, 6589. (b) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125. (c) Alcaide, B.; Rodríguez-Vicente, A.; Sierra, M. A. Tetrahedron: Asymmetry 1996, 7, 2203. (d) Alcaide, B.; Pérez-Castells, J.; Sánchez-Vigo, B.; Sierra, M. A. BioMed. Chem. Lett. 1993, 3, 2369.
70. (a) Alcaide, B.; Polanco, C.; Sierra, M. A. J. Org. Chem. 1998, 63, 6786.
71. (b) Alcaide, B.; Polanco, C.; Sierra, M. A. Tetrahedron Lett. 1996, 37, 6901.
72. The interest in carbapenams and carbacepham rests in their structural similarity to the carbapenem- and carbacephem-type compounds, which are highly active, broad-spectrum antibiotics with β-lactamase resistance. For reviews on the synthesis of carbapenem, see: (a) Ratcliffe, R. W.; Albers-Schonberg, G. In Chemistry and Biology of β-Lactam Antibiotics; Morin, R. B., Gorman, M., Eds.; Academic Press: New York, 1982, Vol. 2, p 227. (b) Kametani, T.; Fukumoto, K.; Ihara, M. Heterocycles 1982, 17, 463. (c) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (d) Georg, G. I. In Studies in Natural Products Synthesis; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1989; Vol. 4, p 431. (e) Palomo, C. In Recent Progress in the Chemical Synthesis of Antibiotics; Springer-Verlag: Berlin-Heidelberg, 1990; p 565. (f) Berks, A. H. Tetrahedron 1996, 52, 331. For recent reviews on the synthesis of carbacephems: (g) Cooper, R. D. G. In The Chemistry of β-Lactams; Page, M. I., Ed.; Chapman and Hall: London, 1992; Chapter 8. (h) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: Weinheim, 1993; Chapter 3, p 121.
73. The interest in carbapenams and carbacepham rests in their structural similarity to the carbapenem- and carbacephem-type compounds, which are highly active, broad-spectrum antibiotics with β-lactamase resistance. For reviews on the synthesis of carbapenem, see: (a) Ratcliffe, R. W.; Albers-Schonberg, G. In Chemistry and Biology of β-Lactam Antibiotics; Morin, R. B., Gorman, M., Eds.; Academic Press: New York, 1982, Vol. 2, p 227. (b) Kametani, T.; Fukumoto, K.; Ihara, M. Heterocycles 1982, 17, 463. (c) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (d) Georg, G. I. In Studies in Natural Products Synthesis; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1989; Vol. 4, p 431. (e) Palomo, C. In Recent Progress in the Chemical Synthesis of Antibiotics; Springer-Verlag: Berlin-Heidelberg, 1990; p 565. (f) Berks, A. H. Tetrahedron 1996, 52, 331. For recent reviews on the synthesis of carbacephems: (g) Cooper, R. D. G. In The Chemistry of β-Lactams; Page, M. I., Ed.; Chapman and Hall: London, 1992; Chapter 8. (h) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: Weinheim, 1993; Chapter 3, p 121.
74. The interest in carbapenams and carbacepham rests in their structural similarity to the carbapenem- and carbacephem-type compounds, which are highly active, broad-spectrum antibiotics with β-lactamase resistance. For reviews on the synthesis of carbapenem, see: (a) Ratcliffe, R. W.; Albers-Schonberg, G. In Chemistry and Biology of β-Lactam Antibiotics; Morin, R. B., Gorman, M., Eds.; Academic Press: New York, 1982, Vol. 2, p 227. (b) Kametani, T.; Fukumoto, K.; Ihara, M. Heterocycles 1982, 17, 463. (c) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (d) Georg, G. I. In Studies in Natural Products Synthesis; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1989; Vol. 4, p 431. (e) Palomo, C. In Recent Progress in the Chemical Synthesis of Antibiotics; Springer-Verlag: Berlin-Heidelberg, 1990; p 565. (f) Berks, A. H. Tetrahedron 1996, 52, 331. For recent reviews on the synthesis of carbacephems: (g) Cooper, R. D. G. In The Chemistry of β-Lactams; Page, M. I., Ed.; Chapman and Hall: London, 1992; Chapter 8. (h) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: Weinheim, 1993; Chapter 3, p 121.
