Polyhydroxy amino acid derivatives via β-lactams using enantiospecific approaches and microwave techniques

Tetrahedron

Volumn 56, Issue 31, 2000, Pages 5603-5619

  Bose, Ajay K ^b   Banik, B K ^c   Mathur, Chandra ^c   Wagle, Dilip R ^c   Manhas, Maghar S ^c  

^a UNIVERSITY OF TEXAS   (United States)

^b Stevens Institute of Technology   (United States)

^c NONE

Author keywords

Amino acids; Amino sugars; Annulation; Azetidinones; Enantiospecific; Microwave irradiation

Indexed keywords

AMINO ACID DERIVATIVE; BETA LACTAM ANTIBIOTIC; HYDROXYAMINO ACID;

CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFERENCE PAPER; DRUG SYNTHESIS; ENANTIOMER; MICROWAVE RADIATION; PRIORITY JOURNAL; STEREOSPECIFICITY; STRUCTURE ANALYSIS;

EID: 0034725843     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00410-5     Document Type: Article

References (87)

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62. For the use of ammonium formate in catalytic transfer hydrogenation method, see: (a) Anwar, M. K.; Spatola, A. F. Synthesis 1980, 929. (b) Carpino, L.; Tunga, A. J. Org. Chem. 1986, 51, 1930. (c) Overman, L. E.; Sugai, S. Helv. Chim. Acta 1985, 68, 745. (d) Ram, S.; Ehrenkaufer, R. E. Synthesis 1988, 91.
63. For the use of ammonium formate in catalytic transfer hydrogenation method, see: (a) Anwar, M. K.; Spatola, A. F. Synthesis 1980, 929. (b) Carpino, L.; Tunga, A. J. Org. Chem. 1986, 51, 1930. (c) Overman, L. E.; Sugai, S. Helv. Chim. Acta 1985, 68, 745. (d) Ram, S.; Ehrenkaufer, R. E. Synthesis 1988, 91.
64. Isono K., Asahi K., Suzuki S. J. Am. Chem. Soc. 91:1969;7499.
65. For the synthesis of natural and unnatural polyoxamic acid, see: (a) Kuzuhara, H.; Emoto, S. Tetrahedron Lett. 1973, 5051. (b) Kuzuhara, H.; Kimura, M.; Emoto, S. Carbohydr. Res. 1975, 45, 245. (c) Saksena, A. K.; Lovey, R. G.; Girijavallabhan, V. M.; Ganguly, A. K. J. Org. Chem. 1986, 51, 5024. (d) Hirama, H.; Hioku, H.; Ito, S. Tetrahedron Lett. 1988, 29, 3125. (e) Garner, P.; Park, J. M. J. Org. Chem. 1988, 53, 2979. (f) Savage, I.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1989, 717. (g) Dureault, A.; Carreaux, F.; Depezay, J. C. Synthesis 1990, 46, 265. (h) Paz, M. M.; Sardina, F. J. J. Org. Chem. 1993, 58, 6990. (i) Dondini, A.; Franco, S.; Merchan, F. L.; Merino, P.; Tejero, T. Tetrahedron Lett. 1993, 34, 5479. (j) Matsura, F.; Hamada, Y.; Shioroi, T. Tetrahedron Lett. 1994, 35, 733. (k) Marshall, J. A.; Seletsky, B. M.; Coan, P. S. J. Org. Chem. 1994, 59, 5139. (l) Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. Org. Chem. 1995, 60, 6431. (m) Kang, S. H.; Choi, H. W. Chem Commun. 1996, 1521. (n) Trost, B. M.; Krueger, A. C.; Bunt, R. C., Zombrano, J. J. Am. Chem. Soc. 1996, 118, 6520. (o) Bandini, E.; Martelli, G.; Spunta, G.; Borgini, A.; Panuzio, M.; Piersanti, G. Tetrahedron: Asymmetry 1997, 8, 3717. (p) Veeresa, G.; Dutta, A. Tetrahedron Lett. 1998, 39, 119.
