A highly efficient and stereoselective synthesis of polyhydroxylated pyrrolidines via regioselective asymmetric aminohydroxylation (RAA) and intramolecular amidomercuration reactions

Synlett

Volumn , Issue 9 SPEC. ISS., 2003, Pages 1279-1282

  Singh, Satwinder ^a   Chikkanna, Dinesh ^a   Singh, Om V ^a   Han, Hyunsoo ^a  

^a UNIVERSITY OF TEXAS AT SAN ANTONIO   (United States)

Author keywords

Carbohydrate; Glycosidase inhibitor; Intramolecular amidomercuration reaction; Polyhydroxylated pyrrolidine; Regioselective asymmetric aminohydroxylation reaction

Indexed keywords

ALKENE; AMIDE; AMINOALCOHOL; PYRROLIDINE DERIVATIVE;

AMIDOMERCURATION; AMINOHYDROXYLATION; ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHIRALITY; CYCLIZATION; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; HYDROXYLATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; TECHNIQUE;

EID: 0038780840     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40347     Document Type: Article

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36. For more recent literatures for the synthesis and biological activity of I, see: (a) Donohoe, T. J.; Headley, C. E.; Cousins, R. P. C.; Cowley, A. Org. Lett. 2003, 7, 999. (b) Dondoni, A.; Giovannini, P. P.; Perrone, D. J. Org. Chem. 2002, 67, 7203. (c) Cubero, I.; Plaza Lopez-Espinosa, M. T.; Robles Diaz, R.; Franco Montalban, F. Carbohydr. Res. 2001, 330, 401. (d) Saotome, C.; Kanie, Y.; Kanie, O.; Wong, C.-H. Bioorg. Med. Chem. 2000, 8, 2249. (e) Colobert, F.; Tito, A.; Khiar, N.; Denni, D.; Medina, M. A.; Martin-Lomas, M.; Ruano, J. G.; Solladie, G. J. Org. Chem. 1998, 63, 8918. (f) Takayama, S.; Martin, R.; Wu, J.; Laslo, K.; Siuzdak, G.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 8146. (g) Huwe, C. M.; Blechert, S. Synthesis 1997, 61. (h) McCort, I.; Dureault, A.; Depezay, J.-C. Tetrahedron Lett. 1996, 37, 7717. (i) Asano, N.; Oseki, K.; Kizu, H.; Matsui, K. J. Med. Chem. 1994, 37, 3701. (j) Zou, W.; Szarek, W. A. Carbohydr. Res. 1993, 242, 311. (k) Masaki, Y.; Oda, H.; Kazuta, K.; Usai, A.; Itoh, A.; Xu, F. Tetrahedron Lett. 1992, 33, 5089. (l) Kajimoto, T.; Chen, L.; Liu, K.-C.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113, 6678. (m) Liu, K.-C.; Kajimoto, T.; Chen, L.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280. (n) Huang, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (o) Dureault, A.; Portal, M.; Depezay, J. C. Synlett 1991, 225. (p) Reitz, A. B.; Baxter, E. W. Tetrahedron Lett. 1990, 31, 6777. (q) Shing, T. K. M. Tetrahedron 1988, 44, 7261. (r) Fleet, G. W. J.; Smith, P. W. Tetrahedron 1987, 43, 971. (s) Card, P. J.; Hitz, W. D. J. Org. Chem. 1985, 50, 891.
37. For more recent literatures for the synthesis and biological activity of I, see: (a) Donohoe, T. J.; Headley, C. E.; Cousins, R. P. C.; Cowley, A. Org. Lett. 2003, 7, 999. (b) Dondoni, A.; Giovannini, P. P.; Perrone, D. J. Org. Chem. 2002, 67, 7203. (c) Cubero, I.; Plaza Lopez-Espinosa, M. T.; Robles Diaz, R.; Franco Montalban, F. Carbohydr. Res. 2001, 330, 401. (d) Saotome, C.; Kanie, Y.; Kanie, O.; Wong, C.-H. Bioorg. Med. Chem. 2000, 8, 2249. (e) Colobert, F.; Tito, A.; Khiar, N.; Denni, D.; Medina, M. A.; Martin-Lomas, M.; Ruano, J. G.; Solladie, G. J. Org. Chem. 1998, 63, 8918. (f) Takayama, S.; Martin, R.; Wu, J.; Laslo, K.; Siuzdak, G.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 8146. (g) Huwe, C. M.; Blechert, S. Synthesis 1997, 61. (h) McCort, I.; Dureault, A.; Depezay, J.-C. Tetrahedron Lett. 1996, 37, 7717. (i) Asano, N.; Oseki, K.; Kizu, H.; Matsui, K. J. Med. Chem. 1994, 37, 3701. (j) Zou, W.; Szarek, W. A. Carbohydr. Res. 1993, 242, 311. (k) Masaki, Y.; Oda, H.; Kazuta, K.; Usai, A.; Itoh, A.; Xu, F. Tetrahedron Lett. 1992, 33, 5089. (l) Kajimoto, T.; Chen, L.; Liu, K.-C.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113, 6678. (m) Liu, K.-C.; Kajimoto, T.; Chen, L.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280. (n) Huang, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (o) Dureault, A.; Portal, M.; Depezay, J. C. Synlett 1991, 225. (p) Reitz, A. B.; Baxter, E. W. Tetrahedron Lett. 1990, 31, 6777. (q) Shing, T. K. M. Tetrahedron 1988, 44, 7261. (r) Fleet, G. W. J.; Smith, P. W. Tetrahedron 1987, 43, 971. (s) Card, P. J.; Hitz, W. D. J. Org. Chem. 1985, 50, 891.
