Synthesis of a bicyclic oxamazin. A novel heteroatom activated β-lactam

Tetrahedron

Volumn 52, Issue 12, 1996, Pages 4225-4238

  Ghosh, Manuka ^a   Miller, Marvin J ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM DERIVATIVE; OXAMAZIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL;

EID: 0029866843     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00080-4     Document Type: Article

References (23)

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2. Cohen, N. C. J. Med. Chem. 1983, 26, 259.
3. Zercher, C. K.; Miller, M. J. Tetrahedron Lett. 1989, 30, 7009.
4. Kroenthal, D.; Kuester, P.; Koster, W. H. Abstracts from the Tenth International Congress of Heterocyclic Chemistry, Abstract G3-25, 1985.
5. a) Miller, M. J.; Mattingly, P. G.; Morrison, M. A.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1980, 102, 7026.
6. b) Miller, M. J.; Mattingly, P. G. Tetrahedron 1983, 39, 2563.
7. c) Miller, M. J. Acc. Chem. Res. 1986, 19, 49 and references cited therein.
8. Brooks, D. W.; Lu, L. D. L.; Masamune, S. Angew. Chem., Int. Ed. Engl. 1979, 18, 72.
9. Miller, M. J. J. Org. Chem. 1980, 45, 3131.
10. Fotsch, C. H.; Chamberlin, A. R. J. Org. Chem. 1991, 56, 4141-4147. For a review on macrolide antibiotics synthesis, see: Masamune, S.; McCarthy, P. A. in Macrolide Antibiotics; Omura, S., Ed.; Academic Press; Orlando, 1984; pp 127-198.
11. Fotsch, C. H.; Chamberlin, A. R. J. Org. Chem. 1991, 56, 4141-4147. For a review on macrolide antibiotics synthesis, see: Masamune, S.; McCarthy, P. A. in Macrolide Antibiotics; Omura, S., Ed.; Academic Press; Orlando, 1984; pp 127-198.
12. For reviews, see: Wierenga, W. in The Total Synthesis of Natural Products; ApSimon, J. Ed.; John Wiley and Sons: New York, 1981; pp 287-351. Westly, J. W. in Antibiotics, Chemotherapeutics, and Antibacterial Agents for Disease Control; Grayson, M., Ed.; John Wiley and Sons: New York, 1982; pp 301-318.
13. For reviews, see: Wierenga, W. in The Total Synthesis of Natural Products; ApSimon, J. Ed.; John Wiley and Sons: New York, 1981; pp 287-351. Westly, J. W. in Antibiotics, Chemotherapeutics, and Antibacterial Agents for Disease Control; Grayson, M., Ed.; John Wiley and Sons: New York, 1982; pp 301-318.
14. Mitsunobu, O. Synthesis 1981, 1. Also see: reference 5 (c) for application of this reagent system to β-lactam synthesis.
15. Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190.
16. Jeffrey, P. D.; McCombie, S. W. J. Org. Chem. 1982, 47, 587 and references cited therein.
17. The low yield of the desired product in absence of Pd(0) may signify some involvement of Pd in the cyclization process.
18. a) Hirose, T.; Chiba, K.; Mishio, S.; Nakano, J.; Uno, H. Heterocycles, 1982, 19, 1019.
19. b) Zercher, C. K.; Miller, M. J. Tet. Lett. 1989, 30, 7009.
20. Talshian, D. B.; Fraser-Reid, B. J. Org. Chem. 1984, 49, 518.
21. Nakao, Y. in Recent Advances in the Chemistry of β-Lactam Antibiotics; Bentley, P. H., Southgate, R., Eds.; The Royal Society of Chemistry: London, 1989, pp 119-138.
22. Teng, M.; Miller, M. J. J. Am. Chem. Soc. 1993, 115, 548.
23. Gordon, A. J.; Ford, R. A. The Chemist's Companion - A Handbook of Practical Data, Techniques, and References, John Wiley and Sons: New York, 1972; pp 408-456.