Synthetic studies towards peptidyl nucleoside antibiotics: First synthesis of a polyoxamic acid derivative enabling direct coupling with α-amino acid esters

Chemical Communications

Volumn , Issue 7, 1997, Pages 691-692

  Palomo, Claudio ^a   Oiarbide, Mikel ^a   Esnal, Aitor ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACID ANHYDRIDE; ALDEHYDE; AMINO ACID; ANTIBIOTIC AGENT; BETA LACTAM; IMINE; KETOL; NUCLEOSIDE ANALOG; POLYOXAMIC ACID DERIVATIVE; TEMPONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS;

EID: 0030947166     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a700815e     Document Type: Article

References (29)

1. For reviews on this subject, see K. Isono, J. Antibiot., 1988, 41, 1711; K. Isono, Pharm. Ther., 1991, 52, 269.
2. For reviews on this subject, see K. Isono, J. Antibiot., 1988, 41, 1711; K. Isono, Pharm. Ther., 1991, 52, 269.
3. A. B. Cooper, J. Desai, R. G. Lovey, A. K. Saksena, V. M. Girijavallabhan, A. K. Ganguly, D. Loebenberg, R. Parmegiani and A. Cacciapuoti, Bioorg. Med. Chem. Lett., 1993, 3, 1079 and references cited therein.
4. For reviews, see (a) P. Garner, in Studies in Natural Products Chemistry, ed. Atta-Ur Rahman, Elsevier, Amsterdam, 1988, vol. 1, part A, p. 397; (b) G. Casiraghi, F. Zanardi, G. Rassu and P. Spanu, Chem. Rev., 1995, 95, 1677. For recent methods, see (c) A. K. Saksena, R. G. Lovey, V. M. Girigavallabhan and A. K. Ganguly, J. Org. Chem., 1986, 51, 5024; (d) I. Savage and E. J. Thomas, J. Chem. Soc., Chem. Commun., 1989, 717; (e) T. Mukaiyama, K. Suzuki, T. Yamada and F. Tabuga, Tetrahedron, 1990, 46, 265; (f) A. Dondoni, S. Franco, F. L. Merchán, P. Merino and T. Tejero, Tetrahedron Lett., 1993, 34, 5479; (g) R. F. W. Jackson, N. J. Palmer, M. J. Wythes, W. Clegg and M. R. J. Elsegood, J. Org. Chem., 1995, 60, 6431; (h) P. Garner and J. M. Park, J. Org. Chem., 1988, 53, 2979; (i) A. Dureault, F. Carreaux and J. C. Depezay, Synthesis, 1991, 150; (j) M. Irama, H. Hioki and S. Ito, Tetrahedron Lett., 1988, 29, 3125; (k) B. K. Banik, M. S. Manhas and A. K. Bose, J. Org. Chem., 1993, 58, 307; (l) M. M. Paz and F. J. Sardina, J. Org. Chem., 1993, 58, 6990; (m) F. Matsuura, Y. Hamada and T. Shiori, Tetrahedron Lett., 1994, 35, 733; (n) B. M. Trost, A. C. Krueger, R. C. Bunt and J. Zambrano, J. Am. Chem. Soc., 1996, 118, 6520; (o) S. H. Kang and H.-W. Choi, Chem. Commun., 1996, 1521.
5. For reviews, see (a) P. Garner, in Studies in Natural Products Chemistry, ed. Atta-Ur Rahman, Elsevier, Amsterdam, 1988, vol. 1, part A, p. 397; (b) G. Casiraghi, F. Zanardi, G. Rassu and P. Spanu, Chem. Rev., 1995, 95, 1677. For recent methods, see (c) A. K. Saksena, R. G. Lovey, V. M. Girigavallabhan and A. K. Ganguly, J. Org. Chem., 1986, 51, 5024; (d) I. Savage and E. J. Thomas, J. Chem. Soc., Chem. Commun., 1989, 717; (e) T. Mukaiyama, K. Suzuki, T. Yamada and F. Tabuga, Tetrahedron, 1990, 46, 265; (f) A. Dondoni, S. Franco, F. L. Merchán, P. Merino and T. Tejero, Tetrahedron Lett., 1993, 34, 5479; (g) R. F. W. Jackson, N. J. Palmer, M. J. Wythes, W. Clegg and M. R. J. Elsegood, J. Org. Chem., 1995, 60, 6431; (h) P. Garner and J. M. Park, J. Org. Chem., 1988, 53, 2979; (i) A. Dureault, F. Carreaux and J. C. Depezay, Synthesis, 1991, 150; (j) M. Irama, H. Hioki and S. Ito, Tetrahedron Lett., 1988, 29, 3125; (k) B. K. Banik, M. S. Manhas and A. K. Bose, J. Org. Chem., 1993, 58, 307; (l) M. M. Paz and F. J. Sardina, J. Org. Chem., 1993, 58, 6990; (m) F. Matsuura, Y. Hamada and T. Shiori, Tetrahedron Lett., 1994, 35, 733; (n) B. M. Trost, A. C. Krueger, R. C. Bunt and J. Zambrano, J. Am. Chem. Soc., 1996, 118, 6520; (o) S. H. Kang and H.-W. Choi, Chem. Commun., 1996, 1521.