38. For more recent literatures for the synthesis and biological activity of I, see: (a) Donohoe, T. J.; Headley, C. E.; Cousins, R. P. C.; Cowley, A. Org. Lett. 2003, 7, 999. (b) Dondoni, A.; Giovannini, P. P.; Perrone, D. J. Org. Chem. 2002, 67, 7203. (c) Cubero, I.; Plaza Lopez-Espinosa, M. T.; Robles Diaz, R.; Franco Montalban, F. Carbohydr. Res. 2001, 330, 401. (d) Saotome, C.; Kanie, Y.; Kanie, O.; Wong, C.-H. Bioorg. Med. Chem. 2000, 8, 2249. (e) Colobert, F.; Tito, A.; Khiar, N.; Denni, D.; Medina, M. A.; Martin-Lomas, M.; Ruano, J. G.; Solladie, G. J. Org. Chem. 1998, 63, 8918. (f) Takayama, S.; Martin, R.; Wu, J.; Laslo, K.; Siuzdak, G.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 8146. (g) Huwe, C. M.; Blechert, S. Synthesis 1997, 61. (h) McCort, I.; Dureault, A.; Depezay, J.-C. Tetrahedron Lett. 1996, 37, 7717. (i) Asano, N.; Oseki, K.; Kizu, H.; Matsui, K. J. Med. Chem. 1994, 37, 3701. (j) Zou, W.; Szarek, W. A. Carbohydr. Res. 1993, 242, 311. (k) Masaki, Y.; Oda, H.; Kazuta, K.; Usai, A.; Itoh, A.; Xu, F. Tetrahedron Lett. 1992, 33, 5089. (l) Kajimoto, T.; Chen, L.; Liu, K.-C.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113, 6678. (m) Liu, K.-C.; Kajimoto, T.; Chen, L.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280. (n) Huang, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (o) Dureault, A.; Portal, M.; Depezay, J. C. Synlett 1991, 225. (p) Reitz, A. B.; Baxter, E. W. Tetrahedron Lett. 1990, 31, 6777. (q) Shing, T. K. M. Tetrahedron 1988, 44, 7261. (r) Fleet, G. W. J.; Smith, P. W. Tetrahedron 1987, 43, 971. (s) Card, P. J.; Hitz, W. D. J. Org. Chem. 1985, 50, 891.
39. For more recent literatures for the synthesis and biological activity of I, see: (a) Donohoe, T. J.; Headley, C. E.; Cousins, R. P. C.; Cowley, A. Org. Lett. 2003, 7, 999. (b) Dondoni, A.; Giovannini, P. P.; Perrone, D. J. Org. Chem. 2002, 67, 7203. (c) Cubero, I.; Plaza Lopez-Espinosa, M. T.; Robles Diaz, R.; Franco Montalban, F. Carbohydr. Res. 2001, 330, 401. (d) Saotome, C.; Kanie, Y.; Kanie, O.; Wong, C.-H. Bioorg. Med. Chem. 2000, 8, 2249. (e) Colobert, F.; Tito, A.; Khiar, N.; Denni, D.; Medina, M. A.; Martin-Lomas, M.; Ruano, J. G.; Solladie, G. J. Org. Chem. 1998, 63, 8918. (f) Takayama, S.; Martin, R.; Wu, J.; Laslo, K.; Siuzdak, G.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 8146. (g) Huwe, C. M.; Blechert, S. Synthesis 1997, 61. (h) McCort, I.; Dureault, A.; Depezay, J.-C. Tetrahedron Lett. 1996, 37, 7717. (i) Asano, N.; Oseki, K.; Kizu, H.; Matsui, K. J. Med. Chem. 1994, 37, 3701. (j) Zou, W.; Szarek, W. A. Carbohydr. Res. 1993, 242, 311. (k) Masaki, Y.; Oda, H.; Kazuta, K.; Usai, A.; Itoh, A.; Xu, F. Tetrahedron Lett. 1992, 33, 5089. (l) Kajimoto, T.; Chen, L.; Liu, K.-C.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113, 6678. (m) Liu, K.-C.; Kajimoto, T.; Chen, L.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280. (n) Huang, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (o) Dureault, A.; Portal, M.; Depezay, J. C. Synlett 1991, 225. (p) Reitz, A. B.; Baxter, E. W. Tetrahedron Lett. 1990, 31, 6777. (q) Shing, T. K. M. Tetrahedron 1988, 44, 7261. (r) Fleet, G. W. J.; Smith, P. W. Tetrahedron 1987, 43, 971. (s) Card, P. J.; Hitz, W. D. J. Org. Chem. 1985, 50, 891.
40. For more recent literatures for the synthesis and biological activity of I, see: (a) Donohoe, T. J.; Headley, C. E.; Cousins, R. P. C.; Cowley, A. Org. Lett. 2003, 7, 999. (b) Dondoni, A.; Giovannini, P. P.; Perrone, D. J. Org. Chem. 2002, 67, 7203. (c) Cubero, I.; Plaza Lopez-Espinosa, M. T.; Robles Diaz, R.; Franco Montalban, F. Carbohydr. Res. 2001, 330, 401. (d) Saotome, C.; Kanie, Y.; Kanie, O.; Wong, C.-H. Bioorg. Med. Chem. 2000, 8, 2249. (e) Colobert, F.; Tito, A.; Khiar, N.; Denni, D.; Medina, M. A.; Martin-Lomas, M.; Ruano, J. G., Solladie, G. J. Org. Chem. 1998, 63, 8918. (f) Takayama, S.; Martin, R.; Wu, J.; Laslo, K.; Siuzdak, G.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 8146. (g) Huwe, C. M.; Blechert, S. Synthesis 1997, 61. (h) McCort, I.; Dureault, A.; Depezay, J.-C. Tetrahedron Lett. 1996, 37, 7717. (i) Asano, N.; Oseki, K.; Kizu, H.; Matsui, K. J. Med. Chem. 1994, 37, 3701. (j) Zou, W.; Szarek, W. A. Carbohydr. Res. 1993, 242, 311. (k) Masaki, Y.; Oda, H.; Kazuta, K.; Usai, A.; Itoh, A.; Xu, F. Tetrahedron Lett. 1992, 33, 5089. (l) Kajimoto, T.; Chen, L.; Liu, K.-C.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113, 6678. (m) Liu, K.-C.; Kajimoto, T.; Chen, L.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280. (n) Huang, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (o) Dureault, A.; Portal, M.; Depezay, J. C. Synlett 1991, 225. (p) Reitz, A. B.; Baxter, E. W. Tetrahedron Lett. 1990, 31, 6777. (q) Shing, T. K. M. Tetrahedron 1988, 44, 7261. (r) Fleet, G. W. J.; Smith, P. W. Tetrahedron 1987, 43, 971. (s) Card, P. J.; Hitz, W. D. J. Org. Chem. 1985, 50, 891.