75. The interest in carbapenams and carbacepham rests in their structural similarity to the carbapenem- and carbacephem-type compounds, which are highly active, broad-spectrum antibiotics with β-lactamase resistance. For reviews on the synthesis of carbapenem, see: (a) Ratcliffe, R. W.; Albers-Schonberg, G. In Chemistry and Biology of β-Lactam Antibiotics; Morin, R. B., Gorman, M., Eds.; Academic Press: New York, 1982, Vol. 2, p 227. (b) Kametani, T.; Fukumoto, K.; Ihara, M. Heterocycles 1982, 17, 463. (c) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (d) Georg, G. I. In Studies in Natural Products Synthesis; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1989; Vol. 4, p 431. (e) Palomo, C. In Recent Progress in the Chemical Synthesis of Antibiotics; Springer-Verlag: Berlin-Heidelberg, 1990; p 565. (f) Berks, A. H. Tetrahedron 1996, 52, 331. For recent reviews on the synthesis of carbacephems: (g) Cooper, R. D. G. In The Chemistry of β-Lactams; Page, M. I., Ed.; Chapman and Hall: London, 1992; Chapter 8. (h) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: Weinheim, 1993; Chapter 3, p 121.
76. The interest in carbapenams and carbacepham rests in their structural similarity to the carbapenem- and carbacephem-type compounds, which are highly active, broad-spectrum antibiotics with β-lactamase resistance. For reviews on the synthesis of carbapenem, see: (a) Ratcliffe, R. W.; Albers-Schonberg, G. In Chemistry and Biology of β-Lactam Antibiotics; Morin, R. B., Gorman, M., Eds.; Academic Press: New York, 1982, Vol. 2, p 227. (b) Kametani, T.; Fukumoto, K.; Ihara, M. Heterocycles 1982, 17, 463. (c) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (d) Georg, G. I. In Studies in Natural Products Synthesis; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1989; Vol. 4, p 431. (e) Palomo, C. In Recent Progress in the Chemical Synthesis of Antibiotics; Springer-Verlag: Berlin-Heidelberg, 1990; p 565. (f) Berks, A. H. Tetrahedron 1996, 52, 331. For recent reviews on the synthesis of carbacephems: (g) Cooper, R. D. G. In The Chemistry of β-Lactams; Page, M. I., Ed.; Chapman and Hall: London, 1992; Chapter 8. (h) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: Weinheim, 1993; Chapter 3, p 121.
77. The interest in carbapenams and carbacepham rests in their structural similarity to the carbapenem- and carbacephem-type compounds, which are highly active, broad-spectrum antibiotics with β-lactamase resistance. For reviews on the synthesis of carbapenem, see: (a) Ratcliffe, R. W.; Albers-Schonberg, G. In Chemistry and Biology of β-Lactam Antibiotics; Morin, R. B., Gorman, M., Eds.; Academic Press: New York, 1982, Vol. 2, p 227. (b) Kametani, T.; Fukumoto, K.; Ihara, M. Heterocycles 1982, 17, 463. (c) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (d) Georg, G. I. In Studies in Natural Products Synthesis; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1989; Vol. 4, p 431. (e) Palomo, C. In Recent Progress in the Chemical Synthesis of Antibiotics; Springer-Verlag: Berlin-Heidelberg, 1990; p 565. (f) Berks, A. H. Tetrahedron 1996, 52, 331. For recent reviews on the synthesis of carbacephems: (g) Cooper, R. D. G. In The Chemistry of β-Lactams; Page, M. I., Ed.; Chapman and Hall: London, 1992; Chapter 8. (h) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: Weinheim, 1993; Chapter 3, p 121.
78. The interest in carbapenams and carbacepham rests in their structural similarity to the carbapenem- and carbacephem-type compounds, which are highly active, broad-spectrum antibiotics with β-lactamase resistance. For reviews on the synthesis of carbapenem, see: (a) Ratcliffe, R. W.; Albers-Schonberg, G. In Chemistry and Biology of β-Lactam Antibiotics; Morin, R. B., Gorman, M., Eds.; Academic Press: New York, 1982, Vol. 2, p 227. (b) Kametani, T.; Fukumoto, K.; Ihara, M. Heterocycles 1982, 17, 463. (c) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (d) Georg, G. I. In Studies in Natural Products Synthesis; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1989; Vol. 4, p 431. (e) Palomo, C. In Recent Progress in the Chemical Synthesis of Antibiotics; Springer-Verlag: Berlin-Heidelberg, 1990; p 565. (f) Berks, A. H. Tetrahedron 1996, 52, 331. For recent reviews on the synthesis of carbacephems: (g) Cooper, R. D. G. In The Chemistry of β-Lactams; Page, M. I., Ed.; Chapman and Hall: London, 1992; Chapter 8. (h) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: Weinheim, 1993; Chapter 3, p 121.
