Hetero [6+3] cycloaddition of fulvenes with N-alkylidene glycine esters: A facile synthesis of the delavayine and incarvillateine framework

Organic Letters

Volumn 5, Issue 10, 2003, Pages 1689-1692

  Hong, Bor Cherng ^a   Gupta, Arun Kumar ^a   Wu, Ming Fun ^a   Liao, Ju Hsiou ^a   Lee, Gene Hsiang ^b  

^a NATIONAL CHUNG CHENG UNIVERSITY   (Taiwan)

^b NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ESTER DERIVATIVE; PYRIDINE DERIVATIVE;

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

EID: 0141741220     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034329b     Document Type: Article

References (56)

1. For a recent review on fulvene chemistry, see: Neuenschwander, M. In Chemistry of Double-Bonded Functional Groups; Patai, S., Ed.; Wiley: Chichester, UK, 1989; Vol. 2, p 1131.
2. (a) Rawson, D. I.; Carpenter, B. K.; Hoffmann, H. R. J. Am. Chem. Soc. 1979, 101, 1786.
3. (b) Noyori, R.; Hayakawa, Y.; Takaya, H.; Murai, S.; Kobayashi, R.; Sonoda, N. J. Am. Chem. Soc. 1978, 100, 1759.
4. Imafuku, K.; Arai, K. Synthesis 1989, 501. Paquette, L. A.; Colapret, J. A.; Andrews, D. R. J. Org. Chem. 1985, 50, 201. Paquette, L. A.; Colapret, J. A.; Andrews, D. R. J. Org. Chem. 1985, 50, 201.
5. Imafuku, K.; Arai, K. Synthesis 1989, 501. Paquette, L. A.; Colapret, J. A.; Andrews, D. R. J. Org. Chem. 1985, 50, 201. Paquette, L. A.; Colapret, J. A.; Andrews, D. R. J. Org. Chem. 1985, 50, 201.
6. (a) Harre, M.; Raddatz, P.; Walenta, R.; Winterfeldt, E. Angew. Chem., Int. Ed. Engl. 1982, 21, 480.
7. (b) Gleiter, R.; Borzyk, O. Angew. Chem., Int. Ed. Engl. 1995, 34, 1001.
8. (a) Himeda, Y.; Yamataka, H.; Ueda, I.; Hatanaka, M. J. Org. Chem. 1997, 62, 6529.
9. (b) Nair, V.; Nair, A. G.; Radhakrishnan, K. V.; Nadakumar, M. V.; Rath, N. P. Synlett 1997, 767.
10. (a) Gupta, Y. N.; Doa, M. J.; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 7336-7338.
11. (b) Yoshida, Z.-I.; Shibata,M.; Ogino, E.; Sugimoto, T. Angew. Chem., Int. Ed. Engl. 1985, 24, 60.
12. (a) For an example of intermolecular [6+2] cycloaddition, see: Hong, B. C.; Shr, Y. J.; Wu, J. L.; Gupta, A. K.; Lin, K. J. Org. Lett. 2002, 4, 2249-2252.
13. (b) For an example of intramolecular [6+2] cycloaddition, see: Suda, M.; Hafner, K. Tetrahedron Lett. 1977, 2453. Wu, T. C.; Houk, K. N. J. Am. Chem. Soc. 1985, 107, 5308. Wu, T. C.; Houk, K. N. J. Am. Chem. Soc. 1985, 107, 5308.
14. (b) For an example of intramolecular [6+2] cycloaddition, see: Suda, M.; Hafner, K. Tetrahedron Lett. 1977, 2453. Wu, T. C.; Houk, K. N. J. Am. Chem. Soc. 1985, 107, 5308. Wu, T. C.; Houk, K. N. J. Am. Chem. Soc. 1985, 107, 5308.
15. Hong, B.-C.; Sun, S.-S.; Tsai, Y.-C. J. Org. Chem. 1997, 62, 7717.
16. For a recent review on the synthesis of indan systems, see: Hong, B.-C.; Sarshar, S. Org. Prep. Proced. Int. 1999, 31, 1.
17. Barluenga, J.; Martinez, S.; Suárez-Sobrino, A. L.; Tomás, M. J. Am. Chem. Soc. 2001, 123, 11113-11114.
18. Hong, B.-C.; Chen, Z.-Y.; Chen, W.-H. Org. Lett. 2000, 2, 2647-2649.
19. For previous papers in this series, see: (a) Hong, B.-C.; Shr, Y.-J.; Liao, J.-H. Org. Lett. 2002, 4, 663-666. (b) Hong, B.-C.; Shen, I.-C.; Liao, J.-H. Tetrahedron Lett. 2001, 42, 935-938. (c) Hong, B.-C.; Jiang, Y.-F.; Kumar, E. S. Bioorg. Med. Chem. Lett. 2001, 11, 1981-1984. (d) Hong, B.-C.; Sun, H.-I.; Chen, Z.-Y. Chem. Commun. 1999, 2125. (e) Hong, B.-C.; Chen, Z.-Y.; Kumar, E. S. J. Chem. Soc, Perkin Trans. 1 1999, 1135. (f) Hong, B.-C.; Hong, J.-H. Tetrahedron Lett. 1997, 38, 255. (g) Hong, B.-C.; Sun, S.-S.; Tsai, Y.-C. J. Org. Chem. 1997, 62, 7717.