66. For the synthesis of natural and unnatural polyoxamic acid, see: (a) Kuzuhara, H.; Emoto, S. Tetrahedron Lett. 1973, 5051. (b) Kuzuhara, H.; Kimura, M.; Emoto, S. Carbohydr. Res. 1975, 45, 245. (c) Saksena, A. K.; Lovey, R. G.; Girijavallabhan, V. M.; Ganguly, A. K. J. Org. Chem. 1986, 51, 5024. (d) Hirama, H.; Hioku, H.; Ito, S. Tetrahedron Lett. 1988, 29, 3125. (e) Garner, P.; Park, J. M. J. Org. Chem. 1988, 53, 2979. (f) Savage, I.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1989, 717. (g) Dureault, A.; Carreaux, F.; Depezay, J. C. Synthesis 1990, 46, 265. (h) Paz, M. M.; Sardina, F. J. J. Org. Chem. 1993, 58, 6990. (i) Dondini, A.; Franco, S.; Merchan, F. L.; Merino, P.; Tejero, T. Tetrahedron Lett. 1993, 34, 5479. (j) Matsura, F.; Hamada, Y.; Shioroi, T. Tetrahedron Lett. 1994, 35, 733. (k) Marshall, J. A.; Seletsky, B. M.; Coan, P. S. J. Org. Chem. 1994, 59, 5139. (l) Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. Org. Chem. 1995, 60, 6431. (m) Kang, S. H.; Choi, H. W. Chem Commun. 1996, 1521. (n) Trost, B. M.; Krueger, A. C.; Bunt, R. C., Zombrano, J. J. Am. Chem. Soc. 1996, 118, 6520. (o) Bandini, E.; Martelli, G.; Spunta, G.; Borgini, A.; Panuzio, M.; Piersanti, G. Tetrahedron: Asymmetry 1997, 8, 3717. (p) Veeresa, G.; Dutta, A. Tetrahedron Lett. 1998, 39, 119.
67. For the synthesis of natural and unnatural polyoxamic acid, see: (a) Kuzuhara, H.; Emoto, S. Tetrahedron Lett. 1973, 5051. (b) Kuzuhara, H.; Kimura, M.; Emoto, S. Carbohydr. Res. 1975, 45, 245. (c) Saksena, A. K.; Lovey, R. G.; Girijavallabhan, V. M.; Ganguly, A. K. J. Org. Chem. 1986, 51, 5024. (d) Hirama, H.; Hioku, H.; Ito, S. Tetrahedron Lett. 1988, 29, 3125. (e) Garner, P.; Park, J. M. J. Org. Chem. 1988, 53, 2979. (f) Savage, I.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1989, 717. (g) Dureault, A.; Carreaux, F.; Depezay, J. C. Synthesis 1990, 46, 265. (h) Paz, M. M.; Sardina, F. J. J. Org. Chem. 1993, 58, 6990. (i) Dondini, A.; Franco, S.; Merchan, F. L.; Merino, P.; Tejero, T. Tetrahedron Lett. 1993, 34, 5479. (j) Matsura, F.; Hamada, Y.; Shioroi, T. Tetrahedron Lett. 1994, 35, 733. (k) Marshall, J. A.; Seletsky, B. M.; Coan, P. S. J. Org. Chem. 1994, 59, 5139. (l) Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. Org. Chem. 1995, 60, 6431. (m) Kang, S. H.; Choi, H. W. Chem Commun. 1996, 1521. (n) Trost, B. M.; Krueger, A. C.; Bunt, R. C., Zombrano, J. J. Am. Chem. Soc. 1996, 118, 6520. (o) Bandini, E.; Martelli, G.; Spunta, G.; Borgini, A.; Panuzio, M.; Piersanti, G. Tetrahedron: Asymmetry 1997, 8, 3717. (p) Veeresa, G.; Dutta, A. Tetrahedron Lett. 1998, 39, 119.