79. The interest in carbapenams and carbacepham rests in their structural similarity to the carbapenem- and carbacephem-type compounds, which are highly active, broad-spectrum antibiotics with β-lactamase resistance. For reviews on the synthesis of carbapenem, see: (a) Ratcliffe, R. W.; Albers-Schonberg, G. In Chemistry and Biology of β-Lactam Antibiotics; Morin, R. B., Gorman, M., Eds.; Academic Press: New York, 1982, Vol. 2, p 227. (b) Kametani, T.; Fukumoto, K.; Ihara, M. Heterocycles 1982, 17, 463. (c) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (d) Georg, G. I. In Studies in Natural Products Synthesis; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1989; Vol. 4, p 431. (e) Palomo, C. In Recent Progress in the Chemical Synthesis of Antibiotics; Springer-Verlag: Berlin-Heidelberg, 1990; p 565. (f) Berks, A. H. Tetrahedron 1996, 52, 331. For recent reviews on the synthesis of carbacephems: (g) Cooper, R. D. G. In The Chemistry of β-Lactams; Page, M. I., Ed.; Chapman and Hall: London, 1992; Chapter 8. (h) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: Weinheim, 1993; Chapter 3, p 121.
80. Bicyclic β-lactams having the lactam group adjacent to the ring fusion point have been reported. See, for example: (a) Ren, X.-F.; Turos, E. J. Org. Chem. 1994, 59, 5858. (b) Ren, X.-F.; Konaklieva, M. I.; Turos, E. J. Org. Chem. 1995, 60, 4980 and references therein.
81. Bicyclic β-lactams having the lactam group adjacent to the ring fusion point have been reported. See, for example: (a) Ren, X.-F.; Turos, E. J. Org. Chem. 1994, 59, 5858. (b) Ren, X.-F.; Konaklieva, M. I.; Turos, E. J. Org. Chem. 1995, 60, 4980 and references therein.
82. For a recent asymmetric synthesis of cispentacin, see: (a) Davies, S. G.; Ichihara, O.; Walters, I. A. S. Synlett 1993, 461. (b) Davies, S. G.; Ichihara, O.; Lenoir, I.; Walters, I. A. S. J. Chem. Soc., Perkin Trans. 1 1994, 1411 and references therein.
83. For a recent asymmetric synthesis of cispentacin, see: (a) Davies, S. G.; Ichihara, O.; Walters, I. A. S. Synlett 1993, 461. (b) Davies, S. G.; Ichihara, O.; Lenoir, I.; Walters, I. A. S. J. Chem. Soc., Perkin Trans. 1 1994, 1411 and references therein.
84. (a) Staudinger, M. Liebigs Ann. Chem. 1907, 356, 51. For recent reviews on the asymmetric ketene-imine approach to β-lactams, see:
85. (b) Georg, G. I.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: Weinheim, 1993; Chapter 3, p 295.
86. (c) van der Steen, F. H.; van Koten, G. Tetrahedron 1991, 47, 7503.
87. (d) Cooper, R. D. G.; Daugherty, B. W.; Boyd, D. B. Pure Appl. Chem. 1987, 59, 485. For comprehensive general reviews of the synthesis of β-lactams, see:
88. (e) Koppel, G. A. In Small Ring Heterocycles; Hassner, A., Ed.; Wiley: New York, 1983; Vol. 42, p 219.
89. (f) Ghosez, L.; Marchand-Brynaert, J. In Comprehensive Organic Synthesis; Trost, B., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 85.
90. (g) DeKimpe, N. In Comprehensive Heterocyclic Chemistry II; Padwa, A., Ed.; Elsevier: Oxford, 1996; Vol. 1B, p 507.