41. For more recent literatures for the synthesis and biological activity of I, see: (a) Donohoe, T. J.; Headley, C. E.; Cousins, R. P. C.; Cowley, A. Org. Lett. 2003, 7, 999. (b) Dondoni, A.; Giovannini, P. P.; Perrone, D. J. Org. Chem. 2002, 67, 7203. (c) Cubero, I.; Plaza Lopez-Espinosa, M. T.; Robles Diaz, R.; Franco Montalban, F. Carbohydr. Res. 2001, 330, 401. (d) Saotome, C.; Kanie, Y.; Kanie, O.; Wong, C.-H. Bioorg. Med. Chem. 2000, 8, 2249. (e) Colobert, F.; Tito, A.; Khiar, N.; Denni, D.; Medina, M. A.; Martin-Lomas, M.; Ruano, J. G., Solladie, G. J. Org. Chem. 1998, 63, 8918. (f) Takayama, S.; Martin, R.; Wu, J.; Laslo, K.; Siuzdak, G.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 8146. (g) Huwe, C. M.; Blechert, S. Synthesis 1997, 61. (h) McCort, I.; Dureault, A.; Depezay, J.-C. Tetrahedron Lett. 1996, 37, 7717. (i) Asano, N.; Oseki, K.; Kizu, H.; Matsui, K. J. Med. Chem. 1994, 37, 3701. (j) Zou, W.; Szarek, W. A. Carbohydr. Res. 1993, 242, 311. (k) Masaki, Y.; Oda, H.; Kazuta, K.; Usai, A.; Itoh, A.; Xu, F. Tetrahedron Lett. 1992, 33, 5089. (l) Kajimoto, T.; Chen, L.; Liu, K.-C.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113, 6678. (m) Liu, K.-C.; Kajimoto, T.; Chen, L.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280. (n) Huang, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (o) Dureault, A.; Portal, M.; Depezay, J. C. Synlett 1991, 225. (p) Reitz, A. B.; Baxter, E. W. Tetrahedron Lett. 1990, 31, 6777. (q) Shing, T. K. M. Tetrahedron 1988, 44, 7261. (r) Fleet, G. W. J.; Smith, P. W. Tetrahedron 1987, 43, 971. (s) Card, P. J.; Hitz, W. D. J. Org. Chem. 1985, 50, 891.
42. For more recent literatures for the synthesis and biological activity of I, see: (a) Donohoe, T. J.; Headley, C. E.; Cousins, R. P. C.; Cowley, A. Org. Lett. 2003, 7, 999. (b) Dondoni, A.; Giovannini, P. P.; Perrone, D. J. Org. Chem. 2002, 67, 7203. (c) Cubero, I.; Plaza Lopez-Espinosa, M. T.; Robles Diaz, R.; Franco Montalban, F. Carbohydr. Res. 2001, 330, 401. (d) Saotome, C.; Kanie, Y.; Kanie, O.; Wong, C.-H. Bioorg. Med. Chem. 2000, 8, 2249. (e) Colobert, F.; Tito, A.; Khiar, N.; Denni, D.; Medina, M. A.; Martin-Lomas, M.; Ruano, J. G., Solladie, G. J. Org. Chem. 1998, 63, 8918. (f) Takayama, S.; Martin, R.; Wu, J.; Laslo, K.; Siuzdak, G.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 8146. (g) Huwe, C. M.; Blechert, S. Synthesis 1997, 61. (h) McCort, I.; Dureault, A.; Depezay, J.-C. Tetrahedron Lett. 1996, 37, 7717. (i) Asano, N.; Oseki, K.; Kizu, H.; Matsui, K. J. Med. Chem. 1994, 37, 3701. (j) Zou, W.; Szarek, W. A. Carbohydr. Res. 1993, 242, 311. (k) Masaki, Y.; Oda, H.; Kazuta, K.; Usai, A.; Itoh, A.; Xu, F. Tetrahedron Lett. 1992, 33, 5089. (l) Kajimoto, T.; Chen, L.; Liu, K.-C.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113, 6678. (m) Liu, K.-C.; Kajimoto, T.; Chen, L.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280. (n) Huang, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (o) Dureault, A.; Portal, M.; Depezay, J. C. Synlett 1991, 225. (p) Reitz, A. B.; Baxter, E. W. Tetrahedron Lett. 1990, 31, 6777. (q) Shing, T. K. M. Tetrahedron 1988, 44, 7261. (r) Fleet, G. W. J.; Smith, P. W. Tetrahedron 1987, 43, 971. (s) Card, P. J.; Hitz, W. D. J. Org. Chem. 1985, 50, 891.
43. For more recent literatures for the synthesis and biological activity of I, see: (a) Donohoe, T. J.; Headley, C. E.; Cousins, R. P. C.; Cowley, A. Org. Lett. 2003, 7, 999. (b) Dondoni, A.; Giovannini, P. P.; Perrone, D. J. Org. Chem. 2002, 67, 7203. (c) Cubero, I.; Plaza Lopez-Espinosa, M. T.; Robles Diaz, R.; Franco Montalban, F. Carbohydr. Res. 2001, 330, 401. (d) Saotome, C.; Kanie, Y.; Kanie, O.; Wong, C.-H. Bioorg. Med. Chem. 2000, 8, 2249. (e) Colobert, F.; Tito, A.; Khiar, N.; Denni, D.; Medina, M. A.; Martin-Lomas, M.; Ruano, J. G., Solladie, G. J. Org. Chem. 1998, 63, 8918. (f) Takayama, S.; Martin, R.; Wu, J.; Laslo, K.; Siuzdak, G.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 8146. (g) Huwe, C. M.; Blechert, S. Synthesis 1997, 61. (h) McCort, I.; Dureault, A.; Depezay, J.-C. Tetrahedron Lett. 1996, 37, 7717. (i) Asano, N.; Oseki, K.; Kizu, H.; Matsui, K. J. Med. Chem. 1994, 37, 3701. (j) Zou, W.; Szarek, W. A. Carbohydr. Res. 1993, 242, 311. (k) Masaki, Y.; Oda, H.; Kazuta, K.; Usai, A.; Itoh, A.; Xu, F. Tetrahedron Lett. 1992, 33, 5089. (l) Kajimoto, T.; Chen, L.; Liu, K.-C.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113, 6678. (m) Liu, K.-C.; Kajimoto, T.; Chen, L.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280. (n) Huang, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (o) Dureault, A.; Portal, M.; Depezay, J. C. Synlett 1991, 225. (p) Reitz, A. B.; Baxter, E. W. Tetrahedron Lett. 1990, 31, 6777. (q) Shing, T. K. M. Tetrahedron 1988, 44, 7261. (r) Fleet, G. W. J.; Smith, P. W. Tetrahedron 1987, 43, 971. (s) Card, P. J.; Hitz, W. D. J. Org. Chem. 1985, 50, 891.