6. For reviews, see (a) P. Garner, in Studies in Natural Products Chemistry, ed. Atta-Ur Rahman, Elsevier, Amsterdam, 1988, vol. 1, part A, p. 397; (b) G. Casiraghi, F. Zanardi, G. Rassu and P. Spanu, Chem. Rev., 1995, 95, 1677. For recent methods, see (c) A. K. Saksena, R. G. Lovey, V. M. Girigavallabhan and A. K. Ganguly, J. Org. Chem., 1986, 51, 5024; (d) I. Savage and E. J. Thomas, J. Chem. Soc., Chem. Commun., 1989, 717; (e) T. Mukaiyama, K. Suzuki, T. Yamada and F. Tabuga, Tetrahedron, 1990, 46, 265; (f) A. Dondoni, S. Franco, F. L. Merchán, P. Merino and T. Tejero, Tetrahedron Lett., 1993, 34, 5479; (g) R. F. W. Jackson, N. J. Palmer, M. J. Wythes, W. Clegg and M. R. J. Elsegood, J. Org. Chem., 1995, 60, 6431; (h) P. Garner and J. M. Park, J. Org. Chem., 1988, 53, 2979; (i) A. Dureault, F. Carreaux and J. C. Depezay, Synthesis, 1991, 150; (j) M. Irama, H. Hioki and S. Ito, Tetrahedron Lett., 1988, 29, 3125; (k) B. K. Banik, M. S. Manhas and A. K. Bose, J. Org. Chem., 1993, 58, 307; (l) M. M. Paz and F. J. Sardina, J. Org. Chem., 1993, 58, 6990; (m) F. Matsuura, Y. Hamada and T. Shiori, Tetrahedron Lett., 1994, 35, 733; (n) B. M. Trost, A. C. Krueger, R. C. Bunt and J. Zambrano, J. Am. Chem. Soc., 1996, 118, 6520; (o) S. H. Kang and H.-W. Choi, Chem. Commun., 1996, 1521.
7. For reviews, see (a) P. Garner, in Studies in Natural Products Chemistry, ed. Atta-Ur Rahman, Elsevier, Amsterdam, 1988, vol. 1, part A, p. 397; (b) G. Casiraghi, F. Zanardi, G. Rassu and P. Spanu, Chem. Rev., 1995, 95, 1677. For recent methods, see (c) A. K. Saksena, R. G. Lovey, V. M. Girigavallabhan and A. K. Ganguly, J. Org. Chem., 1986, 51, 5024; (d) I. Savage and E. J. Thomas, J. Chem. Soc., Chem. Commun., 1989, 717; (e) T. Mukaiyama, K. Suzuki, T. Yamada and F. Tabuga, Tetrahedron, 1990, 46, 265; (f) A. Dondoni, S. Franco, F. L. Merchán, P. Merino and T. Tejero, Tetrahedron Lett., 1993, 34, 5479; (g) R. F. W. Jackson, N. J. Palmer, M. J. Wythes, W. Clegg and M. R. J. Elsegood, J. Org. Chem., 1995, 60, 6431; (h) P. Garner and J. M. Park, J. Org. Chem., 1988, 53, 2979; (i) A. Dureault, F. Carreaux and J. C. Depezay, Synthesis, 1991, 150; (j) M. Irama, H. Hioki and S. Ito, Tetrahedron Lett., 1988, 29, 3125; (k) B. K. Banik, M. S. Manhas and A. K. Bose, J. Org. Chem., 1993, 58, 307; (l) M. M. Paz and F. J. Sardina, J. Org. Chem., 1993, 58, 6990; (m) F. Matsuura, Y. Hamada and T. Shiori, Tetrahedron Lett., 1994, 35, 733; (n) B. M. Trost, A. C. Krueger, R. C. Bunt and J. Zambrano, J. Am. Chem. Soc., 1996, 118, 6520; (o) S. H. Kang and H.-W. Choi, Chem. Commun., 1996, 1521.