20. For previous papers in this series, see: (a) Hong, B.-C.; Shr, Y.-J.; Liao, J.-H. Org. Lett. 2002, 4, 663-666. (b) Hong, B.-C.; Shen, I.-C.; Liao, J.-H. Tetrahedron Lett. 2001, 42, 935-938. (c) Hong, B.-C.; Jiang, Y.-F.; Kumar, E. S. Bioorg. Med. Chem. Lett. 2001, 11, 1981-1984. (d) Hong, B.-C.; Sun, H.-I.; Chen, Z.-Y. Chem. Commun. 1999, 2125. (e) Hong, B.-C.; Chen, Z.-Y.; Kumar, E. S. J. Chem. Soc, Perkin Trans. 1 1999, 1135. (f) Hong, B.-C.; Hong, J.-H. Tetrahedron Lett. 1997, 38, 255. (g) Hong, B.-C.; Sun, S.-S.; Tsai, Y.-C. J. Org. Chem. 1997, 62, 7717.
21. For previous papers in this series, see: (a) Hong, B.-C.; Shr, Y.-J.; Liao, J.-H. Org. Lett. 2002, 4, 663-666. (b) Hong, B.-C.; Shen, I.-C.; Liao, J.-H. Tetrahedron Lett. 2001, 42, 935-938. (c) Hong, B.-C.; Jiang, Y.-F.; Kumar, E. S. Bioorg. Med. Chem. Lett. 2001, 11, 1981-1984. (d) Hong, B.-C.; Sun, H.-I.; Chen, Z.-Y. Chem. Commun. 1999, 2125. (e) Hong, B.-C.; Chen, Z.-Y.; Kumar, E. S. J. Chem. Soc, Perkin Trans. 1 1999, 1135. (f) Hong, B.-C.; Hong, J.-H. Tetrahedron Lett. 1997, 38, 255. (g) Hong, B.-C.; Sun, S.-S.; Tsai, Y.-C. J. Org. Chem. 1997, 62, 7717.
22. For previous papers in this series, see: (a) Hong, B.-C.; Shr, Y.-J.; Liao, J.-H. Org. Lett. 2002, 4, 663-666. (b) Hong, B.-C.; Shen, I.-C.; Liao, J.-H. Tetrahedron Lett. 2001, 42, 935-938. (c) Hong, B.-C.; Jiang, Y.-F.; Kumar, E. S. Bioorg. Med. Chem. Lett. 2001, 11, 1981-1984. (d) Hong, B.-C.; Sun, H.-I.; Chen, Z.-Y. Chem. Commun. 1999, 2125. (e) Hong, B.-C.; Chen, Z.-Y.; Kumar, E. S. J. Chem. Soc, Perkin Trans. 1 1999, 1135. (f) Hong, B.-C.; Hong, J.-H. Tetrahedron Lett. 1997, 38, 255. (g) Hong, B.-C.; Sun, S.-S.; Tsai, Y.-C. J. Org. Chem. 1997, 62, 7717.
23. For previous papers in this series, see: (a) Hong, B.-C.; Shr, Y.-J.; Liao, J.-H. Org. Lett. 2002, 4, 663-666. (b) Hong, B.-C.; Shen, I.-C.; Liao, J.-H. Tetrahedron Lett. 2001, 42, 935-938. (c) Hong, B.-C.; Jiang, Y.-F.; Kumar, E. S. Bioorg. Med. Chem. Lett. 2001, 11, 1981-1984. (d) Hong, B.-C.; Sun, H.-I.; Chen, Z.-Y. Chem. Commun. 1999, 2125. (e) Hong, B.-C.; Chen, Z.-Y.; Kumar, E. S. J. Chem. Soc, Perkin Trans. 1 1999, 1135. (f) Hong, B.-C.; Hong, J.-H. Tetrahedron Lett. 1997, 38, 255. (g) Hong, B.-C.; Sun, S.-S.; Tsai, Y.-C. J. Org. Chem. 1997, 62, 7717.
24. For previous papers in this series, see: (a) Hong, B.-C.; Shr, Y.-J.; Liao, J.-H. Org. Lett. 2002, 4, 663-666. (b) Hong, B.-C.; Shen, I.-C.; Liao, J.-H. Tetrahedron Lett. 2001, 42, 935-938. (c) Hong, B.-C.; Jiang, Y.-F.; Kumar, E. S. Bioorg. Med. Chem. Lett. 2001, 11, 1981-1984. (d) Hong, B.-C.; Sun, H.-I.; Chen, Z.-Y. Chem. Commun. 1999, 2125. (e) Hong, B.-C.; Chen, Z.-Y.; Kumar, E. S. J. Chem. Soc, Perkin Trans. 1 1999, 1135. (f) Hong, B.-C.; Hong, J.-H. Tetrahedron Lett. 1997, 38, 255. (g) Hong, B.-C.; Sun, S.-S.; Tsai, Y.-C. J. Org. Chem. 1997, 62, 7717.
