Versatile β-Lactam Synthons: Enantiospecific Synthesis of (−)-Polyoxamic Acid

Journal of Organic Chemistry

Volumn 58, Issue 2, 1993, Pages 307-309

  Banik, Bimal K ^a   Manhas, Maghar S ^a   Bose, Ajay K ^a  

^a STEVENS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33751385575     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00054a007     Document Type: Article

References (27)

1. Studies on Lactams 89. For part 88, see: Banik, B. K.; Manhas, M. S.; Kaluza, Z.; Barakat, K. J.; Bose, A. K. Tetrahedron Lett. 1992, 33, 3603. For part 87, see ref 2. Presented at the 204th National meeting of the American Chemical Society, Washington, D.C., Aug 1992; ORGN 437.
2. Bose, A. K.; Manhas, M. S.; van der Veen, J. M.; Bari, S. S.; Wagle, D. R. Tetrahedron 1992, 48, 4831.
3. Wagle, D. R.; Garai, C.; Chiang, J.; Montelone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hegde, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227.
4. Garai, C. Ph.D. thesis, Stevens Institute of Technology, Hoboken, 1991.
5. Manhas, M. S.; Hegde, V. R.; Wagle, D. R.; Bose, A. K. J. Chem. Soc., Perkin Trans. 1 1985, 2045.
6. Also see: (a) Sheehan, J. C.; Lo, Y. S.; Loliger, J.; Podowell, C. C. J. Org. Chem. 1974, 39, 1444.
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8. Palomo, C.; Cossio, F. P.; Ontoria, J. M.; Odoriozola, J. M. Tetrahedron Lett. 1991, 32, 3105.
9. Isono, K.; Asahi, K.; Suzuki, S. J. Am. Chem. Soc. 1969, 91, 7499.
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11. Ojima, I.; Qiu, X. J. Am. Chem. Soc. 1987, 109, 6537.
12. For synthesis of polyoxamic acid (2) see: (a) Savage, I.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1989, 717.
13. Hirama, M.; Hioki, H.; Ito, S. Tetrahedron Lett. 1988, 29, 3125.
14. Garner, P.; Park, J. M. J. Org. Chem. 1988, 53, 2979.
15. Saksena, A. K.; Lovey, R. G.; Girijavallabhan, V. M.; Ganguly, A. K. J. Org. Chem. 1986, 51, 5024.
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17. Kuzuhara, H.; Emoto, S. Tetrahedron Lett. 1973, 5051.
18. The enantiospecific synthesis of α-azido and α-amino β-lactam from Schiff bases derived from chiral aldehydes and achiral amines was developed independently by two laboratories: (a) Hubschwerlen, C.; Schmidt, G. Helv. Chim. Acta 1983, 66, 2206.
19. Bose, A. K.; Manhas, M. S.; van der Veen, J. M.; Bari, S. S.; Wagle, D. R.; Hegde, V. R. Third International Symposium on Recent Advances in the Chemistry of β-lactam antibiotics, July 1984, spec. publ. No. 52; The Royal Society of Chemistry: London, 1985; p. 387.
20. Bose, A. K.; Manhas, M. S.; van der Veen, J. M.; Bari, S. S.; Wagle, D. R.; Hegde, V. R.; Krishnan, L. Tetrahedron Lett. 1985, 26, 33 and later publications.
21. Bose, A. K.; Womelsdorf, J. F.; Krishnan, L.; Urbanczyk-Lipkowska, Z.; Shelly, D. C.; Manhas, M. S. Tetrahedron 1991, 47, 5379.
22. Bose, A. K.; Hegde, V. R.; Wagle, D. R.; Bari, S. S.; Manhas, M. S. J. Chem. Soc., Chem. Commun. 1986, 161. Also see ref 12b and 12c.
23. Bose, A. K.; Manhas, M. S.; Ghosh, M.; Raju, V. S.; Tabei, K.; Urbanczyk-Lipkowska, Z. Heterocycles 1990, 30, 741.
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25. Huber, R.; Vasella, A. Tetrahedron 1990, 46, 33.
26. Ram, S.; Ehrenkaufer, R. E. Synthesis 1988, 91 and references cited therein.
27. Bose, A. K.; Manhas, M. S.; Ghosh, M.; Shah, M.; Raju, V. S.; Bari, S. S.; Newaz, S. N.; Banik, B. K.; Cnaudhary, A. G.; Barakat, K. J. J. Org. Chem. 1991, 56, 6968.