8. For reviews, see (a) P. Garner, in Studies in Natural Products Chemistry, ed. Atta-Ur Rahman, Elsevier, Amsterdam, 1988, vol. 1, part A, p. 397; (b) G. Casiraghi, F. Zanardi, G. Rassu and P. Spanu, Chem. Rev., 1995, 95, 1677. For recent methods, see (c) A. K. Saksena, R. G. Lovey, V. M. Girigavallabhan and A. K. Ganguly, J. Org. Chem., 1986, 51, 5024; (d) I. Savage and E. J. Thomas, J. Chem. Soc., Chem. Commun., 1989, 717; (e) T. Mukaiyama, K. Suzuki, T. Yamada and F. Tabuga, Tetrahedron, 1990, 46, 265; (f) A. Dondoni, S. Franco, F. L. Merchán, P. Merino and T. Tejero, Tetrahedron Lett., 1993, 34, 5479; (g) R. F. W. Jackson, N. J. Palmer, M. J. Wythes, W. Clegg and M. R. J. Elsegood, J. Org. Chem., 1995, 60, 6431; (h) P. Garner and J. M. Park, J. Org. Chem., 1988, 53, 2979; (i) A. Dureault, F. Carreaux and J. C. Depezay, Synthesis, 1991, 150; (j) M. Irama, H. Hioki and S. Ito, Tetrahedron Lett., 1988, 29, 3125; (k) B. K. Banik, M. S. Manhas and A. K. Bose, J. Org. Chem., 1993, 58, 307; (l) M. M. Paz and F. J. Sardina, J. Org. Chem., 1993, 58, 6990; (m) F. Matsuura, Y. Hamada and T. Shiori, Tetrahedron Lett., 1994, 35, 733; (n) B. M. Trost, A. C. Krueger, R. C. Bunt and J. Zambrano, J. Am. Chem. Soc., 1996, 118, 6520; (o) S. H. Kang and H.-W. Choi, Chem. Commun., 1996, 1521.
9. For reviews, see (a) P. Garner, in Studies in Natural Products Chemistry, ed. Atta-Ur Rahman, Elsevier, Amsterdam, 1988, vol. 1, part A, p. 397; (b) G. Casiraghi, F. Zanardi, G. Rassu and P. Spanu, Chem. Rev., 1995, 95, 1677. For recent methods, see (c) A. K. Saksena, R. G. Lovey, V. M. Girigavallabhan and A. K. Ganguly, J. Org. Chem., 1986, 51, 5024; (d) I. Savage and E. J. Thomas, J. Chem. Soc., Chem. Commun., 1989, 717; (e) T. Mukaiyama, K. Suzuki, T. Yamada and F. Tabuga, Tetrahedron, 1990, 46, 265; (f) A. Dondoni, S. Franco, F. L. Merchán, P. Merino and T. Tejero, Tetrahedron Lett., 1993, 34, 5479; (g) R. F. W. Jackson, N. J. Palmer, M. J. Wythes, W. Clegg and M. R. J. Elsegood, J. Org. Chem., 1995, 60, 6431; (h) P. Garner and J. M. Park, J. Org. Chem., 1988, 53, 2979; (i) A. Dureault, F. Carreaux and J. C. Depezay, Synthesis, 1991, 150; (j) M. Irama, H. Hioki and S. Ito, Tetrahedron Lett., 1988, 29, 3125; (k) B. K. Banik, M. S. Manhas and A. K. Bose, J. Org. Chem., 1993, 58, 307; (l) M. M. Paz and F. J. Sardina, J. Org. Chem., 1993, 58, 6990; (m) F. Matsuura, Y. Hamada and T. Shiori, Tetrahedron Lett., 1994, 35, 733; (n) B. M. Trost, A. C. Krueger, R. C. Bunt and J. Zambrano, J. Am. Chem. Soc., 1996, 118, 6520; (o) S. H. Kang and H.-W. Choi, Chem. Commun., 1996, 1521.