91. Arrieta, A.; Lecea, B.; Cossío, F. P.; Palomo, C. J. Org. Chem. 1988, 53, 3784-3791.
92. The cis/trans-selectivity observed for compounds 1-6 was expected according to the current model for the Staüdinger reaction. (a) Arrieta, A.; Lecea, B.; Cossío, F. P. J. Org. Chem. 1998, 63, 5869. (b) Palomo, C.; Aizpurua, J. M.; Mielgo, A.; Linden, A. J. Org. Chem. 1998, 61, 9186. (c) Cossio, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085. (d) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784. This model accounts for the 3R,4S stereochemistry of 2-azetidinones derived from D-glyceraldehyde. For an experimental study on the synthesis of 2-azetidinones derived from D- and L-glyceraldehyde acetonide imines, see: (e) Niu, Ch.; Miller, M. J. Tetrahedron Lett. 1995, 36, 497. (f) Hubschwerlen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (g) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (h) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227 and references therein.
93. The cis/trans-selectivity observed for compounds 1-6 was expected according to the current model for the Staüdinger reaction. (a) Arrieta, A.; Lecea, B.; Cossío, F. P. J. Org. Chem. 1998, 63, 5869. (b) Palomo, C.; Aizpurua, J. M.; Mielgo, A.; Linden, A. J. Org. Chem. 1998, 61, 9186. (c) Cossio, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085. (d) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784. This model accounts for the 3R,4S stereochemistry of 2-azetidinones derived from D-glyceraldehyde. For an experimental study on the synthesis of 2-azetidinones derived from D- and L-glyceraldehyde acetonide imines, see: (e) Niu, Ch.; Miller, M. J. Tetrahedron Lett. 1995, 36, 497. (f) Hubschwerlen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (g) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (h) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227 and references therein.
94. The cis/trans-selectivity observed for compounds 1-6 was expected according to the current model for the Staüdinger reaction. (a) Arrieta, A.; Lecea, B.; Cossío, F. P. J. Org. Chem. 1998, 63, 5869. (b) Palomo, C.; Aizpurua, J. M.; Mielgo, A.; Linden, A. J. Org. Chem. 1998, 61, 9186. (c) Cossio, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085. (d) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784. This model accounts for the 3R,4S stereochemistry of 2-azetidinones derived from D-glyceraldehyde. For an experimental study on the synthesis of 2-azetidinones derived from D- and L-glyceraldehyde acetonide imines, see: (e) Niu, Ch.; Miller, M. J. Tetrahedron Lett. 1995, 36, 497. (f) Hubschwerlen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (g) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (h) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227 and references therein.
95. The cis/trans-selectivity observed for compounds 1-6 was expected according to the current model for the Staüdinger reaction. (a) Arrieta, A.; Lecea, B.; Cossío, F. P. J. Org. Chem. 1998, 63, 5869. (b) Palomo, C.; Aizpurua, J. M.; Mielgo, A.; Linden, A. J. Org. Chem. 1998, 61, 9186. (c) Cossio, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085. (d) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784. This model accounts for the 3R,4S stereochemistry of 2-azetidinones derived from D-glyceraldehyde. For an experimental study on the synthesis of 2-azetidinones derived from D- and L-glyceraldehyde acetonide imines, see: (e) Niu, Ch.; Miller, M. J. Tetrahedron Lett. 1995, 36, 497. (f) Hubschwerlen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (g) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (h) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227 and references therein.
96. The cis/trans-selectivity observed for compounds 1-6 was expected according to the current model for the Staüdinger reaction. (a) Arrieta, A.; Lecea, B.; Cossío, F. P. J. Org. Chem. 1998, 63, 5869. (b) Palomo, C.; Aizpurua, J. M.; Mielgo, A.; Linden, A. J. Org. Chem. 1998, 61, 9186. (c) Cossio, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085. (d) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784. This model accounts for the 3R,4S stereochemistry of 2-azetidinones derived from D-glyceraldehyde. For an experimental study on the synthesis of 2-azetidinones derived from D- and L-glyceraldehyde acetonide imines, see: (e) Niu, Ch.; Miller, M. J. Tetrahedron Lett. 1995, 36, 497. (f) Hubschwerlen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (g) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (h) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227 and references therein.
97. The cis/trans-selectivity observed for compounds 1-6 was expected according to the current model for the Staüdinger reaction. (a) Arrieta, A.; Lecea, B.; Cossío, F. P. J. Org. Chem. 1998, 63, 5869. (b) Palomo, C.; Aizpurua, J. M.; Mielgo, A.; Linden, A. J. Org. Chem. 1998, 61, 9186. (c) Cossio, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085. (d) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784. This model accounts for the 3R,4S stereochemistry of 2-azetidinones derived from D-glyceraldehyde. For an experimental study on the synthesis of 2-azetidinones derived from D- and L-glyceraldehyde acetonide imines, see: (e) Niu, Ch.; Miller, M. J. Tetrahedron Lett. 1995, 36, 497. (f) Hubschwerlen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (g) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (h) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227 and references therein.