68. For the synthesis of natural and unnatural polyoxamic acid, see: (a) Kuzuhara, H.; Emoto, S. Tetrahedron Lett. 1973, 5051. (b) Kuzuhara, H.; Kimura, M.; Emoto, S. Carbohydr. Res. 1975, 45, 245. (c) Saksena, A. K.; Lovey, R. G.; Girijavallabhan, V. M.; Ganguly, A. K. J. Org. Chem. 1986, 51, 5024. (d) Hirama, H.; Hioku, H.; Ito, S. Tetrahedron Lett. 1988, 29, 3125. (e) Garner, P.; Park, J. M. J. Org. Chem. 1988, 53, 2979. (f) Savage, I.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1989, 717. (g) Dureault, A.; Carreaux, F.; Depezay, J. C. Synthesis 1990, 46, 265. (h) Paz, M. M.; Sardina, F. J. J. Org. Chem. 1993, 58, 6990. (i) Dondini, A.; Franco, S.; Merchan, F. L.; Merino, P.; Tejero, T. Tetrahedron Lett. 1993, 34, 5479. (j) Matsura, F.; Hamada, Y.; Shioroi, T. Tetrahedron Lett. 1994, 35, 733. (k) Marshall, J. A.; Seletsky, B. M.; Coan, P. S. J. Org. Chem. 1994, 59, 5139. (l) Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. Org. Chem. 1995, 60, 6431. (m) Kang, S. H.; Choi, H. W. Chem Commun. 1996, 1521. (n) Trost, B. M.; Krueger, A. C.; Bunt, R. C., Zombrano, J. J. Am. Chem. Soc. 1996, 118, 6520. (o) Bandini, E.; Martelli, G.; Spunta, G.; Borgini, A.; Panuzio, M.; Piersanti, G. Tetrahedron: Asymmetry 1997, 8, 3717. (p) Veeresa, G.; Dutta, A. Tetrahedron Lett. 1998, 39, 119.
69. For the synthesis of natural and unnatural polyoxamic acid, see: (a) Kuzuhara, H.; Emoto, S. Tetrahedron Lett. 1973, 5051. (b) Kuzuhara, H.; Kimura, M.; Emoto, S. Carbohydr. Res. 1975, 45, 245. (c) Saksena, A. K.; Lovey, R. G.; Girijavallabhan, V. M.; Ganguly, A. K. J. Org. Chem. 1986, 51, 5024. (d) Hirama, H.; Hioku, H.; Ito, S. Tetrahedron Lett. 1988, 29, 3125. (e) Garner, P.; Park, J. M. J. Org. Chem. 1988, 53, 2979. (f) Savage, I.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1989, 717. (g) Dureault, A.; Carreaux, F.; Depezay, J. C. Synthesis 1990, 46, 265. (h) Paz, M. M.; Sardina, F. J. J. Org. Chem. 1993, 58, 6990. (i) Dondini, A.; Franco, S.; Merchan, F. L.; Merino, P.; Tejero, T. Tetrahedron Lett. 1993, 34, 5479. (j) Matsura, F.; Hamada, Y.; Shioroi, T. Tetrahedron Lett. 1994, 35, 733. (k) Marshall, J. A.; Seletsky, B. M.; Coan, P. S. J. Org. Chem. 1994, 59, 5139. (l) Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. Org. Chem. 1995, 60, 6431. (m) Kang, S. H.; Choi, H. W. Chem Commun. 1996, 1521. (n) Trost, B. M.; Krueger, A. C.; Bunt, R. C., Zombrano, J. J. Am. Chem. Soc. 1996, 118, 6520. (o) Bandini, E.; Martelli, G.; Spunta, G.; Borgini, A.; Panuzio, M.; Piersanti, G. Tetrahedron: Asymmetry 1997, 8, 3717. (p) Veeresa, G.; Dutta, A. Tetrahedron Lett. 1998, 39, 119.