25. For previous papers in this series, see: (a) Hong, B.-C.; Shr, Y.-J.; Liao, J.-H. Org. Lett. 2002, 4, 663-666. (b) Hong, B.-C.; Shen, I.-C.; Liao, J.-H. Tetrahedron Lett. 2001, 42, 935-938. (c) Hong, B.-C.; Jiang, Y.-F.; Kumar, E. S. Bioorg. Med. Chem. Lett. 2001, 11, 1981-1984. (d) Hong, B.-C.; Sun, H.-I.; Chen, Z.-Y. Chem. Commun. 1999, 2125. (e) Hong, B.-C.; Chen, Z.-Y.; Kumar, E. S. J. Chem. Soc, Perkin Trans. 1 1999, 1135. (f) Hong, B.-C.; Hong, J.-H. Tetrahedron Lett. 1997, 38, 255. (g) Hong, B.-C.; Sun, S.-S.; Tsai, Y.-C. J. Org. Chem. 1997, 62, 7717.
26. Nakamura, M.; Kido, K.; Kinjo, J.; Nohara, T. Phytochemistry 2000, 53, 253-256.
27. Stefanska, A. L.; Cassels, R.; Ready, S. J.; Warr, S. R. J. Antibiot. 2000, 53, 357-363.
28. Nakamura, M.; Chi, Y.-M.; Yan, W.-M.; Yonezawa, A.; Nakasugi, Yumiko; Y., Toyokichi; Hashimoto, F.; Kinjo, J.; Nohara, T.; Sakurada, S. Planta Med. 2001, 67, 114-117.
29. Sunazuka, T.; Zhi-Ming, T.; Harigaya, Y.; Takamatsu, S.; Hayashi, M. J. Antibiot. 1997, 50, 274-275.
30. Skaltsounis, A.-L.; Michel, S.; Tillequin, F.; Koch, M.; Pusset, J.; Chauviere, G. Helv. Chim. Acta 1985, 68, 1679-1685.
31. (a) Cook, C. E.; Wani, M. C.; Jump, J. M.; Lee, Y.-W.; Fail, P. A. J. Med. Chem. 1995, 38, 753-763.
32. (b) Jump, J. M.; McPhail, A. T. Cook, C. E. Tetrahedron Lett. 1997, 38, 3691-3694.
33. The method represents an efficient and convergent method for the construction of the pyrrolidine structure unit, see: (a) Wilson, N. S.; Sarko, C. R.; Roth, G. P. Tetrahedron Lett. 2001, 42, 8939-8942. (b) Abellán, T.; Mancheño, B.; Nájera, C.; Sansano, J. Tetrahedron 2001, 57, 6627-6640. (c) Casas, J.; Grigg, R.; Najera, C.; Sansano, J. M. Eur. J. Org. Chem. 2001, 10, 1971-1982. (d) Subramaniyan, G.; Raghunathan, R. Tetrahedron 2001, 57, 2909-2916. (e) Grigg, R.; Liu, A.; Shaw, D.; Suganthan, S.; Washington, M. L.; Woodall, D. E.; Yoganathan, G. Tetrahedron Lett. 2000, 41, 7129-7134. (f) Nyerges, M.; Fejes, I.; Toeke, L. Tetrahedron Lett. 2000, 41, 7951-7954. (g) Vivanco, S.; Lecea, B.; Arrieta, A.; Prieto, P.; Morao, I.; Linden, A.; Cossio, F. P. J. Am. Chem. Soc. 2000, 122, 6078-6092. (h) Dondas, H. A.; Duraisingham, J.; Grigg, R.; MacLachlan, W. S.; MacPherson, D. T.; Thornton-Pett, M.; Sridharan, V.; Suganthan, S. Tetrahedron 2000, 56, 4063-4070. (i) Fejes, I.; Toke, L.; Nyerges, M.; Pak, C. S. Tetrahedron 2000, 56, 639-644. (j) Fejes, I.; Toke, L.; Blasko, G.; Nyerges, M.; Pak, C. S. Tetrahedron 2000, 56, 8545-8554. (k) Gong, Y.-D.; Najdi, S.; Olmstead, M. M.; Kurth, M. J. J. Org. Chem. 1998, 63, 3081-3086. (1) Pejes, I.; Nyerges, M.; Szoellosy, A.; Blasko, G.; Toke, L. Tetrahedron 2001, 57, 1129-1138. (m) Nyerges, M.; Gajdics, L.; Szoelloesy, A.; Toeke, L. Synlett 1999, 1, 111-113.
34. The method represents an efficient and convergent method for the construction of the pyrrolidine structure unit, see: (a) Wilson, N. S.; Sarko, C. R.; Roth, G. P. Tetrahedron Lett. 2001, 42, 8939-8942. (b) Abellán, T.; Mancheño, B.; Nájera, C.; Sansano, J. Tetrahedron 2001, 57, 6627-6640. (c) Casas, J.; Grigg, R.; Najera, C.; Sansano, J. M. Eur. J. Org. Chem. 2001, 10, 1971-1982. (d) Subramaniyan, G.; Raghunathan, R. Tetrahedron 2001, 57, 2909-2916. (e) Grigg, R.; Liu, A.; Shaw, D.; Suganthan, S.; Washington, M. L.; Woodall, D. E.; Yoganathan, G. Tetrahedron Lett. 2000, 41, 7129-7134. (f) Nyerges, M.; Fejes, I.; Toeke, L. Tetrahedron Lett. 2000, 41, 7951-7954. (g) Vivanco, S.; Lecea, B.; Arrieta, A.; Prieto, P.; Morao, I.; Linden, A.; Cossio, F. P. J. Am. Chem. Soc. 2000, 122, 6078-6092. (h) Dondas, H. A.; Duraisingham, J.; Grigg, R.; MacLachlan, W. S.; MacPherson, D. T.; Thornton-Pett, M.; Sridharan, V.; Suganthan, S. Tetrahedron 2000, 56, 4063-4070. (i) Fejes, I.; Toke, L.; Nyerges, M.; Pak, C. S. Tetrahedron 2000, 56, 639-644. (j) Fejes, I.; Toke, L.; Blasko, G.; Nyerges, M.; Pak, C. S. Tetrahedron 2000, 56, 8545-8554. (k) Gong, Y.-D.; Najdi, S.; Olmstead, M. M.; Kurth, M. J. J. Org. Chem. 1998, 63, 3081-3086. (1) Pejes, I.; Nyerges, M.; Szoellosy, A.; Blasko, G.; Toke, L. Tetrahedron 2001, 57, 1129-1138. (m) Nyerges, M.; Gajdics, L.; Szoelloesy, A.; Toeke, L. Synlett 1999, 1, 111-113.