10. For reviews, see (a) P. Garner, in Studies in Natural Products Chemistry, ed. Atta-Ur Rahman, Elsevier, Amsterdam, 1988, vol. 1, part A, p. 397; (b) G. Casiraghi, F. Zanardi, G. Rassu and P. Spanu, Chem. Rev., 1995, 95, 1677. For recent methods, see (c) A. K. Saksena, R. G. Lovey, V. M. Girigavallabhan and A. K. Ganguly, J. Org. Chem., 1986, 51, 5024; (d) I. Savage and E. J. Thomas, J. Chem. Soc., Chem. Commun., 1989, 717; (e) T. Mukaiyama, K. Suzuki, T. Yamada and F. Tabuga, Tetrahedron, 1990, 46, 265; (f) A. Dondoni, S. Franco, F. L. Merchán, P. Merino and T. Tejero, Tetrahedron Lett., 1993, 34, 5479; (g) R. F. W. Jackson, N. J. Palmer, M. J. Wythes, W. Clegg and M. R. J. Elsegood, J. Org. Chem., 1995, 60, 6431; (h) P. Garner and J. M. Park, J. Org. Chem., 1988, 53, 2979; (i) A. Dureault, F. Carreaux and J. C. Depezay, Synthesis, 1991, 150; (j) M. Irama, H. Hioki and S. Ito, Tetrahedron Lett., 1988, 29, 3125; (k) B. K. Banik, M. S. Manhas and A. K. Bose, J. Org. Chem., 1993, 58, 307; (l) M. M. Paz and F. J. Sardina, J. Org. Chem., 1993, 58, 6990; (m) F. Matsuura, Y. Hamada and T. Shiori, Tetrahedron Lett., 1994, 35, 733; (n) B. M. Trost, A. C. Krueger, R. C. Bunt and J. Zambrano, J. Am. Chem. Soc., 1996, 118, 6520; (o) S. H. Kang and H.-W. Choi, Chem. Commun., 1996, 1521.
11. For reviews, see (a) P. Garner, in Studies in Natural Products Chemistry, ed. Atta-Ur Rahman, Elsevier, Amsterdam, 1988, vol. 1, part A, p. 397; (b) G. Casiraghi, F. Zanardi, G. Rassu and P. Spanu, Chem. Rev., 1995, 95, 1677. For recent methods, see (c) A. K. Saksena, R. G. Lovey, V. M. Girigavallabhan and A. K. Ganguly, J. Org. Chem., 1986, 51, 5024; (d) I. Savage and E. J. Thomas, J. Chem. Soc., Chem. Commun., 1989, 717; (e) T. Mukaiyama, K. Suzuki, T. Yamada and F. Tabuga, Tetrahedron, 1990, 46, 265; (f) A. Dondoni, S. Franco, F. L. Merchán, P. Merino and T. Tejero, Tetrahedron Lett., 1993, 34, 5479; (g) R. F. W. Jackson, N. J. Palmer, M. J. Wythes, W. Clegg and M. R. J. Elsegood, J. Org. Chem., 1995, 60, 6431; (h) P. Garner and J. M. Park, J. Org. Chem., 1988, 53, 2979; (i) A. Dureault, F. Carreaux and J. C. Depezay, Synthesis, 1991, 150; (j) M. Irama, H. Hioki and S. Ito, Tetrahedron Lett., 1988, 29, 3125; (k) B. K. Banik, M. S. Manhas and A. K. Bose, J. Org. Chem., 1993, 58, 307; (l) M. M. Paz and F. J. Sardina, J. Org. Chem., 1993, 58, 6990; (m) F. Matsuura, Y. Hamada and T. Shiori, Tetrahedron Lett., 1994, 35, 733; (n) B. M. Trost, A. C. Krueger, R. C. Bunt and J. Zambrano, J. Am. Chem. Soc., 1996, 118, 6520; (o) S. H. Kang and H.-W. Choi, Chem. Commun., 1996, 1521.
