Diastereoselective synthesis of α-butadienyl-β-lactams and some stereochemical aspects of their Diels-Alder adducts

Heterocycles

Volumn 52, Issue 2, 2000, Pages 603-619

  Sharma, Arun K ^a   Kumar, R Senthil ^a   Mahajan, Mohinder P ^a  

^a GURU NANAK DEV UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID ETHYL ESTER; BETA LACTAM DERIVATIVE; FUMARIC ACID DERIVATIVE; MALEIMIDE DERIVATIVE; TRIAZOLINE DERIVATIVE;

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

EID: 0034143243     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-99-s45     Document Type: Article

References (37)

1. J. Howie, Br. Med. J., 1986, 293, 158; C. Fletcher, Br. Med. J., 1990, 300, 1289;
2. J. Howie, Br. Med. J., 1986, 293, 158; C. Fletcher, Br. Med. J., 1990, 300, 1289;
3. For reviews on β-lactam antibiotics, see: C. Palomo In Recent Progress in the Chemical Synthesis of Antibiotics, ed. by G. Lukacs, and M. Ohno, Springer-Verlag , Berlin-Heidelberg, 1990, pp. 565-612; R. Southgate and S. Elson In Progress in the Chemistry of Organic Natural Products; ed. by W. Herz, H. Grisebach, G. W. Kirby, and Ch. Tamm, Springer-Verlag , New York, 1985, Vol. 47, pp. 1-106; W. Durckheimer, J. Blumbach, R. Lattrell, and K. H. Sheunemann, Angew. Chem., Int. Ed. Engl., 1985, 24, 180; G. A. Koppel In Small Ring Heterocycles; ed. by. A. Hassner, John Wiley, New York, 1983, Part 2, pp. 248-301; A. G. Brown, Pure Appl. Chemistry , 1987, 59, 475; W. Durckheimer, G. Fischer, and R. Lattrell In Recent Advances in the Chemistry of β-Lactam Antibiotics; ed. by P. H. Bentley and R. Southgate, RSC, Cambridge, 1989, p. 49; S. W. Elson In Recent Advances in the Chemistry of β-Lactam Antibiotics; ed. by. P. H. Bentley and R. Southgate, RSC, London, 1989, p. 303.
4. For reviews on β-lactam antibiotics, see: C. Palomo In Recent Progress in the Chemical Synthesis of Antibiotics, ed. by G. Lukacs, and M. Ohno, Springer-Verlag , Berlin-Heidelberg, 1990, pp. 565-612; R. Southgate and S. Elson In Progress in the Chemistry of Organic Natural Products; ed. by W. Herz, H. Grisebach, G. W. Kirby, and Ch. Tamm, Springer-Verlag , New York, 1985, Vol. 47, pp. 1-106; W. Durckheimer, J. Blumbach, R. Lattrell, and K. H. Sheunemann, Angew. Chem., Int. Ed. Engl., 1985, 24, 180; G. A. Koppel In Small Ring Heterocycles; ed. by. A. Hassner, John Wiley, New York, 1983, Part 2, pp. 248-301; A. G. Brown, Pure Appl. Chemistry , 1987, 59, 475; W. Durckheimer, G. Fischer, and R. Lattrell In Recent Advances in the Chemistry of β-Lactam Antibiotics; ed. by P. H. Bentley and R. Southgate, RSC, Cambridge, 1989, p. 49; S. W. Elson In Recent Advances in the Chemistry of β-Lactam Antibiotics; ed. by. P. H. Bentley and R. Southgate, RSC, London, 1989, p. 303.
5. For reviews on β-lactam antibiotics, see: C. Palomo In Recent Progress in the Chemical Synthesis of Antibiotics, ed. by G. Lukacs, and M. Ohno, Springer-Verlag , Berlin-Heidelberg, 1990, pp. 565-612; R. Southgate and S. Elson In Progress in the Chemistry of Organic Natural Products; ed. by W. Herz, H. Grisebach, G. W. Kirby, and Ch. Tamm, Springer-Verlag , New York, 1985, Vol. 47, pp. 1-106; W. Durckheimer, J. Blumbach, R. Lattrell, and K. H. Sheunemann, Angew. Chem., Int. Ed. Engl., 1985, 24, 180; G. A. Koppel In Small Ring Heterocycles; ed. by. A. Hassner, John Wiley, New York, 1983, Part 2, pp. 248-301; A. G. Brown, Pure Appl. Chemistry , 1987, 59, 475; W. Durckheimer, G. Fischer, and R. Lattrell In Recent Advances in the Chemistry of β-Lactam Antibiotics; ed. by P. H. Bentley and R. Southgate, RSC, Cambridge, 1989, p. 49; S. W. Elson In Recent Advances in the Chemistry of β-Lactam Antibiotics; ed. by. P. H. Bentley and R. Southgate, RSC, London, 1989, p. 303.