35. The method represents an efficient and convergent method for the construction of the pyrrolidine structure unit, see: (a) Wilson, N. S.; Sarko, C. R.; Roth, G. P. Tetrahedron Lett. 2001, 42, 8939-8942. (b) Abellán, T.; Mancheño, B.; Nájera, C.; Sansano, J. Tetrahedron 2001, 57, 6627-6640. (c) Casas, J.; Grigg, R.; Najera, C.; Sansano, J. M. Eur. J. Org. Chem. 2001, 10, 1971-1982. (d) Subramaniyan, G.; Raghunathan, R. Tetrahedron 2001, 57, 2909-2916. (e) Grigg, R.; Liu, A.; Shaw, D.; Suganthan, S.; Washington, M. L.; Woodall, D. E.; Yoganathan, G. Tetrahedron Lett. 2000, 41, 7129-7134. (f) Nyerges, M.; Fejes, I.; Toeke, L. Tetrahedron Lett. 2000, 41, 7951-7954. (g) Vivanco, S.; Lecea, B.; Arrieta, A.; Prieto, P.; Morao, I.; Linden, A.; Cossio, F. P. J. Am. Chem. Soc. 2000, 122, 6078-6092. (h) Dondas, H. A.; Duraisingham, J.; Grigg, R.; MacLachlan, W. S.; MacPherson, D. T.; Thornton-Pett, M.; Sridharan, V.; Suganthan, S. Tetrahedron 2000, 56, 4063-4070. (i) Fejes, I.; Toke, L.; Nyerges, M.; Pak, C. S. Tetrahedron 2000, 56, 639-644. (j) Fejes, I.; Toke, L.; Blasko, G.; Nyerges, M.; Pak, C. S. Tetrahedron 2000, 56, 8545-8554. (k) Gong, Y.-D.; Najdi, S.; Olmstead, M. M.; Kurth, M. J. J. Org. Chem. 1998, 63, 3081-3086. (1) Pejes, I.; Nyerges, M.; Szoellosy, A.; Blasko, G.; Toke, L. Tetrahedron 2001, 57, 1129-1138. (m) Nyerges, M.; Gajdics, L.; Szoelloesy, A.; Toeke, L. Synlett 1999, 1, 111-113.
36. The method represents an efficient and convergent method for the construction of the pyrrolidine structure unit, see: (a) Wilson, N. S.; Sarko, C. R.; Roth, G. P. Tetrahedron Lett. 2001, 42, 8939-8942. (b) Abellán, T.; Mancheño, B.; Nájera, C.; Sansano, J. Tetrahedron 2001, 57, 6627-6640. (c) Casas, J.; Grigg, R.; Najera, C.; Sansano, J. M. Eur. J. Org. Chem. 2001, 10, 1971-1982. (d) Subramaniyan, G.; Raghunathan, R. Tetrahedron 2001, 57, 2909-2916. (e) Grigg, R.; Liu, A.; Shaw, D.; Suganthan, S.; Washington, M. L.; Woodall, D. E.; Yoganathan, G. Tetrahedron Lett. 2000, 41, 7129-7134. (f) Nyerges, M.; Fejes, I.; Toeke, L. Tetrahedron Lett. 2000, 41, 7951-7954. (g) Vivanco, S.; Lecea, B.; Arrieta, A.; Prieto, P.; Morao, I.; Linden, A.; Cossio, F. P. J. Am. Chem. Soc. 2000, 122, 6078-6092. (h) Dondas, H. A.; Duraisingham, J.; Grigg, R.; MacLachlan, W. S.; MacPherson, D. T.; Thornton-Pett, M.; Sridharan, V.; Suganthan, S. Tetrahedron 2000, 56, 4063-4070. (i) Fejes, I.; Toke, L.; Nyerges, M.; Pak, C. S. Tetrahedron 2000, 56, 639-644. (j) Fejes, I.; Toke, L.; Blasko, G.; Nyerges, M.; Pak, C. S. Tetrahedron 2000, 56, 8545-8554. (k) Gong, Y.-D.; Najdi, S.; Olmstead, M. M.; Kurth, M. J. J. Org. Chem. 1998, 63, 3081-3086. (1) Pejes, I.; Nyerges, M.; Szoellosy, A.; Blasko, G.; Toke, L. Tetrahedron 2001, 57, 1129-1138. (m) Nyerges, M.; Gajdics, L.; Szoelloesy, A.; Toeke, L. Synlett 1999, 1, 111-113.