70. For the synthesis of natural and unnatural polyoxamic acid, see: (a) Kuzuhara, H.; Emoto, S. Tetrahedron Lett. 1973, 5051. (b) Kuzuhara, H.; Kimura, M.; Emoto, S. Carbohydr. Res. 1975, 45, 245. (c) Saksena, A. K.; Lovey, R. G.; Girijavallabhan, V. M.; Ganguly, A. K. J. Org. Chem. 1986, 51, 5024. (d) Hirama, H.; Hioku, H.; Ito, S. Tetrahedron Lett. 1988, 29, 3125. (e) Garner, P.; Park, J. M. J. Org. Chem. 1988, 53, 2979. (f) Savage, I.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1989, 717. (g) Dureault, A.; Carreaux, F.; Depezay, J. C. Synthesis 1990, 46, 265. (h) Paz, M. M.; Sardina, F. J. J. Org. Chem. 1993, 58, 6990. (i) Dondini, A.; Franco, S.; Merchan, F. L.; Merino, P.; Tejero, T. Tetrahedron Lett. 1993, 34, 5479. (j) Matsura, F.; Hamada, Y.; Shioroi, T. Tetrahedron Lett. 1994, 35, 733. (k) Marshall, J. A.; Seletsky, B. M.; Coan, P. S. J. Org. Chem. 1994, 59, 5139. (l) Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. Org. Chem. 1995, 60, 6431. (m) Kang, S. H.; Choi, H. W. Chem Commun. 1996, 1521. (n) Trost, B. M.; Krueger, A. C.; Bunt, R. C., Zombrano, J. J. Am. Chem. Soc. 1996, 118, 6520. (o) Bandini, E.; Martelli, G.; Spunta, G.; Borgini, A.; Panuzio, M.; Piersanti, G. Tetrahedron: Asymmetry 1997, 8, 3717. (p) Veeresa, G.; Dutta, A. Tetrahedron Lett. 1998, 39, 119.
71. For the synthesis of natural and unnatural polyoxamic acid, see: (a) Kuzuhara, H.; Emoto, S. Tetrahedron Lett. 1973, 5051. (b) Kuzuhara, H.; Kimura, M.; Emoto, S. Carbohydr. Res. 1975, 45, 245. (c) Saksena, A. K.; Lovey, R. G.; Girijavallabhan, V. M.; Ganguly, A. K. J. Org. Chem. 1986, 51, 5024. (d) Hirama, H.; Hioku, H.; Ito, S. Tetrahedron Lett. 1988, 29, 3125. (e) Garner, P.; Park, J. M. J. Org. Chem. 1988, 53, 2979. (f) Savage, I.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1989, 717. (g) Dureault, A.; Carreaux, F.; Depezay, J. C. Synthesis 1990, 46, 265. (h) Paz, M. M.; Sardina, F. J. J. Org. Chem. 1993, 58, 6990. (i) Dondini, A.; Franco, S.; Merchan, F. L.; Merino, P.; Tejero, T. Tetrahedron Lett. 1993, 34, 5479. (j) Matsura, F.; Hamada, Y.; Shioroi, T. Tetrahedron Lett. 1994, 35, 733. (k) Marshall, J. A.; Seletsky, B. M.; Coan, P. S. J. Org. Chem. 1994, 59, 5139. (l) Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. Org. Chem. 1995, 60, 6431. (m) Kang, S. H.; Choi, H. W. Chem Commun. 1996, 1521. (n) Trost, B. M.; Krueger, A. C.; Bunt, R. C., Zombrano, J. J. Am. Chem. Soc. 1996, 118, 6520. (o) Bandini, E.; Martelli, G.; Spunta, G.; Borgini, A.; Panuzio, M.; Piersanti, G. Tetrahedron: Asymmetry 1997, 8, 3717. (p) Veeresa, G.; Dutta, A. Tetrahedron Lett. 1998, 39, 119.
72. For the synthesis of natural and unnatural polyoxamic acid, see: (a) Kuzuhara, H.; Emoto, S. Tetrahedron Lett. 1973, 5051. (b) Kuzuhara, H.; Kimura, M.; Emoto, S. Carbohydr. Res. 1975, 45, 245. (c) Saksena, A. K.; Lovey, R. G.; Girijavallabhan, V. M.; Ganguly, A. K. J. Org. Chem. 1986, 51, 5024. (d) Hirama, H.; Hioku, H.; Ito, S. Tetrahedron Lett. 1988, 29, 3125. (e) Garner, P.; Park, J. M. J. Org. Chem. 1988, 53, 2979. (f) Savage, I.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1989, 717. (g) Dureault, A.; Carreaux, F.; Depezay, J. C. Synthesis 1990, 46, 265. (h) Paz, M. M.; Sardina, F. J. J. Org. Chem. 1993, 58, 6990. (i) Dondini, A.; Franco, S.; Merchan, F. L.; Merino, P.; Tejero, T. Tetrahedron Lett. 1993, 34, 5479. (j) Matsura, F.; Hamada, Y.; Shioroi, T. Tetrahedron Lett. 1994, 35, 733. (k) Marshall, J. A.; Seletsky, B. M.; Coan, P. S. J. Org. Chem. 1994, 59, 5139. (l) Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. Org. Chem. 1995, 60, 6431. (m) Kang, S. H.; Choi, H. W. Chem Commun. 1996, 1521. (n) Trost, B. M.; Krueger, A. C.; Bunt, R. C., Zombrano, J. J. Am. Chem. Soc. 1996, 118, 6520. (o) Bandini, E.; Martelli, G.; Spunta, G.; Borgini, A.; Panuzio, M.; Piersanti, G. Tetrahedron: Asymmetry 1997, 8, 3717. (p) Veeresa, G.; Dutta, A. Tetrahedron Lett. 1998, 39, 119.