6. For reviews on β-lactam antibiotics, see: C. Palomo In Recent Progress in the Chemical Synthesis of Antibiotics, ed. by G. Lukacs, and M. Ohno, Springer-Verlag , Berlin-Heidelberg, 1990, pp. 565-612; R. Southgate and S. Elson In Progress in the Chemistry of Organic Natural Products; ed. by W. Herz, H. Grisebach, G. W. Kirby, and Ch. Tamm, Springer-Verlag , New York, 1985, Vol. 47, pp. 1-106; W. Durckheimer, J. Blumbach, R. Lattrell, and K. H. Sheunemann, Angew. Chem., Int. Ed. Engl., 1985, 24, 180; G. A. Koppel In Small Ring Heterocycles; ed. by. A. Hassner, John Wiley, New York, 1983, Part 2, pp. 248-301; A. G. Brown, Pure Appl. Chemistry , 1987, 59, 475; W. Durckheimer, G. Fischer, and R. Lattrell In Recent Advances in the Chemistry of β-Lactam Antibiotics; ed. by P. H. Bentley and R. Southgate, RSC, Cambridge, 1989, p. 49; S. W. Elson In Recent Advances in the Chemistry of β-Lactam Antibiotics; ed. by. P. H. Bentley and R. Southgate, RSC, London, 1989, p. 303.
7. For reviews on β-lactam antibiotics, see: C. Palomo In Recent Progress in the Chemical Synthesis of Antibiotics, ed. by G. Lukacs, and M. Ohno, Springer-Verlag , Berlin-Heidelberg, 1990, pp. 565-612; R. Southgate and S. Elson In Progress in the Chemistry of Organic Natural Products; ed. by W. Herz, H. Grisebach, G. W. Kirby, and Ch. Tamm, Springer-Verlag , New York, 1985, Vol. 47, pp. 1-106; W. Durckheimer, J. Blumbach, R. Lattrell, and K. H. Sheunemann, Angew. Chem., Int. Ed. Engl., 1985, 24, 180; G. A. Koppel In Small Ring Heterocycles; ed. by. A. Hassner, John Wiley, New York, 1983, Part 2, pp. 248-301; A. G. Brown, Pure Appl. Chemistry , 1987, 59, 475; W. Durckheimer, G. Fischer, and R. Lattrell In Recent Advances in the Chemistry of β-Lactam Antibiotics; ed. by P. H. Bentley and R. Southgate, RSC, Cambridge, 1989, p. 49; S. W. Elson In Recent Advances in the Chemistry of β-Lactam Antibiotics; ed. by. P. H. Bentley and R. Southgate, RSC, London, 1989, p. 303.
8. For reviews on β-lactam antibiotics, see: C. Palomo In Recent Progress in the Chemical Synthesis of Antibiotics, ed. by G. Lukacs, and M. Ohno, Springer-Verlag , Berlin-Heidelberg, 1990, pp. 565-612; R. Southgate and S. Elson In Progress in the Chemistry of Organic Natural Products; ed. by W. Herz, H. Grisebach, G. W. Kirby, and Ch. Tamm, Springer-Verlag , New York, 1985, Vol. 47, pp. 1-106; W. Durckheimer, J. Blumbach, R. Lattrell, and K. H. Sheunemann, Angew. Chem., Int. Ed. Engl., 1985, 24, 180; G. A. Koppel In Small Ring Heterocycles; ed. by. A. Hassner, John Wiley, New York, 1983, Part 2, pp. 248-301; A. G. Brown, Pure Appl. Chemistry , 1987, 59, 475; W. Durckheimer, G. Fischer, and R. Lattrell In Recent Advances in the Chemistry of β-Lactam Antibiotics; ed. by P. H. Bentley and R. Southgate, RSC, Cambridge, 1989, p. 49; S. W. Elson In Recent Advances in the Chemistry of β-Lactam Antibiotics; ed. by. P. H. Bentley and R. Southgate, RSC, London, 1989, p. 303.