37. The method represents an efficient and convergent method for the construction of the pyrrolidine structure unit, see: (a) Wilson, N. S.; Sarko, C. R.; Roth, G. P. Tetrahedron Lett. 2001, 42, 8939-8942. (b) Abellán, T.; Mancheño, B.; Nájera, C.; Sansano, J. Tetrahedron 2001, 57, 6627-6640. (c) Casas, J.; Grigg, R.; Najera, C.; Sansano, J. M. Eur. J. Org. Chem. 2001, 10, 1971-1982. (d) Subramaniyan, G.; Raghunathan, R. Tetrahedron 2001, 57, 2909-2916. (e) Grigg, R.; Liu, A.; Shaw, D.; Suganthan, S.; Washington, M. L.; Woodall, D. E.; Yoganathan, G. Tetrahedron Lett. 2000, 41, 7129-7134. (f) Nyerges, M.; Fejes, I.; Toeke, L. Tetrahedron Lett. 2000, 41, 7951-7954. (g) Vivanco, S.; Lecea, B.; Arrieta, A.; Prieto, P.; Morao, I.; Linden, A.; Cossio, F. P. J. Am. Chem. Soc. 2000, 122, 6078-6092. (h) Dondas, H. A.; Duraisingham, J.; Grigg, R.; MacLachlan, W. S.; MacPherson, D. T.; Thornton-Pett, M.; Sridharan, V.; Suganthan, S. Tetrahedron 2000, 56, 4063-4070. (i) Fejes, I.; Toke, L.; Nyerges, M.; Pak, C. S. Tetrahedron 2000, 56, 639-644. (j) Fejes, I.; Toke, L.; Blasko, G.; Nyerges, M.; Pak, C. S. Tetrahedron 2000, 56, 8545-8554. (k) Gong, Y.-D.; Najdi, S.; Olmstead, M. M.; Kurth, M. J. J. Org. Chem. 1998, 63, 3081-3086. (1) Pejes, I.; Nyerges, M.; Szoellosy, A.; Blasko, G.; Toke, L. Tetrahedron 2001, 57, 1129-1138. (m) Nyerges, M.; Gajdics, L.; Szoelloesy, A.; Toeke, L. Synlett 1999, 1, 111-113.
38. The method represents an efficient and convergent method for the construction of the pyrrolidine structure unit, see: (a) Wilson, N. S.; Sarko, C. R.; Roth, G. P. Tetrahedron Lett. 2001, 42, 8939-8942. (b) Abellán, T.; Mancheño, B.; Nájera, C.; Sansano, J. Tetrahedron 2001, 57, 6627-6640. (c) Casas, J.; Grigg, R.; Najera, C.; Sansano, J. M. Eur. J. Org. Chem. 2001, 10, 1971-1982. (d) Subramaniyan, G.; Raghunathan, R. Tetrahedron 2001, 57, 2909-2916. (e) Grigg, R.; Liu, A.; Shaw, D.; Suganthan, S.; Washington, M. L.; Woodall, D. E.; Yoganathan, G. Tetrahedron Lett. 2000, 41, 7129-7134. (f) Nyerges, M.; Fejes, I.; Toeke, L. Tetrahedron Lett. 2000, 41, 7951-7954. (g) Vivanco, S.; Lecea, B.; Arrieta, A.; Prieto, P.; Morao, I.; Linden, A.; Cossio, F. P. J. Am. Chem. Soc. 2000, 122, 6078-6092. (h) Dondas, H. A.; Duraisingham, J.; Grigg, R.; MacLachlan, W. S.; MacPherson, D. T.; Thornton-Pett, M.; Sridharan, V.; Suganthan, S. Tetrahedron 2000, 56, 4063-4070. (i) Fejes, I.; Toke, L.; Nyerges, M.; Pak, C. S. Tetrahedron 2000, 56, 639-644. (j) Fejes, I.; Toke, L.; Blasko, G.; Nyerges, M.; Pak, C. S. Tetrahedron 2000, 56, 8545-8554. (k) Gong, Y.-D.; Najdi, S.; Olmstead, M. M.; Kurth, M. J. J. Org. Chem. 1998, 63, 3081-3086. (1) Pejes, I.; Nyerges, M.; Szoellosy, A.; Blasko, G.; Toke, L. Tetrahedron 2001, 57, 1129-1138. (m) Nyerges, M.; Gajdics, L.; Szoelloesy, A.; Toeke, L. Synlett 1999, 1, 111-113.