73. For the synthesis of natural and unnatural polyoxamic acid, see: (a) Kuzuhara, H.; Emoto, S. Tetrahedron Lett. 1973, 5051. (b) Kuzuhara, H.; Kimura, M.; Emoto, S. Carbohydr. Res. 1975, 45, 245. (c) Saksena, A. K.; Lovey, R. G.; Girijavallabhan, V. M.; Ganguly, A. K. J. Org. Chem. 1986, 51, 5024. (d) Hirama, H.; Hioku, H.; Ito, S. Tetrahedron Lett. 1988, 29, 3125. (e) Garner, P.; Park, J. M. J. Org. Chem. 1988, 53, 2979. (f) Savage, I.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1989, 717. (g) Dureault, A.; Carreaux, F.; Depezay, J. C. Synthesis 1990, 46, 265. (h) Paz, M. M.; Sardina, F. J. J. Org. Chem. 1993, 58, 6990. (i) Dondini, A.; Franco, S.; Merchan, F. L.; Merino, P.; Tejero, T. Tetrahedron Lett. 1993, 34, 5479. (j) Matsura, F.; Hamada, Y.; Shioroi, T. Tetrahedron Lett. 1994, 35, 733. (k) Marshall, J. A.; Seletsky, B. M.; Coan, P. S. J. Org. Chem. 1994, 59, 5139. (l) Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. Org. Chem. 1995, 60, 6431. (m) Kang, S. H.; Choi, H. W. Chem Commun. 1996, 1521. (n) Trost, B. M.; Krueger, A. C.; Bunt, R. C., Zombrano, J. J. Am. Chem. Soc. 1996, 118, 6520. (o) Bandini, E.; Martelli, G.; Spunta, G.; Borgini, A.; Panuzio, M.; Piersanti, G. Tetrahedron: Asymmetry 1997, 8, 3717. (p) Veeresa, G.; Dutta, A. Tetrahedron Lett. 1998, 39, 119.
74. For the synthesis of natural and unnatural polyoxamic acid, see: (a) Kuzuhara, H.; Emoto, S. Tetrahedron Lett. 1973, 5051. (b) Kuzuhara, H.; Kimura, M.; Emoto, S. Carbohydr. Res. 1975, 45, 245. (c) Saksena, A. K.; Lovey, R. G.; Girijavallabhan, V. M.; Ganguly, A. K. J. Org. Chem. 1986, 51, 5024. (d) Hirama, H.; Hioku, H.; Ito, S. Tetrahedron Lett. 1988, 29, 3125. (e) Garner, P.; Park, J. M. J. Org. Chem. 1988, 53, 2979. (f) Savage, I.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1989, 717. (g) Dureault, A.; Carreaux, F.; Depezay, J. C. Synthesis 1990, 46, 265. (h) Paz, M. M.; Sardina, F. J. J. Org. Chem. 1993, 58, 6990. (i) Dondini, A.; Franco, S.; Merchan, F. L.; Merino, P.; Tejero, T. Tetrahedron Lett. 1993, 34, 5479. (j) Matsura, F.; Hamada, Y.; Shioroi, T. Tetrahedron Lett. 1994, 35, 733. (k) Marshall, J. A.; Seletsky, B. M.; Coan, P. S. J. Org. Chem. 1994, 59, 5139. (l) Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. Org. Chem. 1995, 60, 6431. (m) Kang, S. H.; Choi, H. W. Chem Commun. 1996, 1521. (n) Trost, B. M.; Krueger, A. C.; Bunt, R. C., Zombrano, J. J. Am. Chem. Soc. 1996, 118, 6520. (o) Bandini, E.; Martelli, G.; Spunta, G.; Borgini, A.; Panuzio, M.; Piersanti, G. Tetrahedron: Asymmetry 1997, 8, 3717. (p) Veeresa, G.; Dutta, A. Tetrahedron Lett. 1998, 39, 119.