9. For reviews on β-lactam antibiotics, see: C. Palomo In Recent Progress in the Chemical Synthesis of Antibiotics, ed. by G. Lukacs, and M. Ohno, Springer-Verlag , Berlin-Heidelberg, 1990, pp. 565-612; R. Southgate and S. Elson In Progress in the Chemistry of Organic Natural Products; ed. by W. Herz, H. Grisebach, G. W. Kirby, and Ch. Tamm, Springer-Verlag , New York, 1985, Vol. 47, pp. 1-106; W. Durckheimer, J. Blumbach, R. Lattrell, and K. H. Sheunemann, Angew. Chem., Int. Ed. Engl., 1985, 24, 180; G. A. Koppel In Small Ring Heterocycles; ed. by. A. Hassner, John Wiley, New York, 1983, Part 2, pp. 248-301; A. G. Brown, Pure Appl. Chemistry , 1987, 59, 475; W. Durckheimer, G. Fischer, and R. Lattrell In Recent Advances in the Chemistry of β-Lactam Antibiotics; ed. by P. H. Bentley and R. Southgate, RSC, Cambridge, 1989, p. 49; S. W. Elson In Recent Advances in the Chemistry of β-Lactam Antibiotics; ed. by. P. H. Bentley and R. Southgate, RSC, London, 1989, p. 303.
10. A. Perboni, B. Tamburini, T. Rossi, D. Donati, G. Tarzia, and G. Gaviraghi In Recent Advances in the Chemistry of Anti-Infective Agents; ed. by P. H. Bentley and R. Ponsford, RSC, Cambridge, 1993, p. 21; M. J. Miller, Acc. Chem. Res., 1986, 19, 49.
11. A. Perboni, B. Tamburini, T. Rossi, D. Donati, G. Tarzia, and G. Gaviraghi In Recent Advances in the Chemistry of Anti-Infective Agents; ed. by P. H. Bentley and R. Ponsford, RSC, Cambridge, 1993, p. 21; M. J. Miller, Acc. Chem. Res., 1986, 19, 49.
12. H. E. Imanaka, J. Antibiotics., 1976, 29, 492.
13. H. Akoi, H. Sakai, M. Kohsaka, T. Konomi, J. Hosoda, I. Y. Kobochi, and M. J. Miller, J. Org. Chem., 1994, 59, 4862 and references cited therein. X-F. Ren and E. Turos, J. Org. Chem., 1994, 59, 5858.
14. H. Akoi, H. Sakai, M. Kohsaka, T. Konomi, J. Hosoda, I. Y. Kobochi, and M. J. Miller, J. Org. Chem., 1994, 59, 4862 and references cited therein. X-F. Ren and E. Turos, J. Org. Chem., 1994, 59, 5858.
15. A. Imada, K. Kitano, K. Kintaka, M. Muroi, and M. Asai, Nature , 1981, 289, 590.
16. R. B. Sykes, C. M. Cimarusti, D. P. Bonner, K. Bush, D. M. Floyd, N. H. Georgopapadakou, W. H. Koster, W. C. Liu, W. L. Parker, P. A. Principe, M. L. Rathnum, W. A. Slusarchyk, W. H. Trejo, and J. S. Wells, Nature, 1981, 291, 489.
17. M. I. Page, Acc. Chem. Res., 1984, 17, 144.
18. D. A. Burnett, M. A. Caplen, H. R. Davis, Jr., R. E. Burner, and J. W. Clader, J. Med. Chem., 1994, 37, 1733; J. W. Clader, D. A. Burnett, M. A. Caplen, M. S. Domalski, S. Dugar, W. Vaccaro, R. Sher, M. E. Browne, H. Zhao, R. E. Burrier, B. Salisbury, and H. R. Davis, Jr., J. Med. Chem., 1996, 39, 3684.
19. D. A. Burnett, M. A. Caplen, H. R. Davis, Jr., R. E. Burner, and J. W. Clader, J. Med. Chem., 1994, 37, 1733; J. W. Clader, D. A. Burnett, M. A. Caplen, M. S. Domalski, S. Dugar, W. Vaccaro, R. Sher, M. E. Browne, H. Zhao, R. E. Burrier, B. Salisbury, and H. R. Davis, Jr., J. Med. Chem., 1996, 39, 3684.
20. For review on synthetic aspects of monocyclic β-lactams, see: R. C. Thomas In Recent Progress in the Chemical Synthesis of Antibiotics; ed. by G. Lukacs and M. Ohno, Springer-Verlag, Berlin-Heidelberg, 1990, pp. 533-564.
21. H. Staudinger, Liebigs Ann. Chem., 1907, 356, 51.
22. G. I. Georg, The Organic Chemistry of β-Lactams; VCH, New York, 1992, Chapter 6 and the references cited therein; G. I. Georg and V. T. Ravikumar In The Organic Chemistry of β-Lactams; ed by G. I. Georg, VCH, New York, 1992, p. 295; A. K. Bose, B. K. Banik, and M. S. Manhas, Tetrahedron Lett., 1995, 36, 213; C. Palomo, J. M. Aizpurua, A. Mielgo, and A. Linden, J. Org. Chem., 1996, 61, 9186.