39. The method represents an efficient and convergent method for the construction of the pyrrolidine structure unit, see: (a) Wilson, N. S.; Sarko, C. R.; Roth, G. P. Tetrahedron Lett. 2001, 42, 8939-8942. (b) Abellán, T.; Mancheño, B.; Nájera, C.; Sansano, J. Tetrahedron 2001, 57, 6627-6640. (c) Casas, J.; Grigg, R.; Najera, C.; Sansano, J. M. Eur. J. Org. Chem. 2001, 10, 1971-1982. (d) Subramaniyan, G.; Raghunathan, R. Tetrahedron 2001, 57, 2909-2916. (e) Grigg, R.; Liu, A.; Shaw, D.; Suganthan, S.; Washington, M. L.; Woodall, D. E.; Yoganathan, G. Tetrahedron Lett. 2000, 41, 7129-7134. (f) Nyerges, M.; Fejes, I.; Toeke, L. Tetrahedron Lett. 2000, 41, 7951-7954. (g) Vivanco, S.; Lecea, B.; Arrieta, A.; Prieto, P.; Morao, I.; Linden, A.; Cossio, F. P. J. Am. Chem. Soc. 2000, 122, 6078-6092. (h) Dondas, H. A.; Duraisingham, J.; Grigg, R.; MacLachlan, W. S.; MacPherson, D. T.; Thornton-Pett, M.; Sridharan, V.; Suganthan, S. Tetrahedron 2000, 56, 4063-4070. (i) Fejes, I.; Toke, L.; Nyerges, M.; Pak, C. S. Tetrahedron 2000, 56, 639-644. (j) Fejes, I.; Toke, L.; Blasko, G.; Nyerges, M.; Pak, C. S. Tetrahedron 2000, 56, 8545-8554. (k) Gong, Y.-D.; Najdi, S.; Olmstead, M. M.; Kurth, M. J. J. Org. Chem. 1998, 63, 3081-3086. (1) Pejes, I.; Nyerges, M.; Szoellosy, A.; Blasko, G.; Toke, L. Tetrahedron 2001, 57, 1129-1138. (m) Nyerges, M.; Gajdics, L.; Szoelloesy, A.; Toeke, L. Synlett 1999, 1, 111-113.
40. The method represents an efficient and convergent method for the construction of the pyrrolidine structure unit, see: (a) Wilson, N. S.; Sarko, C. R.; Roth, G. P. Tetrahedron Lett. 2001, 42, 8939-8942. (b) Abellán, T.; Mancheño, B.; Nájera, C.; Sansano, J. Tetrahedron 2001, 57, 6627-6640. (c) Casas, J.; Grigg, R.; Najera, C.; Sansano, J. M. Eur. J. Org. Chem. 2001, 10, 1971-1982. (d) Subramaniyan, G.; Raghunathan, R. Tetrahedron 2001, 57, 2909-2916. (e) Grigg, R.; Liu, A.; Shaw, D.; Suganthan, S.; Washington, M. L.; Woodall, D. E.; Yoganathan, G. Tetrahedron Lett. 2000, 41, 7129-7134. (f) Nyerges, M.; Fejes, I.; Toeke, L. Tetrahedron Lett. 2000, 41, 7951-7954. (g) Vivanco, S.; Lecea, B.; Arrieta, A.; Prieto, P.; Morao, I.; Linden, A.; Cossio, F. P. J. Am. Chem. Soc. 2000, 122, 6078-6092. (h) Dondas, H. A.; Duraisingham, J.; Grigg, R.; MacLachlan, W. S.; MacPherson, D. T.; Thornton-Pett, M.; Sridharan, V.; Suganthan, S. Tetrahedron 2000, 56, 4063-4070. (i) Fejes, I.; Toke, L.; Nyerges, M.; Pak, C. S. Tetrahedron 2000, 56, 639-644. (j) Fejes, I.; Toke, L.; Blasko, G.; Nyerges, M.; Pak, C. S. Tetrahedron 2000, 56, 8545-8554. (k) Gong, Y.-D.; Najdi, S.; Olmstead, M. M.; Kurth, M. J. J. Org. Chem. 1998, 63, 3081-3086. (1) Pejes, I.; Nyerges, M.; Szoellosy, A.; Blasko, G.; Toke, L. Tetrahedron 2001, 57, 1129-1138. (m) Nyerges, M.; Gajdics, L.; Szoelloesy, A.; Toeke, L. Synlett 1999, 1, 111-113.
41. The method represents an efficient and convergent method for the construction of the pyrrolidine structure unit, see: (a) Wilson, N. S.; Sarko, C. R.; Roth, G. P. Tetrahedron Lett. 2001, 42, 8939-8942. (b) Abellán, T.; Mancheño, B.; Nájera, C.; Sansano, J. Tetrahedron 2001, 57, 6627-6640. (c) Casas, J.; Grigg, R.; Najera, C.; Sansano, J. M. Eur. J. Org. Chem. 2001, 10, 1971-1982. (d) Subramaniyan, G.; Raghunathan, R. Tetrahedron 2001, 57, 2909-2916. (e) Grigg, R.; Liu, A.; Shaw, D.; Suganthan, S.; Washington, M. L.; Woodall, D. E.; Yoganathan, G. Tetrahedron Lett. 2000, 41, 7129-7134. (f) Nyerges, M.; Fejes, I.; Toeke, L. Tetrahedron Lett. 2000, 41, 7951-7954. (g) Vivanco, S.; Lecea, B.; Arrieta, A.; Prieto, P.; Morao, I.; Linden, A.; Cossio, F. P. J. Am. Chem. Soc. 2000, 122, 6078-6092. (h) Dondas, H. A.; Duraisingham, J.; Grigg, R.; MacLachlan, W. S.; MacPherson, D. T.; Thornton-Pett, M.; Sridharan, V.; Suganthan, S. Tetrahedron 2000, 56, 4063-4070. (i) Fejes, I.; Toke, L.; Nyerges, M.; Pak, C. S. Tetrahedron 2000, 56, 639-644. (j) Fejes, I.; Toke, L.; Blasko, G.; Nyerges, M.; Pak, C. S. Tetrahedron 2000, 56, 8545-8554. (k) Gong, Y.-D.; Najdi, S.; Olmstead, M. M.; Kurth, M. J. J. Org. Chem. 1998, 63, 3081-3086. (1) Pejes, I.; Nyerges, M.; Szoellosy, A.; Blasko, G.; Toke, L. Tetrahedron 2001, 57, 1129-1138. (m) Nyerges, M.; Gajdics, L.; Szoelloesy, A.; Toeke, L. Synlett 1999, 1, 111-113.