98. The cis/trans-selectivity observed for compounds 1-6 was expected according to the current model for the Staüdinger reaction. (a) Arrieta, A.; Lecea, B.; Cossío, F. P. J. Org. Chem. 1998, 63, 5869. (b) Palomo, C.; Aizpurua, J. M.; Mielgo, A.; Linden, A. J. Org. Chem. 1998, 61, 9186. (c) Cossio, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085. (d) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784. This model accounts for the 3R,4S stereochemistry of 2-azetidinones derived from D-glyceraldehyde. For an experimental study on the synthesis of 2-azetidinones derived from D- and L-glyceraldehyde acetonide imines, see: (e) Niu, Ch.; Miller, M. J. Tetrahedron Lett. 1995, 36, 497. (f) Hubschwerlen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (g) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (h) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227 and references therein.
99. The cis/trans-selectivity observed for compounds 1-6 was expected according to the current model for the Staüdinger reaction. (a) Arrieta, A.; Lecea, B.; Cossío, F. P. J. Org. Chem. 1998, 63, 5869. (b) Palomo, C.; Aizpurua, J. M.; Mielgo, A.; Linden, A. J. Org. Chem. 1998, 61, 9186. (c) Cossio, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085. (d) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784. This model accounts for the 3R,4S stereochemistry of 2-azetidinones derived from D-glyceraldehyde. For an experimental study on the synthesis of 2-azetidinones derived from D- and L-glyceraldehyde acetonide imines, see: (e) Niu, Ch.; Miller, M. J. Tetrahedron Lett. 1995, 36, 497. (f) Hubschwerlen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (g) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (h) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227 and references therein.
100. Alcaide, B.; Esteban, G.; Martín-Cantalejo, Y.; Plumet, J.; Rodríguez-López, J.; Monge, A.; Pérez-García, V. J. Org. Chem. 1994, 59, 7994.
101. β-Lactam aldehydes 8 were obtained and used for Wittig olefination as mixtures with their methoxyhemiacetals. However, these mixtures can be easily transformed to the free aldehydes by azeotropic distillation using a Dean-Stark apparatus.
102. Corey, E. J.; Snider, D. B. J. Am. Chem. Soc. 1972, 94, 2459.
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105. Other apparently more staightforward methods, i.e., the Staudinger reaction between pentynoyl chloride and the imine derived from p-anisidine and cinnamaldehyde, failed to produce the corresponding β-lactam 5a.
106. It is notable that radical cyclization to give bicyclic compounds 11-13 occurs under standard conditions, whereas related processes developed to prepare bicyclic β-lactams do not occur except in high dilution conditions. See, for example ref 9. In our case, good yields of products were obtained even when working in the absence of solvent (neat conditions).
107. 1.5 = 8.0-8.7 Hz. Therefore, the relative configuration at C1 could not be unambiguously established from NMR data.
108. (a) Angehrn, P.; Gubernator, K.; Gutknecht, E. M.; Heinze-Krauss, I.; Hubschwerlen, C.; Kania, M.; Page, M. G. P.; Specklin, J. L. 35th Intescienee Conference on Antimicrobial Agents and Chemotherapy; Program and Abstracts, F147, 1995.
109. (b) Charnas, R.; Gubernator, K.; Heinze, I.; Hubschwerlen, C. Eur. Pat. 0508234A2, 1992.
110. For the related free radical cycloisomerization of alkynetethered oxime ethers, see: (a) Marco-Contelles, J. L.; Destabel, Ch.; Gallego, P.; Chiara, J. L.; Bernabé, M. J. Org. Chem. 1986, 61, 1354. (b) Booth, S. E.; Jenkins, P. R; Swain, C. J.; Sweeney, J. B. J. Chem. Soc., Perkin Trans. 1 1994, 3499. (c) Enholm, E. J.; Burroff, J. A.; Jaramillo, L. M. Tetrahedron Lett. 1990, 31, 3927.