23. G. I. Georg, The Organic Chemistry of β-Lactams; VCH, New York, 1992, Chapter 6 and the references cited therein; G. I. Georg and V. T. Ravikumar In The Organic Chemistry of β-Lactams; ed by G. I. Georg, VCH, New York, 1992, p. 295; A. K. Bose, B. K. Banik, and M. S. Manhas, Tetrahedron Lett., 1995, 36, 213; C. Palomo, J. M. Aizpurua, A. Mielgo, and A. Linden, J. Org. Chem., 1996, 61, 9186.
24. G. I. Georg, The Organic Chemistry of β-Lactams; VCH, New York, 1992, Chapter 6 and the references cited therein; G. I. Georg and V. T. Ravikumar In The Organic Chemistry of β-Lactams; ed by G. I. Georg, VCH, New York, 1992, p. 295; A. K. Bose, B. K. Banik, and M. S. Manhas, Tetrahedron Lett., 1995, 36, 213; C. Palomo, J. M. Aizpurua, A. Mielgo, and A. Linden, J. Org. Chem., 1996, 61, 9186.
25. G. I. Georg, The Organic Chemistry of β-Lactams; VCH, New York, 1992, Chapter 6 and the references cited therein; G. I. Georg and V. T. Ravikumar In The Organic Chemistry of β-Lactams; ed by G. I. Georg, VCH, New York, 1992, p. 295; A. K. Bose, B. K. Banik, and M. S. Manhas, Tetrahedron Lett., 1995, 36, 213; C. Palomo, J. M. Aizpurua, A. Mielgo, and A. Linden, J. Org. Chem., 1996, 61, 9186.
26. A. K. Sharma, S. N. Mazumdar, and M. P. Mahajan, J. Org. Chem., 1996, 61, 5506.
27. A. Gurski and L. S. Liebeskind, J. Am. Chem. Soc., 1993, 115, 6101; A. G. Birchler, F. Liu, and L. S. Liebeskind, J. Org. Chem., 1994, 59, 7737; L. Sun and L. S. Liebeskind, J. Org.Chem., 1995, 60, 8194; M. Taing and H. W. Moore, J. Org. Chem., 1996, 61, 329.
28. A. Gurski and L. S. Liebeskind, J. Am. Chem. Soc., 1993, 115, 6101; A. G. Birchler, F. Liu, and L. S. Liebeskind, J. Org. Chem., 1994, 59, 7737; L. Sun and L. S. Liebeskind, J. Org.Chem., 1995, 60, 8194; M. Taing and H. W. Moore, J. Org. Chem., 1996, 61, 329.
29. A. Gurski and L. S. Liebeskind, J. Am. Chem. Soc., 1993, 115, 6101; A. G. Birchler, F. Liu, and L. S. Liebeskind, J. Org. Chem., 1994, 59, 7737; L. Sun and L. S. Liebeskind, J. Org.Chem., 1995, 60, 8194; M. Taing and H. W. Moore, J. Org. Chem., 1996, 61, 329.
30. A. Gurski and L. S. Liebeskind, J. Am. Chem. Soc., 1993, 115, 6101; A. G. Birchler, F. Liu, and L. S. Liebeskind, J. Org. Chem., 1994, 59, 7737; L. Sun and L. S. Liebeskind, J. Org.Chem., 1995, 60, 8194; M. Taing and H. W. Moore, J. Org. Chem., 1996, 61, 329.
31. 9
32. The assignment of the cis stereochemistry to the β-lactam (5a) and (5b) was based on the observed coupling constant of about 5.6 Hz for methine protons H-3 and H-4.
33. R. Zamboni and G. Just, Can. J. Chem., 1979, 57, 1945; A. G. Bose, G. Spiegelman, and M. S. Manhas, Tetrahedron Lett., 1971, 3167; M. S. Manhas, M. Ghosh, and A. K. Bose, J. Org. Chem., 1990, 55, 575.
34. R. Zamboni and G. Just, Can. J. Chem., 1979, 57, 1945; A. G. Bose, G. Spiegelman, and M. S. Manhas, Tetrahedron Lett., 1971, 3167; M. S. Manhas, M. Ghosh, and A. K. Bose, J. Org. Chem., 1990, 55, 575.
35. R. Zamboni and G. Just, Can. J. Chem., 1979, 57, 1945; A. G. Bose, G. Spiegelman, and M. S. Manhas, Tetrahedron Lett., 1971, 3167; M. S. Manhas, M. Ghosh, and A. K. Bose, J. Org. Chem., 1990, 55, 575.
36. E. L. Clennan and A. D. Earlywine, J. Am. Chem. Soc., 1987, 109, 7104; F. Jensen and C. S. Foote, J. Am. Chem. Soc., 1987, 109, 6376.
37. E. L. Clennan and A. D. Earlywine, J. Am. Chem. Soc., 1987, 109, 7104; F. Jensen and C. S. Foote, J. Am. Chem. Soc., 1987, 109, 6376.