42. The method represents an efficient and convergent method for the construction of the pyrrolidine structure unit, see: (a) Wilson, N. S.; Sarko, C. R.; Roth, G. P. Tetrahedron Lett. 2001, 42, 8939-8942. (b) Abellán, T.; Mancheño, B.; Nájera, C.; Sansano, J. Tetrahedron 2001, 57, 6627-6640. (c) Casas, J.; Grigg, R.; Najera, C.; Sansano, J. M. Eur. J. Org. Chem. 2001, 10, 1971-1982. (d) Subramaniyan, G.; Raghunathan, R. Tetrahedron 2001, 57, 2909-2916. (e) Grigg, R.; Liu, A.; Shaw, D.; Suganthan, S.; Washington, M. L.; Woodall, D. E.; Yoganathan, G. Tetrahedron Lett. 2000, 41, 7129-7134. (f) Nyerges, M.; Fejes, I.; Toeke, L. Tetrahedron Lett. 2000, 41, 7951-7954. (g) Vivanco, S.; Lecea, B.; Arrieta, A.; Prieto, P.; Morao, I.; Linden, A.; Cossio, F. P. J. Am. Chem. Soc. 2000, 122, 6078-6092. (h) Dondas, H. A.; Duraisingham, J.; Grigg, R.; MacLachlan, W. S.; MacPherson, D. T.; Thornton-Pett, M.; Sridharan, V.; Suganthan, S. Tetrahedron 2000, 56, 4063-4070. (i) Fejes, I.; Toke, L.; Nyerges, M.; Pak, C. S. Tetrahedron 2000, 56, 639-644. (j) Fejes, I.; Toke, L.; Blasko, G.; Nyerges, M.; Pak, C. S. Tetrahedron 2000, 56, 8545-8554. (k) Gong, Y.-D.; Najdi, S.; Olmstead, M. M.; Kurth, M. J. J. Org. Chem. 1998, 63, 3081-3086. (1) Pejes, I.; Nyerges, M.; Szoellosy, A.; Blasko, G.; Toke, L. Tetrahedron 2001, 57, 1129-1138. (m) Nyerges, M.; Gajdics, L.; Szoelloesy, A.; Toeke, L. Synlett 1999, 1, 111-113.
43. The method represents an efficient and convergent method for the construction of the pyrrolidine structure unit, see: (a) Wilson, N. S.; Sarko, C. R.; Roth, G. P. Tetrahedron Lett. 2001, 42, 8939-8942. (b) Abellán, T.; Mancheño, B.; Nájera, C.; Sansano, J. Tetrahedron 2001, 57, 6627-6640. (c) Casas, J.; Grigg, R.; Najera, C.; Sansano, J. M. Eur. J. Org. Chem. 2001, 10, 1971-1982. (d) Subramaniyan, G.; Raghunathan, R. Tetrahedron 2001, 57, 2909-2916. (e) Grigg, R.; Liu, A.; Shaw, D.; Suganthan, S.; Washington, M. L.; Woodall, D. E.; Yoganathan, G. Tetrahedron Lett. 2000, 41, 7129-7134. (f) Nyerges, M.; Fejes, I.; Toeke, L. Tetrahedron Lett. 2000, 41, 7951-7954. (g) Vivanco, S.; Lecea, B.; Arrieta, A.; Prieto, P.; Morao, I.; Linden, A.; Cossio, F. P. J. Am. Chem. Soc. 2000, 122, 6078-6092. (h) Dondas, H. A.; Duraisingham, J.; Grigg, R.; MacLachlan, W. S.; MacPherson, D. T.; Thornton-Pett, M.; Sridharan, V.; Suganthan, S. Tetrahedron 2000, 56, 4063-4070. (i) Fejes, I.; Toke, L.; Nyerges, M.; Pak, C. S. Tetrahedron 2000, 56, 639-644. (j) Fejes, I.; Toke, L.; Blasko, G.; Nyerges, M.; Pak, C. S. Tetrahedron 2000, 56, 8545-8554. (k) Gong, Y.-D.; Najdi, S.; Olmstead, M. M.; Kurth, M. J. J. Org. Chem. 1998, 63, 3081-3086. (1) Pejes, I.; Nyerges, M.; Szoellosy, A.; Blasko, G.; Toke, L. Tetrahedron 2001, 57, 1129-1138. (m) Nyerges, M.; Gajdics, L.; Szoelloesy, A.; Toeke, L. Synlett 1999, 1, 111-113.