44. For more recent literatures for the synthesis and biological activity of I, see: (a) Donohoe, T. J.; Headley, C. E.; Cousins, R. P. C.; Cowley, A. Org. Lett. 2003, 7, 999. (b) Dondoni, A.; Giovannini, P. P.; Perrone, D. J. Org. Chem. 2002, 67, 7203. (c) Cubero, I.; Plaza Lopez-Espinosa, M. T.; Robles Diaz, R.; Franco Montalban, F. Carbohydr. Res. 2001, 330, 401. (d) Saotome, C.; Kanie, Y.; Kanie, O.; Wong, C.-H. Bioorg. Med. Chem. 2000, 8, 2249. (e) Colobert, F.; Tito, A.; Khiar, N.; Denni, D.; Medina, M. A.; Martin-Lomas, M.; Ruano, J. G., Solladie, G. J. Org. Chem. 1998, 63, 8918. (f) Takayama, S.; Martin, R.; Wu, J.; Laslo, K.; Siuzdak, G.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 8146. (g) Huwe, C. M.; Blechert, S. Synthesis 1997, 61. (h) McCort, I.; Dureault, A.; Depezay, J.-C. Tetrahedron Lett. 1996, 37, 7717. (i) Asano, N.; Oseki, K.; Kizu, H.; Matsui, K. J. Med. Chem. 1994, 37, 3701. (j) Zou, W.; Szarek, W. A. Carbohydr. Res. 1993, 242, 311. (k) Masaki, Y.; Oda, H.; Kazuta, K.; Usai, A.; Itoh, A.; Xu, F. Tetrahedron Lett. 1992, 33, 5089. (l) Kajimoto, T.; Chen, L.; Liu, K.-C.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113, 6678. (m) Liu, K.-C.; Kajimoto, T.; Chen, L.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280. (n) Huang, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (o) Dureault, A.; Portal, M.; Depezay, J. C. Synlett 1991, 225. (p) Reitz, A. B.; Baxter, E. W. Tetrahedron Lett. 1990, 31, 6777. (q) Shing, T. K. M. Tetrahedron 1988, 44, 7261. (r) Fleet, G. W. J.; Smith, P. W. Tetrahedron 1987, 43, 971. (s) Card, P. J.; Hitz, W. D. J. Org. Chem. 1985, 50, 891.
45. For more recent literatures for the synthesis and biological activity of I, see: (a) Donohoe, T. J.; Headley, C. E.; Cousins, R. P. C.; Cowley, A. Org. Lett. 2003, 7, 999. (b) Dondoni, A.; Giovannini, P. P.; Perrone, D. J. Org. Chem. 2002, 67, 7203. (c) Cubero, I.; Plaza Lopez-Espinosa, M. T.; Robles Diaz, R.; Franco Montalban, F. Carbohydr. Res. 2001, 330, 401. (d) Saotome, C.; Kanie, Y.; Kanie, O.; Wong, C.-H. Bioorg. Med. Chem. 2000, 8, 2249. (e) Colobert, F.; Tito, A.; Khiar, N.; Denni, D.; Medina, M. A.; Martin-Lomas, M.; Ruano, J. G., Solladie, G. J. Org. Chem. 1998, 63, 8918. (f) Takayama, S.; Martin, R.; Wu, J.; Laslo, K.; Siuzdak, G.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 8146. (g) Huwe, C. M.; Blechert, S. Synthesis 1997, 61. (h) McCort, I.; Dureault, A.; Depezay, J.-C. Tetrahedron Lett. 1996, 37, 7717. (i) Asano, N.; Oseki, K.; Kizu, H.; Matsui, K. J. Med. Chem. 1994, 37, 3701. (j) Zou, W.; Szarek, W. A. Carbohydr. Res. 1993, 242, 311. (k) Masaki, Y.; Oda, H.; Kazuta, K.; Usai, A.; Itoh, A.; Xu, F. Tetrahedron Lett. 1992, 33, 5089. (l) Kajimoto, T.; Chen, L.; Liu, K.-C.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113, 6678. (m) Liu, K.-C.; Kajimoto, T.; Chen, L.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280. (n) Huang, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (o) Dureault, A.; Portal, M.; Depezay, J. C. Synlett 1991, 225. (p) Reitz, A. B.; Baxter, E. W. Tetrahedron Lett. 1990, 31, 6777. (q) Shing, T. K. M. Tetrahedron 1988, 44, 7261. (r) Fleet, G. W. J.; Smith, P. W. Tetrahedron 1987, 43, 971. (s) Card, P. J.; Hitz, W. D. J. Org. Chem. 1985, 50, 891.
46. For more recent literatures for the synthesis and biological activity of I, see: (a) Donohoe, T. J.; Headley, C. E.; Cousins, R. P. C.; Cowley, A. Org. Lett. 2003, 7, 999. (b) Dondoni, A.; Giovannini, P. P.; Perrone, D. J. Org. Chem. 2002, 67, 7203. (c) Cubero, I.; Plaza Lopez-Espinosa, M. T.; Robles Diaz, R.; Franco Montalban, F. Carbohydr. Res. 2001, 330, 401. (d) Saotome, C.; Kanie, Y.; Kanie, O.; Wong, C.-H. Bioorg. Med. Chem. 2000, 8, 2249. (e) Colobert, F.; Tito, A.; Khiar, N.; Denni, D.; Medina, M. A.; Martin-Lomas, M.; Ruano, J. G., Solladie, G. J. Org. Chem. 1998, 63, 8918. (f) Takayama, S.; Martin, R.; Wu, J.; Laslo, K.; Siuzdak, G.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 8146. (g) Huwe, C. M.; Blechert, S. Synthesis 1997, 61. (h) McCort, I.; Dureault, A.; Depezay, J.-C. Tetrahedron Lett. 1996, 37, 7717. (i) Asano, N.; Oseki, K.; Kizu, H.; Matsui, K. J. Med. Chem. 1994, 37, 3701. (j) Zou, W.; Szarek, W. A. Carbohydr. Res. 1993, 242, 311. (k) Masaki, Y.; Oda, H.; Kazuta, K.; Usai, A.; Itoh, A.; Xu, F. Tetrahedron Lett. 1992, 33, 5089. (l) Kajimoto, T.; Chen, L.; Liu, K.-C.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113, 6678. (m) Liu, K.-C.; Kajimoto, T.; Chen, L.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280. (n) Huang, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (o) Dureault, A.; Portal, M.; Depezay, J. C. Synlett 1991, 225. (p) Reitz, A. B.; Baxter, E. W. Tetrahedron Lett. 1990, 31, 6777. (q) Shing, T. K. M. Tetrahedron 1988, 44, 7261. (r) Fleet, G. W. J.; Smith, P. W. Tetrahedron 1987, 43, 971. (s) Card, P. J.; Hitz, W. D. J. Org. Chem. 1985, 50, 891.