75. For the synthesis of natural and unnatural polyoxamic acid, see: (a) Kuzuhara, H.; Emoto, S. Tetrahedron Lett. 1973, 5051. (b) Kuzuhara, H.; Kimura, M.; Emoto, S. Carbohydr. Res. 1975, 45, 245. (c) Saksena, A. K.; Lovey, R. G.; Girijavallabhan, V. M.; Ganguly, A. K. J. Org. Chem. 1986, 51, 5024. (d) Hirama, H.; Hioku, H.; Ito, S. Tetrahedron Lett. 1988, 29, 3125. (e) Garner, P.; Park, J. M. J. Org. Chem. 1988, 53, 2979. (f) Savage, I.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1989, 717. (g) Dureault, A.; Carreaux, F.; Depezay, J. C. Synthesis 1990, 46, 265. (h) Paz, M. M.; Sardina, F. J. J. Org. Chem. 1993, 58, 6990. (i) Dondini, A.; Franco, S.; Merchan, F. L.; Merino, P.; Tejero, T. Tetrahedron Lett. 1993, 34, 5479. (j) Matsura, F.; Hamada, Y.; Shioroi, T. Tetrahedron Lett. 1994, 35, 733. (k) Marshall, J. A.; Seletsky, B. M.; Coan, P. S. J. Org. Chem. 1994, 59, 5139. (l) Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. Org. Chem. 1995, 60, 6431. (m) Kang, S. H.; Choi, H. W. Chem Commun. 1996, 1521. (n) Trost, B. M.; Krueger, A. C.; Bunt, R. C., Zombrano, J. J. Am. Chem. Soc. 1996, 118, 6520. (o) Bandini, E.; Martelli, G.; Spunta, G.; Borgini, A.; Panuzio, M.; Piersanti, G. Tetrahedron: Asymmetry 1997, 8, 3717. (p) Veeresa, G.; Dutta, A. Tetrahedron Lett. 1998, 39, 119.
76. For the synthesis of natural and unnatural polyoxamic acid, see: (a) Kuzuhara, H.; Emoto, S. Tetrahedron Lett. 1973, 5051. (b) Kuzuhara, H.; Kimura, M.; Emoto, S. Carbohydr. Res. 1975, 45, 245. (c) Saksena, A. K.; Lovey, R. G.; Girijavallabhan, V. M.; Ganguly, A. K. J. Org. Chem. 1986, 51, 5024. (d) Hirama, H.; Hioku, H.; Ito, S. Tetrahedron Lett. 1988, 29, 3125. (e) Garner, P.; Park, J. M. J. Org. Chem. 1988, 53, 2979. (f) Savage, I.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1989, 717. (g) Dureault, A.; Carreaux, F.; Depezay, J. C. Synthesis 1990, 46, 265. (h) Paz, M. M.; Sardina, F. J. J. Org. Chem. 1993, 58, 6990. (i) Dondini, A.; Franco, S.; Merchan, F. L.; Merino, P.; Tejero, T. Tetrahedron Lett. 1993, 34, 5479. (j) Matsura, F.; Hamada, Y.; Shioroi, T. Tetrahedron Lett. 1994, 35, 733. (k) Marshall, J. A.; Seletsky, B. M.; Coan, P. S. J. Org. Chem. 1994, 59, 5139. (l) Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. Org. Chem. 1995, 60, 6431. (m) Kang, S. H.; Choi, H. W. Chem Commun. 1996, 1521. (n) Trost, B. M.; Krueger, A. C.; Bunt, R. C., Zombrano, J. J. Am. Chem. Soc. 1996, 118, 6520. (o) Bandini, E.; Martelli, G.; Spunta, G.; Borgini, A.; Panuzio, M.; Piersanti, G. Tetrahedron: Asymmetry 1997, 8, 3717. (p) Veeresa, G.; Dutta, A. Tetrahedron Lett. 1998, 39, 119.
