Indium and zinc mediated Barbier type reactions: Allylation and propargylation reactions of 6-oxopenicillanate and 7-oxocephalosporanate

Tetrahedron Letters

Volumn 40, Issue 9, 1999, Pages 1725-1728

  Cho, Yong Seo ^a   Lee, Jie Eun ^a   Pae, Ae Nim ^a   Choi, Kyung Il ^a   Koh, Hun Yeong ^a  

^a Korea Institute of Science and Technology   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

6 EXOMETHYLENEPENAM; 6 OXOPENICILLINATE; 7 OXOCEPHALOSPORANATE; BETA LACTAM ANTIBIOTIC; BETA LACTAMASE INHIBITOR; CEPHALOSPORIN DERIVATIVE; INDIUM; PENICILLIN DERIVATIVE; UNCLASSIFIED DRUG; ZINC;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; REACTION TIME; STEREOSPECIFICITY; SYNTHESIS;

EID: 0033605177     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00037-4     Document Type: Article

References (13)

1. 1. S. Adam, Heterocycles, 1984, 22, 1509; Y. L. Chen, C-W. Chang, K. Hedberg, K. Guarino, W. D. Welch, L. Kiessling, J. A. Retsema, S. L. Haskell, M. Andersen, M. Manousos and J. F. Barret, J. Antibiotics, 1987, XL, 803; S. Adam, R. Then and P. Angehrn, J. Antibiotics, 1992, 45. 587.
2. 1. S. Adam, Heterocycles, 1984, 22, 1509; Y. L. Chen, C-W. Chang, K. Hedberg, K. Guarino, W. D. Welch, L. Kiessling, J. A. Retsema, S. L. Haskell, M. Andersen, M. Manousos and J. F. Barret, J. Antibiotics, 1987, XL, 803; S. Adam, R. Then and P. Angehrn, J. Antibiotics, 1992, 45. 587.
3. 1. S. Adam, Heterocycles, 1984, 22, 1509; Y. L. Chen, C-W. Chang, K. Hedberg, K. Guarino, W. D. Welch, L. Kiessling, J. A. Retsema, S. L. Haskell, M. Andersen, M. Manousos and J. F. Barret, J. Antibiotics, 1987, XL, 803; S. Adam, R. Then and P. Angehrn, J. Antibiotics, 1992, 45. 587.
4. 2. Y. L. Chen, C-W. Chang and K. Hedberg, Tetrahedron Lett., 1986, 27, 3449.
5. 3. L. A. Reed III, D. A. Charieson and R. A. Volkmann, Tetrahedron Lett., 1987, 28, 3431 ; C. Im, S. N. Maiti, R. G. Micetich, M. Daneshtalab, K. Atchison, O. A. Phillips and C. Kunugita, J. Antibiotics, 1994, 47. 1030.
6. 3. L. A. Reed III, D. A. Charieson and R. A. Volkmann, Tetrahedron Lett., 1987, 28, 3431 ; C. Im, S. N. Maiti, R. G. Micetich, M. Daneshtalab, K. Atchison, O. A. Phillips and C. Kunugita, J. Antibiotics, 1994, 47. 1030.
7. 4. M. Jayaraman, M. S. Manhas and A. K. Bose, Tetrahedron Lett., 1997, 38, 709.
8. 5. J. D. Buynak, A. S. Rao and S. D. Nidamarthy, Tetrahedron Lett., 1998, 39, 4945.
9. 6. J. D. Buynak, H. B. Borate, G. W. Lamb, D. D. Khasnis, C. Husting, H. Isom and U. Siriwardane, J. Org. Chem. 1993, 58, 1325; J. D. Buynak, D. Khasnis, B. Bachmann, K. Wu and G. Lamb, J. Am. Chem. Soc. 1994, 116, 10955.
10. 6. J. D. Buynak, H. B. Borate, G. W. Lamb, D. D. Khasnis, C. Husting, H. Isom and U. Siriwardane, J. Org. Chem. 1993, 58, 1325; J. D. Buynak, D. Khasnis, B. Bachmann, K. Wu and G. Lamb, J. Am. Chem. Soc. 1994, 116, 10955.
11. 3, δ ): 171.0, 168.2, 161.1, 139.8, 139.6, 130.9, 129.2, 129.1, 129.0, 128.9, 128.7, 128.6, 128.5, 128.2, 127.9, 127.7, 127.4, 126.0, 121.0, 87.3, 80.2, 63.4, 62.4, 39.7, 26.8, 21.1.
12. 8. M. B. Isaac, and T. -H. Chan, Tetrahedron Lett., 1995, 36, 8957; S. -C. H. Diana, K. -Y. Sim and T. -P. Loh, Synlett 1996, 263.
13. 8. M. B. Isaac, and T. -H. Chan, Tetrahedron Lett., 1995, 36, 8957; S. -C. H. Diana, K. -Y. Sim and T. -P. Loh, Synlett 1996, 263.