47. For more recent literatures for the synthesis and biological activity of I, see: (a) Donohoe, T. J.; Headley, C. E.; Cousins, R. P. C.; Cowley, A. Org. Lett. 2003, 7, 999. (b) Dondoni, A.; Giovannini, P. P.; Perrone, D. J. Org. Chem. 2002, 67, 7203. (c) Cubero, I.; Plaza Lopez-Espinosa, M. T.; Robles Diaz, R.; Franco Montalban, F. Carbohydr. Res. 2001, 330, 401. (d) Saotome, C.; Kanie, Y.; Kanie, O.; Wong, C.-H. Bioorg. Med. Chem. 2000, 8, 2249. (e) Colobert, F.; Tito, A.; Khiar, N.; Denni, D.; Medina, M. A.; Martin-Lomas, M.; Ruano, J. G., Solladie, G. J. Org. Chem. 1998, 63, 8918. (f) Takayama, S.; Martin, R.; Wu, J.; Laslo, K.; Siuzdak, G.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 8146. (g) Huwe, C. M.; Blechert, S. Synthesis 1997, 61. (h) McCort, I.; Dureault, A.; Depezay, J.-C. Tetrahedron Lett. 1996, 37, 7717. (i) Asano, N.; Oseki, K.; Kizu, H.; Matsui, K. J. Med. Chem. 1994, 37, 3701. (j) Zou, W.; Szarek, W. A. Carbohydr. Res. 1993, 242, 311. (k) Masaki, Y.; Oda, H.; Kazuta, K.; Usai, A.; Itoh, A.; Xu, F. Tetrahedron Lett. 1992, 33, 5089. (l) Kajimoto, T.; Chen, L.; Liu, K.-C.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113, 6678. (m) Liu, K.-C.; Kajimoto, T.; Chen, L.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280. (n) Huang, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (o) Dureault, A.; Portal, M.; Depezay, J. C. Synlett 1991, 225. (p) Reitz, A. B.; Baxter, E. W. Tetrahedron Lett. 1990, 31, 6777. (q) Shing, T. K. M. Tetrahedron 1988, 44, 7261. (r) Fleet, G. W. J.; Smith, P. W. Tetrahedron 1987, 43, 971. (s) Card, P. J.; Hitz, W. D. J. Org. Chem. 1985, 50, 891.
48. For more recent literatures for the synthesis and biological activity of I, see: (a) Donohoe, T. J.; Headley, C. E.; Cousins, R. P. C.; Cowley, A. Org. Lett. 2003, 7, 999. (b) Dondoni, A.; Giovannini, P. P.; Perrone, D. J. Org. Chem. 2002, 67, 7203. (c) Cubero, I.; Plaza Lopez-Espinosa, M. T.; Robles Diaz, R.; Franco Montalban, F. Carbohydr. Res. 2001, 330, 401. (d) Saotome, C.; Kanie, Y.; Kanie, O.; Wong, C.-H. Bioorg. Med. Chem. 2000, 8, 2249. (e) Colobert, F.; Tito, A.; Khiar, N.; Denni, D.; Medina, M. A.; Martin-Lomas, M.; Ruano, J. G., Solladie, G. J. Org. Chem. 1998, 63, 8918. (f) Takayama, S.; Martin, R.; Wu, J.; Laslo, K.; Siuzdak, G.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 8146. (g) Huwe, C. M.; Blechert, S. Synthesis 1997, 61. (h) McCort, I.; Dureault, A.; Depezay, J.-C. Tetrahedron Lett. 1996, 37, 7717. (i) Asano, N.; Oseki, K.; Kizu, H.; Matsui, K. J. Med. Chem. 1994, 37, 3701. (j) Zou, W.; Szarek, W. A. Carbohydr. Res. 1993, 242, 311. (k) Masaki, Y.; Oda, H.; Kazuta, K.; Usai, A.; Itoh, A.; Xu, F. Tetrahedron Lett. 1992, 33, 5089. (l) Kajimoto, T.; Chen, L.; Liu, K.-C.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113, 6678. (m) Liu, K.-C.; Kajimoto, T.; Chen, L.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280. (n) Huang, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (o) Dureault, A.; Portal, M.; Depezay, J. C. Synlett 1991, 225. (p) Reitz, A. B.; Baxter, E. W. Tetrahedron Lett. 1990, 31, 6777. (q) Shing, T. K. M. Tetrahedron 1988, 44, 7261. (r) Fleet, G. W. J.; Smith, P. W. Tetrahedron 1987, 43, 971. (s) Card, P. J.; Hitz, W. D. J. Org. Chem. 1985, 50, 891.
49. For more recent literatures for the synthesis and biological activity of I, see: (a) Donohoe, T. J.; Headley, C. E.; Cousins, R. P. C.; Cowley, A. Org. Lett. 2003, 7, 999. (b) Dondoni, A.; Giovannini, P. P.; Perrone, D. J. Org. Chem. 2002, 67, 7203. (c) Cubero, I.; Plaza Lopez-Espinosa, M. T.; Robles Diaz, R.; Franco Montalban, F. Carbohydr. Res. 2001, 330, 401. (d) Saotome, C.; Kanie, Y.; Kanie, O.; Wong, C.-H. Bioorg. Med. Chem. 2000, 8, 2249. (e) Colobert, F.; Tito, A.; Khiar, N.; Denni, D.; Medina, M. A.; Martin-Lomas, M.; Ruano, J. G., Solladie, G. J. Org. Chem. 1998, 63, 8918. (f) Takayama, S.; Martin, R.; Wu, J.; Laslo, K.; Siuzdak, G.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 8146. (g) Huwe, C. M.; Blechert, S. Synthesis 1997, 61. (h) McCort, I.; Dureault, A.; Depezay, J.-C. Tetrahedron Lett. 1996, 37, 7717. (i) Asano, N.; Oseki, K.; Kizu, H.; Matsui, K. J. Med. Chem. 1994, 37, 3701. (j) Zou, W.; Szarek, W. A. Carbohydr. Res. 1993, 242, 311. (k) Masaki, Y.; Oda, H.; Kazuta, K.; Usai, A.; Itoh, A.; Xu, F. Tetrahedron Lett. 1992, 33, 5089. (l) Kajimoto, T.; Chen, L.; Liu, K.-C.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113, 6678. (m) Liu, K.-C.; Kajimoto, T.; Chen, L.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280. (n) Huang, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (o) Dureault, A.; Portal, M.; Depezay, J. C. Synlett 1991, 225. (p) Reitz, A. B.; Baxter, E. W. Tetrahedron Lett. 1990, 31, 6777. (q) Shing, T. K. M. Tetrahedron 1988, 44, 7261. (r) Fleet, G. W. J.; Smith, P. W. Tetrahedron 1987, 43, 971. (s) Card, P. J.; Hitz, W. D. J. Org. Chem. 1985, 50, 891.