12. For reviews, see (a) P. Garner, in Studies in Natural Products Chemistry, ed. Atta-Ur Rahman, Elsevier, Amsterdam, 1988, vol. 1, part A, p. 397; (b) G. Casiraghi, F. Zanardi, G. Rassu and P. Spanu, Chem. Rev., 1995, 95, 1677. For recent methods, see (c) A. K. Saksena, R. G. Lovey, V. M. Girigavallabhan and A. K. Ganguly, J. Org. Chem., 1986, 51, 5024; (d) I. Savage and E. J. Thomas, J. Chem. Soc., Chem. Commun., 1989, 717; (e) T. Mukaiyama, K. Suzuki, T. Yamada and F. Tabuga, Tetrahedron, 1990, 46, 265; (f) A. Dondoni, S. Franco, F. L. Merchán, P. Merino and T. Tejero, Tetrahedron Lett., 1993, 34, 5479; (g) R. F. W. Jackson, N. J. Palmer, M. J. Wythes, W. Clegg and M. R. J. Elsegood, J. Org. Chem., 1995, 60, 6431; (h) P. Garner and J. M. Park, J. Org. Chem., 1988, 53, 2979; (i) A. Dureault, F. Carreaux and J. C. Depezay, Synthesis, 1991, 150; (j) M. Irama, H. Hioki and S. Ito, Tetrahedron Lett., 1988, 29, 3125; (k) B. K. Banik, M. S. Manhas and A. K. Bose, J. Org. Chem., 1993, 58, 307; (l) M. M. Paz and F. J. Sardina, J. Org. Chem., 1993, 58, 6990; (m) F. Matsuura, Y. Hamada and T. Shiori, Tetrahedron Lett., 1994, 35, 733; (n) B. M. Trost, A. C. Krueger, R. C. Bunt and J. Zambrano, J. Am. Chem. Soc., 1996, 118, 6520; (o) S. H. Kang and H.-W. Choi, Chem. Commun., 1996, 1521.
13. For reviews, see (a) P. Garner, in Studies in Natural Products Chemistry, ed. Atta-Ur Rahman, Elsevier, Amsterdam, 1988, vol. 1, part A, p. 397; (b) G. Casiraghi, F. Zanardi, G. Rassu and P. Spanu, Chem. Rev., 1995, 95, 1677. For recent methods, see (c) A. K. Saksena, R. G. Lovey, V. M. Girigavallabhan and A. K. Ganguly, J. Org. Chem., 1986, 51, 5024; (d) I. Savage and E. J. Thomas, J. Chem. Soc., Chem. Commun., 1989, 717; (e) T. Mukaiyama, K. Suzuki, T. Yamada and F. Tabuga, Tetrahedron, 1990, 46, 265; (f) A. Dondoni, S. Franco, F. L. Merchán, P. Merino and T. Tejero, Tetrahedron Lett., 1993, 34, 5479; (g) R. F. W. Jackson, N. J. Palmer, M. J. Wythes, W. Clegg and M. R. J. Elsegood, J. Org. Chem., 1995, 60, 6431; (h) P. Garner and J. M. Park, J. Org. Chem., 1988, 53, 2979; (i) A. Dureault, F. Carreaux and J. C. Depezay, Synthesis, 1991, 150; (j) M. Irama, H. Hioki and S. Ito, Tetrahedron Lett., 1988, 29, 3125; (k) B. K. Banik, M. S. Manhas and A. K. Bose, J. Org. Chem., 1993, 58, 307; (l) M. M. Paz and F. J. Sardina, J. Org. Chem., 1993, 58, 6990; (m) F. Matsuura, Y. Hamada and T. Shiori, Tetrahedron Lett., 1994, 35, 733; (n) B. M. Trost, A. C. Krueger, R. C. Bunt and J. Zambrano, J. Am. Chem. Soc., 1996, 118, 6520; (o) S. H. Kang and H.-W. Choi, Chem. Commun., 1996, 1521.