44. The method represents an efficient and convergent method for the construction of the pyrrolidine structure unit, see: (a) Wilson, N. S.; Sarko, C. R.; Roth, G. P. Tetrahedron Lett. 2001, 42, 8939-8942. (b) Abellán, T.; Mancheño, B.; Nájera, C.; Sansano, J. Tetrahedron 2001, 57, 6627-6640. (c) Casas, J.; Grigg, R.; Najera, C.; Sansano, J. M. Eur. J. Org. Chem. 2001, 10, 1971-1982. (d) Subramaniyan, G.; Raghunathan, R. Tetrahedron 2001, 57, 2909-2916. (e) Grigg, R.; Liu, A.; Shaw, D.; Suganthan, S.; Washington, M. L.; Woodall, D. E.; Yoganathan, G. Tetrahedron Lett. 2000, 41, 7129-7134. (f) Nyerges, M.; Fejes, I.; Toeke, L. Tetrahedron Lett. 2000, 41, 7951-7954. (g) Vivanco, S.; Lecea, B.; Arrieta, A.; Prieto, P.; Morao, I.; Linden, A.; Cossio, F. P. J. Am. Chem. Soc. 2000, 122, 6078-6092. (h) Dondas, H. A.; Duraisingham, J.; Grigg, R.; MacLachlan, W. S.; MacPherson, D. T.; Thornton-Pett, M.; Sridharan, V.; Suganthan, S. Tetrahedron 2000, 56, 4063-4070. (i) Fejes, I.; Toke, L.; Nyerges, M.; Pak, C. S. Tetrahedron 2000, 56, 639-644. (j) Fejes, I.; Toke, L.; Blasko, G.; Nyerges, M.; Pak, C. S. Tetrahedron 2000, 56, 8545-8554. (k) Gong, Y.-D.; Najdi, S.; Olmstead, M. M.; Kurth, M. J. J. Org. Chem. 1998, 63, 3081-3086. (1) Pejes, I.; Nyerges, M.; Szoellosy, A.; Blasko, G.; Toke, L. Tetrahedron 2001, 57, 1129-1138. (m) Nyerges, M.; Gajdics, L.; Szoelloesy, A.; Toeke, L. Synlett 1999, 1, 111-113.
45. The method represents an efficient and convergent method for the construction of the pyrrolidine structure unit, see: (a) Wilson, N. S.; Sarko, C. R.; Roth, G. P. Tetrahedron Lett. 2001, 42, 8939-8942. (b) Abellán, T.; Mancheño, B.; Nájera, C.; Sansano, J. Tetrahedron 2001, 57, 6627-6640. (c) Casas, J.; Grigg, R.; Najera, C.; Sansano, J. M. Eur. J. Org. Chem. 2001, 10, 1971-1982. (d) Subramaniyan, G.; Raghunathan, R. Tetrahedron 2001, 57, 2909-2916. (e) Grigg, R.; Liu, A.; Shaw, D.; Suganthan, S.; Washington, M. L.; Woodall, D. E.; Yoganathan, G. Tetrahedron Lett. 2000, 41, 7129-7134. (f) Nyerges, M.; Fejes, I.; Toeke, L. Tetrahedron Lett. 2000, 41, 7951-7954. (g) Vivanco, S.; Lecea, B.; Arrieta, A.; Prieto, P.; Morao, I.; Linden, A.; Cossio, F. P. J. Am. Chem. Soc. 2000, 122, 6078-6092. (h) Dondas, H. A.; Duraisingham, J.; Grigg, R.; MacLachlan, W. S.; MacPherson, D. T.; Thornton-Pett, M.; Sridharan, V.; Suganthan, S. Tetrahedron 2000, 56, 4063-4070. (i) Fejes, I.; Toke, L.; Nyerges, M.; Pak, C. S. Tetrahedron 2000, 56, 639-644. (j) Fejes, I.; Toke, L.; Blasko, G.; Nyerges, M.; Pak, C. S. Tetrahedron 2000, 56, 8545-8554. (k) Gong, Y.-D.; Najdi, S.; Olmstead, M. M.; Kurth, M. J. J. Org. Chem. 1998, 63, 3081-3086. (1) Pejes, I.; Nyerges, M.; Szoellosy, A.; Blasko, G.; Toke, L. Tetrahedron 2001, 57, 1129-1138. (m) Nyerges, M.; Gajdics, L.; Szoelloesy, A.; Toeke, L. Synlett 1999, 1, 111-113.
46. (a) Dimroth, F. Chem. Ber. 1957, 90, 1628-1633.
47. (b) Dallacker, F. Justus Liebigs Ann. Chem. 1961, 643, 82-90.
48. (c) Waly, M. A. Boll. Chim. Farm. 2000, 139, 217-221.
49. Dell, C. P. J. Chem. Soc., Perkin Trans. 1 1998, 3873-3905.
50. For a review on N-metalated azomethine ylides, see: Kanemasa, S.; Tsuge, O. Adv. Cycloaddit. 1993, 3, 99-159.
51. Kato, H.; Kobayashi, T.; Ciobanu, M. Tetrahedron 1997, 53, 9921-9934.
52. Djapa, F.; Ciamala, K.; Melot, J.-M.; Vebrel, J.; Herlem, G. J. Chem. Soc., Perkin Trans. 1 2002, 687-695.
53. Nair, V.; Nandakumar, M. V.; Maliakal, D.; Mathen, J. S.; Rath, N. P. Tetrahedron 2000, 56, 8001-8005.
54. 13C NMR, DEPT, IR, MS, and HRMS. In most cases COSY and HMQC spectra were also obtained. Yields refer to spectroscopically and chromatographically homogeneous (>95%) materials.
55. 2)].
56. 2)].