50. For more recent literatures for the synthesis and biological activity of I, see: (a) Donohoe, T. J.; Headley, C. E.; Cousins, R. P. C.; Cowley, A. Org. Lett. 2003, 7, 999. (b) Dondoni, A.; Giovannini, P. P.; Perrone, D. J. Org. Chem. 2002, 67, 7203. (c) Cubero, I.; Plaza Lopez-Espinosa, M. T.; Robles Diaz, R.; Franco Montalban, F. Carbohydr. Res. 2001, 330, 401. (d) Saotome, C.; Kanie, Y.; Kanie, O.; Wong, C.-H. Bioorg. Med. Chem. 2000, 8, 2249. (e) Colobert, F.; Tito, A.; Khiar, N.; Denni, D.; Medina, M. A.; Martin-Lomas, M.; Ruano, J. G., Solladie, G. J. Org. Chem. 1998, 63, 8918. (f) Takayama, S.; Martin, R.; Wu, J.; Laslo, K.; Siuzdak, G.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 8146. (g) Huwe, C. M.; Blechert, S. Synthesis 1997, 61. (h) McCort, I.; Dureault, A.; Depezay, J.-C. Tetrahedron Lett. 1996, 37, 7717. (i) Asano, N.; Oseki, K.; Kizu, H.; Matsui, K. J. Med. Chem. 1994, 37, 3701. (j) Zou, W.; Szarek, W. A. Carbohydr. Res. 1993, 242, 311. (k) Masaki, Y.; Oda, H.; Kazuta, K.; Usai, A.; Itoh, A.; Xu, F. Tetrahedron Lett. 1992, 33, 5089. (l) Kajimoto, T.; Chen, L.; Liu, K.-C.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113, 6678. (m) Liu, K.-C.; Kajimoto, T.; Chen, L.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280. (n) Huang, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (o) Dureault, A.; Portal, M.; Depezay, J. C. Synlett 1991, 225. (p) Reitz, A. B.; Baxter, E. W. Tetrahedron Lett. 1990, 31, 6777. (q) Shing, T. K. M. Tetrahedron 1988, 44, 7261. (r) Fleet, G. W. J.; Smith, P. W. Tetrahedron 1987, 43, 971. (s) Card, P. J.; Hitz, W. D. J. Org. Chem. 1985, 50, 891.
51. For more recent literatures for the synthesis and biological activity of I, see: (a) Donohoe, T. J.; Headley, C. E.; Cousins, R. P. C.; Cowley, A. Org. Lett. 2003, 7, 999. (b) Dondoni, A.; Giovannini, P. P.; Perrone, D. J. Org. Chem. 2002, 67, 7203. (c) Cubero, I.; Plaza Lopez-Espinosa, M. T.; Robles Diaz, R.; Franco Montalban, F. Carbohydr. Res. 2001, 330, 401. (d) Saotome, C.; Kanie, Y.; Kanie, O.; Wong, C.-H. Bioorg. Med. Chem. 2000, 8, 2249. (e) Colobert, F.; Tito, A.; Khiar, N.; Denni, D.; Medina, M. A.; Martin-Lomas, M.; Ruano, J. G., Solladie, G. J. Org. Chem. 1998, 63, 8918. (f) Takayama, S.; Martin, R.; Wu, J.; Laslo, K.; Siuzdak, G.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 8146. (g) Huwe, C. M.; Blechert, S. Synthesis 1997, 61. (h) McCort, I.; Dureault, A.; Depezay, J.-C. Tetrahedron Lett. 1996, 37, 7717. (i) Asano, N.; Oseki, K.; Kizu, H.; Matsui, K. J. Med. Chem. 1994, 37, 3701. (j) Zou, W.; Szarek, W. A. Carbohydr. Res. 1993, 242, 311. (k) Masaki, Y.; Oda, H.; Kazuta, K.; Usai, A.; Itoh, A.; Xu, F. Tetrahedron Lett. 1992, 33, 5089. (l) Kajimoto, T.; Chen, L.; Liu, K.-C.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113, 6678. (m) Liu, K.-C.; Kajimoto, T.; Chen, L.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280. (n) Huang, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (o) Dureault, A.; Portal, M.; Depezay, J. C. Synlett 1991, 225. (p) Reitz, A. B.; Baxter, E. W. Tetrahedron Lett. 1990, 31, 6777. (q) Shing, T. K. M. Tetrahedron 1988, 44, 7261. (r) Fleet, G. W. J.; Smith, P. W. Tetrahedron 1987, 43, 971. (s) Card, P. J.; Hitz, W. D. J. Org. Chem. 1985, 50, 891.
52. For more recent literatures for the synthesis and biological activity of I, see: (a) Donohoe, T. J.; Headley, C. E.; Cousins, R. P. C.; Cowley, A. Org. Lett. 2003, 7, 999. (b) Dondoni, A.; Giovannini, P. P.; Perrone, D. J. Org. Chem. 2002, 67, 7203. (c) Cubero, I.; Plaza Lopez-Espinosa, M. T.; Robles Diaz, R.; Franco Montalban, F. Carbohydr. Res. 2001, 330, 401. (d) Saotome, C.; Kanie, Y.; Kanie, O.; Wong, C.-H. Bioorg. Med. Chem. 2000, 8, 2249. (e) Colobert, F.; Tito, A.; Khiar, N.; Denni, D.; Medina, M. A.; Martin-Lomas, M.; Ruano, J. G., Solladie, G. J. Org. Chem. 1998, 63, 8918. (f) Takayama, S.; Martin, R.; Wu, J.; Laslo, K.; Siuzdak, G.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 8146. (g) Huwe, C. M.; Blechert, S. Synthesis 1997, 61. (h) McCort, I.; Dureault, A.; Depezay, J.-C. Tetrahedron Lett. 1996, 37, 7717. (i) Asano, N.; Oseki, K.; Kizu, H.; Matsui, K. J. Med. Chem. 1994, 37, 3701. (j) Zou, W.; Szarek, W. A. Carbohydr. Res. 1993, 242, 311. (k) Masaki, Y.; Oda, H.; Kazuta, K.; Usai, A.; Itoh, A.; Xu, F. Tetrahedron Lett. 1992, 33, 5089. (l) Kajimoto, T.; Chen, L.; Liu, K.-C.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113, 6678. (m) Liu, K.-C.; Kajimoto, T.; Chen, L.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280. (n) Huang, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (o) Dureault, A.; Portal, M.; Depezay, J. C. Synlett 1991, 225. (p) Reitz, A. B.; Baxter, E. W. Tetrahedron Lett. 1990, 31, 6777. (q) Shing, T. K. M. Tetrahedron 1988, 44, 7261. (r) Fleet, G. W. J.; Smith, P. W. Tetrahedron 1987, 43, 971. (s) Card, P. J.; Hitz, W. D. J. Org. Chem. 1985, 50, 891.