14. For reviews, see (a) P. Garner, in Studies in Natural Products Chemistry, ed. Atta-Ur Rahman, Elsevier, Amsterdam, 1988, vol. 1, part A, p. 397; (b) G. Casiraghi, F. Zanardi, G. Rassu and P. Spanu, Chem. Rev., 1995, 95, 1677. For recent methods, see (c) A. K. Saksena, R. G. Lovey, V. M. Girigavallabhan and A. K. Ganguly, J. Org. Chem., 1986, 51, 5024; (d) I. Savage and E. J. Thomas, J. Chem. Soc., Chem. Commun., 1989, 717; (e) T. Mukaiyama, K. Suzuki, T. Yamada and F. Tabuga, Tetrahedron, 1990, 46, 265; (f) A. Dondoni, S. Franco, F. L. Merchán, P. Merino and T. Tejero, Tetrahedron Lett., 1993, 34, 5479; (g) R. F. W. Jackson, N. J. Palmer, M. J. Wythes, W. Clegg and M. R. J. Elsegood, J. Org. Chem., 1995, 60, 6431; (h) P. Garner and J. M. Park, J. Org. Chem., 1988, 53, 2979; (i) A. Dureault, F. Carreaux and J. C. Depezay, Synthesis, 1991, 150; (j) M. Irama, H. Hioki and S. Ito, Tetrahedron Lett., 1988, 29, 3125; (k) B. K. Banik, M. S. Manhas and A. K. Bose, J. Org. Chem., 1993, 58, 307; (l) M. M. Paz and F. J. Sardina, J. Org. Chem., 1993, 58, 6990; (m) F. Matsuura, Y. Hamada and T. Shiori, Tetrahedron Lett., 1994, 35, 733; (n) B. M. Trost, A. C. Krueger, R. C. Bunt and J. Zambrano, J. Am. Chem. Soc., 1996, 118, 6520; (o) S. H. Kang and H.-W. Choi, Chem. Commun., 1996, 1521.
15. For reviews, see (a) P. Garner, in Studies in Natural Products Chemistry, ed. Atta-Ur Rahman, Elsevier, Amsterdam, 1988, vol. 1, part A, p. 397; (b) G. Casiraghi, F. Zanardi, G. Rassu and P. Spanu, Chem. Rev., 1995, 95, 1677. For recent methods, see (c) A. K. Saksena, R. G. Lovey, V. M. Girigavallabhan and A. K. Ganguly, J. Org. Chem., 1986, 51, 5024; (d) I. Savage and E. J. Thomas, J. Chem. Soc., Chem. Commun., 1989, 717; (e) T. Mukaiyama, K. Suzuki, T. Yamada and F. Tabuga, Tetrahedron, 1990, 46, 265; (f) A. Dondoni, S. Franco, F. L. Merchán, P. Merino and T. Tejero, Tetrahedron Lett., 1993, 34, 5479; (g) R. F. W. Jackson, N. J. Palmer, M. J. Wythes, W. Clegg and M. R. J. Elsegood, J. Org. Chem., 1995, 60, 6431; (h) P. Garner and J. M. Park, J. Org. Chem., 1988, 53, 2979; (i) A. Dureault, F. Carreaux and J. C. Depezay, Synthesis, 1991, 150; (j) M. Irama, H. Hioki and S. Ito, Tetrahedron Lett., 1988, 29, 3125; (k) B. K. Banik, M. S. Manhas and A. K. Bose, J. Org. Chem., 1993, 58, 307; (l) M. M. Paz and F. J. Sardina, J. Org. Chem., 1993, 58, 6990; (m) F. Matsuura, Y. Hamada and T. Shiori, Tetrahedron Lett., 1994, 35, 733; (n) B. M. Trost, A. C. Krueger, R. C. Bunt and J. Zambrano, J. Am. Chem. Soc., 1996, 118, 6520; (o) S. H. Kang and H.-W. Choi, Chem. Commun., 1996, 1521.
16. For reviews, see (a) P. Garner, in Studies in Natural Products Chemistry, ed. Atta-Ur Rahman, Elsevier, Amsterdam, 1988, vol. 1, part A, p. 397; (b) G. Casiraghi, F. Zanardi, G. Rassu and P. Spanu, Chem. Rev., 1995, 95, 1677. For recent methods, see (c) A. K. Saksena, R. G. Lovey, V. M. Girigavallabhan and A. K. Ganguly, J. Org. Chem., 1986, 51, 5024; (d) I. Savage and E. J. Thomas, J. Chem. Soc., Chem. Commun., 1989, 717; (e) T. Mukaiyama, K. Suzuki, T. Yamada and F. Tabuga, Tetrahedron, 1990, 46, 265; (f) A. Dondoni, S. Franco, F. L. Merchán, P. Merino and T. Tejero, Tetrahedron Lett., 1993, 34, 5479; (g) R. F. W. Jackson, N. J. Palmer, M. J. Wythes, W. Clegg and M. R. J. Elsegood, J. Org. Chem., 1995, 60, 6431; (h) P. Garner and J. M. Park, J. Org. Chem., 1988, 53, 2979; (i) A. Dureault, F. Carreaux and J. C. Depezay, Synthesis, 1991, 150; (j) M. Irama, H. Hioki and S. Ito, Tetrahedron Lett., 1988, 29, 3125; (k) B. K. Banik, M. S. Manhas and A. K. Bose, J. Org. Chem., 1993, 58, 307; (l) M. M. Paz and F. J. Sardina, J. Org. Chem., 1993, 58, 6990; (m) F. Matsuura, Y. Hamada and T. Shiori, Tetrahedron Lett., 1994, 35, 733; (n) B. M. Trost, A. C. Krueger, R. C. Bunt and J. Zambrano, J. Am. Chem. Soc., 1996, 118, 6520; (o) S. H. Kang and H.-W. Choi, Chem. Commun., 1996, 1521.