77. For the synthesis of natural and unnatural polyoxamic acid, see: (a) Kuzuhara, H.; Emoto, S. Tetrahedron Lett. 1973, 5051. (b) Kuzuhara, H.; Kimura, M.; Emoto, S. Carbohydr. Res. 1975, 45, 245. (c) Saksena, A. K.; Lovey, R. G.; Girijavallabhan, V. M.; Ganguly, A. K. J. Org. Chem. 1986, 51, 5024. (d) Hirama, H.; Hioku, H.; Ito, S. Tetrahedron Lett. 1988, 29, 3125. (e) Garner, P.; Park, J. M. J. Org. Chem. 1988, 53, 2979. (f) Savage, I.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1989, 717. (g) Dureault, A.; Carreaux, F.; Depezay, J. C. Synthesis 1990, 46, 265. (h) Paz, M. M.; Sardina, F. J. J. Org. Chem. 1993, 58, 6990. (i) Dondini, A.; Franco, S.; Merchan, F. L.; Merino, P.; Tejero, T. Tetrahedron Lett. 1993, 34, 5479. (j) Matsura, F.; Hamada, Y.; Shioroi, T. Tetrahedron Lett. 1994, 35, 733. (k) Marshall, J. A.; Seletsky, B. M.; Coan, P. S. J. Org. Chem. 1994, 59, 5139. (l) Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. Org. Chem. 1995, 60, 6431. (m) Kang, S. H.; Choi, H. W. Chem Commun. 1996, 1521. (n) Trost, B. M.; Krueger, A. C.; Bunt, R. C., Zombrano, J. J. Am. Chem. Soc. 1996, 118, 6520. (o) Bandini, E.; Martelli, G.; Spunta, G.; Borgini, A.; Panuzio, M.; Piersanti, G. Tetrahedron: Asymmetry 1997, 8, 3717. (p) Veeresa, G.; Dutta, A. Tetrahedron Lett. 1998, 39, 119.
78. For the synthesis of natural and unnatural polyoxamic acid, see: (a) Kuzuhara, H.; Emoto, S. Tetrahedron Lett. 1973, 5051. (b) Kuzuhara, H.; Kimura, M.; Emoto, S. Carbohydr. Res. 1975, 45, 245. (c) Saksena, A. K.; Lovey, R. G.; Girijavallabhan, V. M.; Ganguly, A. K. J. Org. Chem. 1986, 51, 5024. (d) Hirama, H.; Hioku, H.; Ito, S. Tetrahedron Lett. 1988, 29, 3125. (e) Garner, P.; Park, J. M. J. Org. Chem. 1988, 53, 2979. (f) Savage, I.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1989, 717. (g) Dureault, A.; Carreaux, F.; Depezay, J. C. Synthesis 1990, 46, 265. (h) Paz, M. M.; Sardina, F. J. J. Org. Chem. 1993, 58, 6990. (i) Dondini, A.; Franco, S.; Merchan, F. L.; Merino, P.; Tejero, T. Tetrahedron Lett. 1993, 34, 5479. (j) Matsura, F.; Hamada, Y.; Shioroi, T. Tetrahedron Lett. 1994, 35, 733. (k) Marshall, J. A.; Seletsky, B. M.; Coan, P. S. J. Org. Chem. 1994, 59, 5139. (l) Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. Org. Chem. 1995, 60, 6431. (m) Kang, S. H.; Choi, H. W. Chem Commun. 1996, 1521. (n) Trost, B. M.; Krueger, A. C.; Bunt, R. C., Zombrano, J. J. Am. Chem. Soc. 1996, 118, 6520. (o) Bandini, E.; Martelli, G.; Spunta, G.; Borgini, A.; Panuzio, M.; Piersanti, G. Tetrahedron: Asymmetry 1997, 8, 3717. (p) Veeresa, G.; Dutta, A. Tetrahedron Lett. 1998, 39, 119.