53. For more recent literatures for the synthesis and biological activity of I, see: (a) Donohoe, T. J.; Headley, C. E.; Cousins, R. P. C.; Cowley, A. Org. Lett. 2003, 7, 999. (b) Dondoni, A.; Giovannini, P. P.; Perrone, D. J. Org. Chem. 2002, 67, 7203. (c) Cubero, I.; Plaza Lopez-Espinosa, M. T.; Robles Diaz, R.; Franco Montalban, F. Carbohydr. Res. 2001, 330, 401. (d) Saotome, C.; Kanie, Y.; Kanie, O.; Wong, C.-H. Bioorg. Med. Chem. 2000, 8, 2249. (e) Colobert, F.; Tito, A.; Khiar, N.; Denni, D.; Medina, M. A.; Martin-Lomas, M.; Ruano, J. G., Solladie, G. J. Org. Chem. 1998, 63, 8918. (f) Takayama, S.; Martin, R.; Wu, J.; Laslo, K.; Siuzdak, G.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 8146. (g) Huwe, C. M.; Blechert, S. Synthesis 1997, 61. (h) McCort, I.; Dureault, A.; Depezay, J.-C. Tetrahedron Lett. 1996, 37, 7717. (i) Asano, N.; Oseki, K.; Kizu, H.; Matsui, K. J. Med. Chem. 1994, 37, 3701. (j) Zou, W.; Szarek, W. A. Carbohydr. Res. 1993, 242, 311. (k) Masaki, Y.; Oda, H.; Kazuta, K.; Usai, A.; Itoh, A.; Xu, F. Tetrahedron Lett. 1992, 33, 5089. (l) Kajimoto, T.; Chen, L.; Liu, K.-C.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113, 6678. (m) Liu, K.-C.; Kajimoto, T.; Chen, L.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280. (n) Huang, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849. (o) Dureault, A.; Portal, M.; Depezay, J. C. Synlett 1991, 225. (p) Reitz, A. B.; Baxter, E. W. Tetrahedron Lett. 1990, 31, 6777. (q) Shing, T. K. M. Tetrahedron 1988, 44, 7261. (r) Fleet, G. W. J.; Smith, P. W. Tetrahedron 1987, 43, 971. (s) Card, P. J.; Hitz, W. D. J. Org. Chem. 1985, 50, 891.
54. For more recent literatures for the synthesis and biological activity of II, see: (a) Sifferlen, T.; Defoin, A.; Streith, J.; Nouen, D. L.; Tarnus, C.; Dosbaa, I.; Foglietti, M.-J. Tetrahedron 2000, 56, 971. (b) Qiao, L.; Murray, B. W.; Shimazaki, M.; Schultz, J.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 7653. (c) Wang, Y.-F.; Dumas, D. P.; Wong, C.-H. Tetrahedron Lett. 1993, 34, 403. (d) Dumas, D. P.; Kajimoto, T.; Liu, K.-C.; Wong, C.-H.; Berlowitz, D. B.; Danishefsky, S. J. Bioorg. Med. Chem. Lett. 1992, 2, 33. (e) Wong, C.-H.; Dumas, D. P.; Ishikawa, Y.; Koseki, K.; Danishefsky, S. J.; Weston, R. W.; Lowe, J. B. J. Am. Chem. Soc. 1992, 114, 7321. (f) Ishikawa, Y.; Lin, Y. C.; Dumas, D. P.; Shen, G.-J.; Garcia-Junceda, E.; Williams, M. A.; Bayer, R.; Ketcham, C.; Walker, L. E.; Paulson, J. C.; Wong, C.-H. J. Am. Chem. Soc. 1992, 114, 9283. (g) Liu, K.-C.; Kajimoto, T.; Cheng, L.; Zhong, Z.; Ichikawa, Y.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280.
55. For more recent literatures for the synthesis and biological activity of II, see: (a) Sifferlen, T.; Defoin, A.; Streith, J.; Nouen, D. L.; Tarnus, C.; Dosbaa, I.; Foglietti, M.-J. Tetrahedron 2000, 56, 971. (b) Qiao, L.; Murray, B. W.; Shimazaki, M.; Schultz, J.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 7653. (c) Wang, Y.-F.; Dumas, D. P.; Wong, C.-H. Tetrahedron Lett. 1993, 34, 403. (d) Dumas, D. P.; Kajimoto, T.; Liu, K.-C.; Wong, C.-H.; Berlowitz, D. B.; Danishefsky, S. J. Bioorg. Med. Chem. Lett. 1992, 2, 33. (e) Wong, C.-H.; Dumas, D. P.; Ishikawa, Y.; Koseki, K.; Danishefsky, S. J.; Weston, R. W.; Lowe, J. B. J. Am. Chem. Soc. 1992, 114, 7321. (f) Ishikawa, Y.; Lin, Y. C.; Dumas, D. P.; Shen, G.-J.; Garcia-Junceda, E.; Williams, M. A.; Bayer, R.; Ketcham, C.; Walker, L. E.; Paulson, J. C.; Wong, C.-H. J. Am. Chem. Soc. 1992, 114, 9283. (g) Liu, K.-C.; Kajimoto, T.; Cheng, L.; Zhong, Z.; Ichikawa, Y.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280.
56. For more recent literatures for the synthesis and biological activity of II, see: (a) Sifferlen, T.; Defoin, A.; Streith, J.; Nouen, D. L.; Tarnus, C.; Dosbaa, I.; Foglietti, M.-J. Tetrahedron 2000, 56, 971. (b) Qiao, L.; Murray, B. W.; Shimazaki, M.; Schultz, J.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 7653. (c) Wang, Y.-F.; Dumas, D. P.; Wong, C.-H. Tetrahedron Lett. 1993, 34, 403. (d) Dumas, D. P.; Kajimoto, T.; Liu, K.-C.; Wong, C.-H.; Berlowitz, D. B.; Danishefsky, S. J. Bioorg. Med. Chem. Lett. 1992, 2, 33. (e) Wong, C.-H.; Dumas, D. P.; Ishikawa, Y.; Koseki, K.; Danishefsky, S. J.; Weston, R. W.; Lowe, J. B. J. Am. Chem. Soc. 1992, 114, 7321. (f) Ishikawa, Y.; Lin, Y. C.; Dumas, D. P.; Shen, G.-J.; Garcia-Junceda, E.; Williams, M. A.; Bayer, R.; Ketcham, C.; Walker, L. E.; Paulson, J. C.; Wong, C.-H. J. Am. Chem. Soc. 1992, 114, 9283. (g) Liu, K.-C.; Kajimoto, T.; Cheng, L.; Zhong, Z.; Ichikawa, Y.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280.