17. For reviews, see (a) P. Garner, in Studies in Natural Products Chemistry, ed. Atta-Ur Rahman, Elsevier, Amsterdam, 1988, vol. 1, part A, p. 397; (b) G. Casiraghi, F. Zanardi, G. Rassu and P. Spanu, Chem. Rev., 1995, 95, 1677. For recent methods, see (c) A. K. Saksena, R. G. Lovey, V. M. Girigavallabhan and A. K. Ganguly, J. Org. Chem., 1986, 51, 5024; (d) I. Savage and E. J. Thomas, J. Chem. Soc., Chem. Commun., 1989, 717; (e) T. Mukaiyama, K. Suzuki, T. Yamada and F. Tabuga, Tetrahedron, 1990, 46, 265; (f) A. Dondoni, S. Franco, F. L. Merchán, P. Merino and T. Tejero, Tetrahedron Lett., 1993, 34, 5479; (g) R. F. W. Jackson, N. J. Palmer, M. J. Wythes, W. Clegg and M. R. J. Elsegood, J. Org. Chem., 1995, 60, 6431; (h) P. Garner and J. M. Park, J. Org. Chem., 1988, 53, 2979; (i) A. Dureault, F. Carreaux and J. C. Depezay, Synthesis, 1991, 150; (j) M. Irama, H. Hioki and S. Ito, Tetrahedron Lett., 1988, 29, 3125; (k) B. K. Banik, M. S. Manhas and A. K. Bose, J. Org. Chem., 1993, 58, 307; (l) M. M. Paz and F. J. Sardina, J. Org. Chem., 1993, 58, 6990; (m) F. Matsuura, Y. Hamada and T. Shiori, Tetrahedron Lett., 1994, 35, 733; (n) B. M. Trost, A. C. Krueger, R. C. Bunt and J. Zambrano, J. Am. Chem. Soc., 1996, 118, 6520; (o) S. H. Kang and H.-W. Choi, Chem. Commun., 1996, 1521.
18. For reviews, see (a) P. Garner, in Studies in Natural Products Chemistry, ed. Atta-Ur Rahman, Elsevier, Amsterdam, 1988, vol. 1, part A, p. 397; (b) G. Casiraghi, F. Zanardi, G. Rassu and P. Spanu, Chem. Rev., 1995, 95, 1677. For recent methods, see (c) A. K. Saksena, R. G. Lovey, V. M. Girigavallabhan and A. K. Ganguly, J. Org. Chem., 1986, 51, 5024; (d) I. Savage and E. J. Thomas, J. Chem. Soc., Chem. Commun., 1989, 717; (e) T. Mukaiyama, K. Suzuki, T. Yamada and F. Tabuga, Tetrahedron, 1990, 46, 265; (f) A. Dondoni, S. Franco, F. L. Merchán, P. Merino and T. Tejero, Tetrahedron Lett., 1993, 34, 5479; (g) R. F. W. Jackson, N. J. Palmer, M. J. Wythes, W. Clegg and M. R. J. Elsegood, J. Org. Chem., 1995, 60, 6431; (h) P. Garner and J. M. Park, J. Org. Chem., 1988, 53, 2979; (i) A. Dureault, F. Carreaux and J. C. Depezay, Synthesis, 1991, 150; (j) M. Irama, H. Hioki and S. Ito, Tetrahedron Lett., 1988, 29, 3125; (k) B. K. Banik, M. S. Manhas and A. K. Bose, J. Org. Chem., 1993, 58, 307; (l) M. M. Paz and F. J. Sardina, J. Org. Chem., 1993, 58, 6990; (m) F. Matsuura, Y. Hamada and T. Shiori, Tetrahedron Lett., 1994, 35, 733; (n) B. M. Trost, A. C. Krueger, R. C. Bunt and J. Zambrano, J. Am. Chem. Soc., 1996, 118, 6520; (o) S. H. Kang and H.-W. Choi, Chem. Commun., 1996, 1521.
