Concise synthesis of the naphthoate component of N1999-A2

Synlett

Volumn , Issue 1, 1999, Pages 71-72

  Takahashi, K ^a   Hagiwara, M ^a   Ashizawa, S ^a   Hirama, M ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Chlorination; Metalation; N1999 A2; Naphthoate; Neocarzinostatin

Indexed keywords

ANTINEOPLASTIC ANTIBIOTIC; NAPHTHOL DERIVATIVE; ZINOSTATIN;

ARTICLE; BROMINATION; CANCER CELL; CHLORINATION; CHROMATOPHORE; CYTOTOXICITY; DRUG SYNTHESIS; HYDROLYSIS; STRUCTURE ANALYSIS;

EID: 0032934384     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2563     Document Type: Article

References (18)

1. Ando, T.; Ishii, M.; Kajiura, T.; Kameyama, T.; Miwa, K.; Sugiura, Y. Tetrahedron Lett. 1998, 39, 6495.
2. Ishida, N.; Miyazaki, K.; Kumagai, K.; Rikimaru, M. J. Antibiot. 1965, 18, 68; Edo, K.; Mizugaki, M.; Koide, Y.; Seto, H.; Furihata, K.; Otake, N. Ishida, N. Tetrahedron Lett. 1985, 26, 331; Myers, A. G.; Proteau, P. J.; Handel, T. M. J. Am. Chem. Soc. 1988, 110, 7212.
3. Ishida, N.; Miyazaki, K.; Kumagai, K.; Rikimaru, M. J. Antibiot. 1965, 18, 68; Edo, K.; Mizugaki, M.; Koide, Y.; Seto, H.; Furihata, K.; Otake, N. Ishida, N. Tetrahedron Lett. 1985, 26, 331; Myers, A. G.; Proteau, P. J.; Handel, T. M. J. Am. Chem. Soc. 1988, 110, 7212.
4. Ishida, N.; Miyazaki, K.; Kumagai, K.; Rikimaru, M. J. Antibiot. 1965, 18, 68; Edo, K.; Mizugaki, M.; Koide, Y.; Seto, H.; Furihata, K.; Otake, N. Ishida, N. Tetrahedron Lett. 1985, 26, 331; Myers, A. G.; Proteau, P. J.; Handel, T. M. J. Am. Chem. Soc. 1988, 110, 7212.
5. Shibuya, M.; Toyooka, K.; Kubota, S. Tetrahedron Lett. 1984, 25, 1171.
6. Takahashi, K.; Suzuki, T.; Hirama, M. Tetrahedron Lett. 1992, 33, 4603; Takahashi, K.; Tanaka, T.; Suzuki, T.; Hirama, M. Tetrahedron 1994, 50, 1327.
7. Takahashi, K.; Suzuki, T.; Hirama, M. Tetrahedron Lett. 1992, 33, 4603; Takahashi, K.; Tanaka, T.; Suzuki, T.; Hirama, M. Tetrahedron 1994, 50, 1327.
8. For other syntheses, see: Shishido, K.; Yamashita, A.; Hiroya, K.; Fukumoto, K.; Kametani, T. Tetrahedron 1989, 45, 5791; Myers, A. G.; Subramanian, V.; Hammond, M. Tetrahedron Lett. 1996, 37, 587; Rucker, M.; Bruckner, R. Synlett 1997, 1187.
9. For other syntheses, see: Shishido, K.; Yamashita, A.; Hiroya, K.; Fukumoto, K.; Kametani, T. Tetrahedron 1989, 45, 5791; Myers, A. G.; Subramanian, V.; Hammond, M. Tetrahedron Lett. 1996, 37, 587; Rucker, M.; Bruckner, R. Synlett 1997, 1187.
10. For other syntheses, see: Shishido, K.; Yamashita, A.; Hiroya, K.; Fukumoto, K.; Kametani, T. Tetrahedron 1989, 45, 5791; Myers, A. G.; Subramanian, V.; Hammond, M. Tetrahedron Lett. 1996, 37, 587; Rucker, M.; Bruckner, R. Synlett 1997, 1187.
11. Holcombe, J. L.; Livinghouse, T. J. Org. Chem. 1986, 51, 111.
12. Cort, A. D.; Mandolini, L.; Panaioli, S. Synth. Commun. 1988, 18, 613; Baciocchi, E.; Rol, C.; Sebastiani, G. V.; Serena, B. Tetrahedron Lett. 1984, 25, 1945; Dinctürk, S.; Ridd, J. H. J. Chem. Soc. Perkin Trans. II, 1982, 965.
13. Cort, A. D.; Mandolini, L.; Panaioli, S. Synth. Commun. 1988, 18, 613; Baciocchi, E.; Rol, C.; Sebastiani, G. V.; Serena, B. Tetrahedron Lett. 1984, 25, 1945; Dinctürk, S.; Ridd, J. H. J. Chem. Soc. Perkin Trans. II, 1982, 965.
14. Cort, A. D.; Mandolini, L.; Panaioli, S. Synth. Commun. 1988, 18, 613; Baciocchi, E.; Rol, C.; Sebastiani, G. V.; Serena, B. Tetrahedron Lett. 1984, 25, 1945; Dinctürk, S.; Ridd, J. H. J. Chem. Soc. Perkin Trans. II, 1982, 965.
15. Winkle, M. R.; Ronald, R. C. J. Org. Chem. 1982, 47, 2101; Snieckus, V. Chem. Rev. 1990, 90, 879.
16. Winkle, M. R.; Ronald, R. C. J. Org. Chem. 1982, 47, 2101; Snieckus, V. Chem. Rev. 1990, 90, 879.
17. Mortier, J.; Moyroud, J.; Bennetau, B.; Cain, P. A. J. Org. Chem. 1994, 59, 4042.
18. 5 (M+): 296.0452; Found: 296.0449.