57. For more recent literatures for the synthesis and biological activity of II, see: (a) Sifferlen, T.; Defoin, A.; Streith, J.; Nouen, D. L.; Tarnus, C.; Dosbaa, I.; Foglietti, M.-J. Tetrahedron 2000, 56, 971. (b) Qiao, L.; Murray, B. W.; Shimazaki, M.; Schultz, J.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 7653. (c) Wang, Y.-F.; Dumas, D. P.; Wong, C.-H. Tetrahedron Lett. 1993, 34, 403. (d) Dumas, D. P.; Kajimoto, T.; Liu, K.-C.; Wong, C.-H.; Berlowitz, D. B.; Danishefsky, S. J. Bioorg. Med. Chem. Lett. 1992, 2, 33. (e) Wong, C.-H.; Dumas, D. P.; Ishikawa, Y.; Koseki, K.; Danishefsky, S. J.; Weston, R. W.; Lowe, J. B. J. Am. Chem. Soc. 1992, 114, 7321. (f) Ishikawa, Y.; Lin, Y. C.; Dumas, D. P.; Shen, G.-J.; Garcia-Junceda, E.; Williams, M. A.; Bayer, R.; Ketcham, C.; Walker, L. E.; Paulson, J. C.; Wong, C.-H. J. Am. Chem. Soc. 1992, 114, 9283. (g) Liu, K.-C.; Kajimoto, T.; Cheng, L.; Zhong, Z.; Ichikawa, Y.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280.
58. For more recent literatures for the synthesis and biological activity of II, see: (a) Sifferlen, T.; Defoin, A.; Streith, J.; Nouen, D. L.; Tarnus, C.; Dosbaa, I.; Foglietti, M.-J. Tetrahedron 2000, 56, 971. (b) Qiao, L.; Murray, B. W.; Shimazaki, M.; Schultz, J.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 7653. (c) Wang, Y.-F.; Dumas, D. P.; Wong, C.-H. Tetrahedron Lett. 1993, 34, 403. (d) Dumas, D. P.; Kajimoto, T.; Liu, K.-C.; Wong, C.-H.; Berlowitz, D. B.; Danishefsky, S. J. Bioorg. Med. Chem. Lett. 1992, 2, 33. (e) Wong, C.-H.; Dumas, D. P.; Ishikawa, Y.; Koseki, K.; Danishefsky, S. J.; Weston, R. W.; Lowe, J. B. J. Am. Chem. Soc. 1992, 114, 7321. (f) Ishikawa, Y.; Lin, Y. C.; Dumas, D. P.; Shen, G.-J.; Garcia-Junceda, E.; Williams, M. A.; Bayer, R.; Ketcham, C.; Walker, L. E.; Paulson, J. C.; Wong, C.-H. J. Am. Chem. Soc. 1992, 114, 9283. (g) Liu, K.-C.; Kajimoto, T.; Cheng, L.; Zhong, Z.; Ichikawa, Y.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280.
59. For more recent literatures for the synthesis and biological activity of II, see: (a) Sifferlen, T.; Defoin, A.; Streith, J.; Nouen, D. L.; Tarnus, C.; Dosbaa, I.; Foglietti, M.-J. Tetrahedron 2000, 56, 971. (b) Qiao, L.; Murray, B. W.; Shimazaki, M.; Schultz, J.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 7653. (c) Wang, Y.-F.; Dumas, D. P.; Wong, C.-H. Tetrahedron Lett. 1993, 34, 403. (d) Dumas, D. P.; Kajimoto, T.; Liu, K.-C.; Wong, C.-H.; Berlowitz, D. B.; Danishefsky, S. J. Bioorg. Med. Chem. Lett. 1992, 2, 33. (e) Wong, C.-H.; Dumas, D. P.; Ishikawa, Y.; Koseki, K.; Danishefsky, S. J.; Weston, R. W.; Lowe, J. B. J. Am. Chem. Soc. 1992, 114, 7321. (f) Ishikawa, Y.; Lin, Y. C.; Dumas, D. P.; Shen, G.-J.; Garcia-Junceda, E.; Williams, M. A.; Bayer, R.; Ketcham, C.; Walker, L. E.; Paulson, J. C.; Wong, C.-H. J. Am. Chem. Soc. 1992, 114, 9283. (g) Liu, K.-C.; Kajimoto, T.; Cheng, L.; Zhong, Z.; Ichikawa, Y.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280.
60. For more recent literatures for the synthesis and biological activity of II, see: (a) Sifferlen, T.; Defoin, A.; Streith, J.; Nouen, D. L.; Tarnus, C.; Dosbaa, I.; Foglietti, M.-J. Tetrahedron 2000, 56, 971. (b) Qiao, L.; Murray, B. W.; Shimazaki, M.; Schultz, J.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 7653. (c) Wang, Y.-F.; Dumas, D. P.; Wong, C.-H. Tetrahedron Lett. 1993, 34, 403. (d) Dumas, D. P.; Kajimoto, T.; Liu, K.-C.; Wong, C.-H.; Berlowitz, D. B.; Danishefsky, S. J. Bioorg. Med. Chem. Lett. 1992, 2, 33. (e) Wong, C.-H.; Dumas, D. P.; Ishikawa, Y.; Koseki, K.; Danishefsky, S. J.; Weston, R. W.; Lowe, J. B. J. Am. Chem. Soc. 1992, 114, 7321. (f) Ishikawa, Y.; Lin, Y. C.; Dumas, D. P.; Shen, G.-J.; Garcia-Junceda, E.; Williams, M. A.; Bayer, R.; Ketcham, C.; Walker, L. E.; Paulson, J. C.; Wong, C.-H. J. Am. Chem. Soc. 1992, 114, 9283. (g) Liu, K.-C.; Kajimoto, T.; Cheng, L.; Zhong, Z.; Ichikawa, Y.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280.
61. (a) Han, H.; Cho, C. W.; Janda, K. D. Chem. Eur. J. 1999, 5, 1565.
62. (b) Han, H.; Yoon, J.; Janda, K. D. J. Org. Chem. 1998, 63, 2045.
63. (c) Singh, O. V.; Han, H. Tetrahedron Lett. 2003, 44, 2387.
64. (d) Han, H.; Yang, H. Tetrahedron Lett. 2003, 44, 1567.
65. (e) For other similar approaches, see: Morgan, A. J.; Masse, C. E.; Panek, J. S. Org. Lett. 1999, 1, 1949.
66. (f) Also see: Chuang, C.-C.; Vassar, V.; Ma, Z.; Geney, R.; Ojima, I. Chirality 2002, 14, 151.
67. (a) Takahata, H.; Takehara, H.; Ohkubo, N.; Takefumi, M. Tetrahedron: Asymmetry 1990, 1, 561.
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73. 2O) δ 1.27 (d, 3 H, J = 7.0 Hz), 3.75 (dd, 1 H, J = 7.5 Hz, 10.5 Hz), 3.77-3.87 (m, 3 H), 4.06 (d, 1 H, J = 3.5 Hz), 4.26 (d, 1 H, J = 3.5Hz).