19. For a recent review on the synthesis of complex nucleoside antibiotics, see S. Knapp, Chem. Rev., 1995, 95, 1859. For recent total synthesis of (+)-polyoxin J, see N. Chida, K. Koizumi, Y. Kitida, C. Yokoyama and S. Ogawa, J. Chem. Soc., Chem. Commun., 1994. 111; A. Dondoni, F. Junquera, F. L. Merchán, P. Merino and T. Tejero, J. Chem. Soc., Chem. Commun., 1995, 2127.
20. For a recent review on the synthesis of complex nucleoside antibiotics, see S. Knapp, Chem. Rev., 1995, 95, 1859. For recent total synthesis of (+)-polyoxin J, see N. Chida, K. Koizumi, Y. Kitida, C. Yokoyama and S. Ogawa, J. Chem. Soc., Chem. Commun., 1994. 111; A. Dondoni, F. Junquera, F. L. Merchán, P. Merino and T. Tejero, J. Chem. Soc., Chem. Commun., 1995, 2127.
21. For a recent review on the synthesis of complex nucleoside antibiotics, see S. Knapp, Chem. Rev., 1995, 95, 1859. For recent total synthesis of (+)-polyoxin J, see N. Chida, K. Koizumi, Y. Kitida, C. Yokoyama and S. Ogawa, J. Chem. Soc., Chem. Commun., 1994. 111; A. Dondoni, F. Junquera, F. L. Merchán, P. Merino and T. Tejero, J. Chem. Soc., Chem. Commun., 1995, 2127.
22. For reviews, see G. I. Georg and V. T. Ravikumar, in The Organic Chemistry of β-Lactams, ed. G. I. Georg, VCH, New York, 1993, p. 295; J. Backes, in Houben-Weyl Methoden der Organischen Chemie, ed. E. Muller and O. Bayer, Band E16B, Theime, Stuttgart, 1991, p. 31.
23. For reviews, see G. I. Georg and V. T. Ravikumar, in The Organic Chemistry of β-Lactams, ed. G. I. Georg, VCH, New York, 1993, p. 295; J. Backes, in Houben-Weyl Methoden der Organischen Chemie, ed. E. Muller and O. Bayer, Band E16B, Theime, Stuttgart, 1991, p. 31.
24. C. Palomo, J. M. Aizpurua, C. Cuevas, R. Urchegui and A. Linden, J. Org. Chem., 1996, 61, 4400.
25. For cycloadditions of glyceraldehyde imines, see C. Hubschwerben and G. Schmid, Helv. Chim. Acta, 1983, 66, 2206; D. R. Wagle, G. Garai, J. Chiang, M. S. Manhas and A. K. Bose, J. Org. Chem, 1988, 29, 5065; S. Saito, T. Ishikawa and T. Moriwake, Synlett., 1993, 139.
26. For cycloadditions of glyceraldehyde imines, see C. Hubschwerben and G. Schmid, Helv. Chim. Acta, 1983, 66, 2206; D. R. Wagle, G. Garai, J. Chiang, M. S. Manhas and A. K. Bose, J. Org. Chem, 1988, 29, 5065; S. Saito, T. Ishikawa and T. Moriwake, Synlett., 1993, 139.
27. For cycloadditions of glyceraldehyde imines, see C. Hubschwerben and G. Schmid, Helv. Chim. Acta, 1983, 66, 2206; D. R. Wagle, G. Garai, J. Chiang, M. S. Manhas and A. K. Bose, J. Org. Chem, 1988, 29, 5065; S. Saito, T. Ishikawa and T. Moriwake, Synlett., 1993, 139.
28. C. Palomo, F. P. Cossío, C. Cuevas, B. Lecea, A. Mielgo, P. Román, A. Luque and M. J. Martínez-Ripoll, J. Am. Chem. Soc., 1992, 114, 9360; M. Jayaraman, A. R. A. S. Deshmukh and B. M. Bahawal, J. Org. Chem., 1994, 59, 932.
29. C. Palomo, F. P. Cossío, C. Cuevas, B. Lecea, A. Mielgo, P. Román, A. Luque and M. J. Martínez-Ripoll, J. Am. Chem. Soc., 1992, 114, 9360; M. Jayaraman, A. R. A. S. Deshmukh and B. M. Bahawal, J. Org. Chem., 1994, 59, 932.