Total Synthesis of TAN-1057 A/B, a New Dipeptide Antibiotic from Flexibacter sp. PK-74

European Journal of Organic Chemistry

Volumn , Issue 5, 1998, Pages 777-783

  Sokolov, Viktor V ^a,c   Kozhushkov, Sergei I ^a   Nikolskaya, Sofia ^a,c   Belov, Vladimir N ^a,c   Es Sayed, Mazen ^b   De Meijere, Armin ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b BAYER AG   (Germany)

^c ST PETERSBURG STATE UNIVERSITY   (Russian Federation)

Author keywords

Antibiotics; Dipeptides; Heterocycles; Amino acid

Indexed keywords

EID: 0001098146     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199805)1998:5<777::AID-EJOC777>3.0.CO;2-W     Document Type: Article

References (20)

1. Y. Funabashi, S. Tsubotani, K. Koyama, N. Katayama, S. Harada, Tetrahedron 1993, 49, 13-28.
2. H. M. M. Bastiaans, A. E. Alewijnse, J. van der Baan, H. C. J. Ottenheijm, Tetrahedron Lett. 1994, 35, 7659-7660.
3. In a report on an efficient method for the preparation of amidinoureas, activities towards the synthesis of TAN-1057A were mentioned. Cf. C. Yuan, R. M. Williams, Tetrahedron Lett. 1996, 37, 1945-1948.
4. The recent report on the completion of a total synthesis of TAN-1057A-D (Cf. C. Yuan, M. Williams, J. Am. Chem Soc 1997, 119, 11777-11784.) prompts us to publish our own apparently superior synthesis before completing any further tests.
5. L. N. Jungheim, S. K. Sigmund, J. Org. Chem. 1987, 52, 4007-4013.
6. P. Quitt, J. Hellerbach, K. Vogler, Helv. Chim. Acta. 1963, 31-32, 327-333.
7. D. H. Rich, J. Tarn, P. Mathiaparam, J. Grant, Synthesis 1975, 402-404. For the NMR data of δ see: Y. Torisawa, M. Nakagawa, T. Hosaka, K. Tanabe, Z. Lai, K. Ogata, T. Nakata, T. Oishi, T. Hino, J. Org. Chem. 1992, 57, 5741-5747.
8. D. H. Rich, J. Tarn, P. Mathiaparam, J. Grant, Synthesis 1975, 402-404. For the NMR data of δ see: Y. Torisawa, M. Nakagawa, T. Hosaka, K. Tanabe, Z. Lai, K. Ogata, T. Nakata, T. Oishi, T. Hino, J. Org. Chem. 1992, 57, 5741-5747.
9. Y. H. Kim, J. Lee, Heterocycles 1983, 20, 1769
10. Y. Liwschitz, Y. Edlitz-Pfeffermann, Y. Lapidoth, J. Am. Chem. Soc. 1956, 78, 3069-3072.
11. M. Waki, Y. Kitajima, N. Izumiya, Synthesis 1981, 266-268.
12. St. Guttmann, R. A. Boissonnas, Helv. Chim. Acta. 1958, 41, 1852.
13. C. Parkanyi, H. L. Yuan, N. S. Cho, J.-H. J. Jaw, T. E. Woodhouse, T. L. Aung, J. Heterocycl. Chem. 1989, 26, 1331-1334.
14. D. L. Klayman, R. J. Shine, J. D. Bower, J. Org. Chem. 1972, 37, 1532-1537.
15. L. A. Reiter, K. E. Brighty, R. A. Bryant, M. E. Goldsmith, Synth. Commun. 1996, 26, 1423-1429.
16. The preparation of 4 has been reported but not its characterization. Cf. R. Polt, L. Szabo, J. Treiberg, Yu. Li, V. Hruby, J. Am. Chem Soc. 1992, 114, 10249-10258.
17. J. Söll, A. Stutzer, Ber. Dtsch. Chem. Ges. 1909, 4532-4541.
18. M. Otsuka, A. Kittaka, T. Iimori, H. Yamashita, S. Kobayashi, M. Ohno, Chem. Pharm. Bull. 1985, 33, 509-514.
19. M. Jetten, C. O. M. Peters, J. W. F. M. van Nispen, H. C. J. Ottenheim, Tetrahedron Lett. 1991, 32, 6025-6028.
20. [4] as an oil without any physical and spectral data.