Direct synthesis of G-2N

Journal of Organic Chemistry

Volumn 61, Issue 8, 1996, Pages 2770-2773

  Kraus, George A ^a   Zhao, Guohua ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRAQUINONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PHOTOCHEMISTRY; REACTION ANALYSIS;

EID: 0029897253     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9517609     Document Type: Article

References (17)

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2. Bowie, J. H.; Johnson, A. W. Tetrahedron Lett. 1967, 8, 1499.
3. Pradimicins: Tsunakawa, M.; Nishio, M.; Ohkuma, H.; Tsuno, T.; Konishi, M.; Naito, T.; Oki, T.; Kawaguchi, H. J. Org. Chem. 1989, 54, 2532.
4. Isolation and structure determinations of G-2N and G-2A: Gerber. N. N.; Lechevalier, M. P. Can. J. Chem. 1984, 62, 2818. Rickards, R. W. J. Antibiot. 1989, 42, 336. Hauser, F. M.; Caringal, Y. J. Org. Chem. 1990, 55, 555.
5. Isolation and structure determinations of G-2N and G-2A: Gerber. N. N.; Lechevalier, M. P. Can. J. Chem. 1984, 62, 2818. Rickards, R. W. J. Antibiot. 1989, 42, 336. Hauser, F. M.; Caringal, Y. J. Org. Chem. 1990, 55, 555.
6. Isolation and structure determinations of G-2N and G-2A: Gerber. N. N.; Lechevalier, M. P. Can. J. Chem. 1984, 62, 2818. Rickards, R. W. J. Antibiot. 1989, 42, 336. Hauser, F. M.; Caringal, Y. J. Org. Chem. 1990, 55, 555.
7. Kelly, T. R., Xu, W.; Ma, Z.; Li, Q.; Bhushan, V. J. Am Chem. Soc. 1993, 115, 5843.
8. Saba, G.; Lai, A.; Monduzzi, M.; Gelli, G. J. Chem. Soc., Perkin Trans. 2 1983, 1569.
9. Hassall, C.; Morgan, B. A. J. Chem. Soc., Perkin Trans, 1 1973, 2853.
10. Photoenolization review: Sammes, P. G. Tetrahedron 1976, 32, 405, Kraus, G. A.; Wu, Y. J. Org. Chem. 1992, 57, 2922.
11. Photoenolization review: Sammes, P. G. Tetrahedron 1976, 32, 405, Kraus, G. A.; Wu, Y. J. Org. Chem. 1992, 57, 2922.
12. Prepared using acetyl chloride as in ref 6.
13. Savard, J.; Brassard, P. Tetrahedron 1984, 40, 3455.
14. Bhatt, M. V.; Kulkarni, S. U. Synthesis 1983, 249. In our hands, the pyridinium hydrochloride conditions successfully employed by Kelly returned starting material.
15. Brownbridge, P ; Chan, T. H.; Brook, M. A.; Kang, G. J. Can. J Chem. 1983, 61, 688.
16. KS-619-1: Matsuda, Y ; Kase, H. J. Antibiot. 1987, 40, 1104. Yasuzawa, T ; Yoshida, M.; Shirahata, K.; Sano, H. J. Antibiot. 1987, 40, 1111
17. KS-619-1: Matsuda, Y ; Kase, H. J. Antibiot. 1987, 40, 1104. Yasuzawa, T ; Yoshida, M.; Shirahata, K.; Sano, H. J. Antibiot. 1987, 40, 1111