111. For the related free radical cycloisomerization of alkynetethered oxime ethers, see: (a) Marco-Contelles, J. L.; Destabel, Ch.; Gallego, P.; Chiara, J. L.; Bernabé, M. J. Org. Chem. 1986, 61, 1354. (b) Booth, S. E.; Jenkins, P. R; Swain, C. J.; Sweeney, J. B. J. Chem. Soc., Perkin Trans. 1 1994, 3499. (c) Enholm, E. J.; Burroff, J. A.; Jaramillo, L. M. Tetrahedron Lett. 1990, 31, 3927.
112. For the related free radical cycloisomerization of alkynetethered oxime ethers, see: (a) Marco-Contelles, J. L.; Destabel, Ch.; Gallego, P.; Chiara, J. L.; Bernabé, M. J. Org. Chem. 1986, 61, 1354. (b) Booth, S. E.; Jenkins, P. R; Swain, C. J.; Sweeney, J. B. J. Chem. Soc., Perkin Trans. 1 1994, 3499. (c) Enholm, E. J.; Burroff, J. A.; Jaramillo, L. M. Tetrahedron Lett. 1990, 31, 3927.
113. For a related ionic C3-C4 ring fragmentation, see: Alcaide, B.; Martín-Cantalejo, Y.; Rodríuez-López, J.; Sierra, M. A. J. Org. Chem. 1993, 58, 4767-4770.
114. See, for example: (a) Crimmings, M. T.; Huang, S.; Guise-Zabacki, L. E. Tetrahedron Lett. 1996, 37, 6519. (b) Horwell, D. C.; Morrell, A. I.; Roberts, E. Tetrahedron Lett, 1995, 36, 459-460 and references therein.
115. See, for example: (a) Crimmings, M. T.; Huang, S.; Guise- Zabacki, L. E. Tetrahedron Lett. 1996, 37, 6519. (b) Horwell, D. C.; Morrell, A. I.; Roberts, E. Tetrahedron Lett, 1995, 36, 459-460 and references therein.
116. For related examples on translocation of radical sites by intramolecular 1,5-hydrogen atom transfer, see: (a) Curran, D. P.; Kim, D.; Liu, H.; Shen, W. J. Am. Chem. Soc. 1988, 110, 5900. (b) Snieckus, V.; Cuevas, J.-C.; Sloan, C. P.; Liu, H.; Curran, D. J. Am. Chem. Soc. 1990, 112, 896. (c) Burke, S.; Jung, K. W. Tetrahedron Lett. 1994, 35, 5837. (d) Parsons, P. J.; Caddick, S. Tetrahedron 1994, 50, 13523.
117. For related examples on translocation of radical sites by intramolecular 1,5-hydrogen atom transfer, see: (a) Curran, D. P.; Kim, D.; Liu, H.; Shen, W. J. Am. Chem. Soc. 1988, 110, 5900. (b) Snieckus, V.; Cuevas, J.-C.; Sloan, C. P.; Liu, H.; Curran, D. J. Am. Chem. Soc. 1990, 112, 896. (c) Burke, S.; Jung, K. W. Tetrahedron Lett. 1994, 35, 5837. (d) Parsons, P. J.; Caddick, S. Tetrahedron 1994, 50, 13523.
118. For related examples on translocation of radical sites by intramolecular 1,5-hydrogen atom transfer, see: (a) Curran, D. P.; Kim, D.; Liu, H.; Shen, W. J. Am. Chem. Soc. 1988, 110, 5900. (b) Snieckus, V.; Cuevas, J.-C.; Sloan, C. P.; Liu, H.; Curran, D. J. Am. Chem. Soc. 1990, 112, 896. (c) Burke, S.; Jung, K. W. Tetrahedron Lett. 1994, 35, 5837. (d) Parsons, P. J.; Caddick, S. Tetrahedron 1994, 50, 13523.
119. For related examples on translocation of radical sites by intramolecular 1,5-hydrogen atom transfer, see: (a) Curran, D. P.; Kim, D.; Liu, H.; Shen, W. J. Am. Chem. Soc. 1988, 110, 5900. (b) Snieckus, V.; Cuevas, J.-C.; Sloan, C. P.; Liu, H.; Curran, D. J. Am. Chem. Soc. 1990, 112, 896. (c) Burke, S.; Jung, K. W. Tetrahedron Lett. 1994, 35, 5837. (d) Parsons, P. J.; Caddick, S. Tetrahedron 1994, 50, 13523.
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131. Full spectroscopic and analytical data for compounds not included in this Experimental Section are described in the Supporting Information.