79. For the synthesis of natural and unnatural polyoxamic acid, see: (a) Kuzuhara, H.; Emoto, S. Tetrahedron Lett. 1973, 5051. (b) Kuzuhara, H.; Kimura, M.; Emoto, S. Carbohydr. Res. 1975, 45, 245. (c) Saksena, A. K.; Lovey, R. G.; Girijavallabhan, V. M.; Ganguly, A. K. J. Org. Chem. 1986, 51, 5024. (d) Hirama, H.; Hioku, H.; Ito, S. Tetrahedron Lett. 1988, 29, 3125. (e) Garner, P.; Park, J. M. J. Org. Chem. 1988, 53, 2979. (f) Savage, I.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1989, 717. (g) Dureault, A.; Carreaux, F.; Depezay, J. C. Synthesis 1990, 46, 265. (h) Paz, M. M.; Sardina, F. J. J. Org. Chem. 1993, 58, 6990. (i) Dondini, A.; Franco, S.; Merchan, F. L.; Merino, P.; Tejero, T. Tetrahedron Lett. 1993, 34, 5479. (j) Matsura, F.; Hamada, Y.; Shioroi, T. Tetrahedron Lett. 1994, 35, 733. (k) Marshall, J. A.; Seletsky, B. M.; Coan, P. S. J. Org. Chem. 1994, 59, 5139. (l) Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. Org. Chem. 1995, 60, 6431. (m) Kang, S. H.; Choi, H. W. Chem Commun. 1996, 1521. (n) Trost, B. M.; Krueger, A. C.; Bunt, R. C., Zombrano, J. J. Am. Chem. Soc. 1996, 118, 6520. (o) Bandini, E.; Martelli, G.; Spunta, G.; Borgini, A.; Panuzio, M.; Piersanti, G. Tetrahedron: Asymmetry 1997, 8, 3717. (p) Veeresa, G.; Dutta, A. Tetrahedron Lett. 1998, 39, 119.
80. For the synthesis of natural and unnatural polyoxamic acid, see: (a) Kuzuhara, H.; Emoto, S. Tetrahedron Lett. 1973, 5051. (b) Kuzuhara, H.; Kimura, M.; Emoto, S. Carbohydr. Res. 1975, 45, 245. (c) Saksena, A. K.; Lovey, R. G.; Girijavallabhan, V. M.; Ganguly, A. K. J. Org. Chem. 1986, 51, 5024. (d) Hirama, H.; Hioku, H.; Ito, S. Tetrahedron Lett. 1988, 29, 3125. (e) Garner, P.; Park, J. M. J. Org. Chem. 1988, 53, 2979. (f) Savage, I.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1989, 717. (g) Dureault, A.; Carreaux, F.; Depezay, J. C. Synthesis 1990, 46, 265. (h) Paz, M. M.; Sardina, F. J. J. Org. Chem. 1993, 58, 6990. (i) Dondini, A.; Franco, S.; Merchan, F. L.; Merino, P.; Tejero, T. Tetrahedron Lett. 1993, 34, 5479. (j) Matsura, F.; Hamada, Y.; Shioroi, T. Tetrahedron Lett. 1994, 35, 733. (k) Marshall, J. A.; Seletsky, B. M.; Coan, P. S. J. Org. Chem. 1994, 59, 5139. (l) Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. Org. Chem. 1995, 60, 6431. (m) Kang, S. H.; Choi, H. W. Chem Commun. 1996, 1521. (n) Trost, B. M.; Krueger, A. C.; Bunt, R. C., Zombrano, J. J. Am. Chem. Soc. 1996, 118, 6520. (o) Bandini, E.; Martelli, G.; Spunta, G.; Borgini, A.; Panuzio, M.; Piersanti, G. Tetrahedron: Asymmetry 1997, 8, 3717. (p) Veeresa, G.; Dutta, A. Tetrahedron Lett. 1998, 39, 119.
81. Banik B.K., Manhas M.S., Bose A.K. J. Org. Chem. 58:1993;307.
82. The structure and stereochemistry were confirmed by single crystal X-ray diffraction study of a related β-lactam. For example, see: Pain, S.; Biswas, G.; Bose, A.K.; Banerjee, A. Acta Cryst. 1992, C48, 666.
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86. Varma R.S., Dahiya R., Kumar S. Tetrahedron Lett. 38:1997;2039.
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