Total synthesis of diazaquinomycin A

Tetrahedron Letters

Volumn 39, Issue 7, 1998, Pages 673-676

  Pérez, José María ^a   López Alvarado, Pilar ^a   Avendaño, Carmen ^a   Menéndez, J Carlos ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; DIAZAQUINOMYCIN A; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; DRUG SYNTHESIS;

EID: 0032509933     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10589-5     Document Type: Article

References (22)

1. 1 a) Omura, S.; Nakagawa, A.; Aoyama, H.; Hinotozawa, K.; Sano, H., Tetrahedron Lett., 1983, 24, 3643.
2. b) Omura, S., Microbiol. Rev., 1986, 50, 259.
3. 2 a) Omura, S.; Murata, M.; Kimura, K.; Matsakura, S.; Nishihara, T.; Tanaka, H., J. Antibiot., 1985, 38, 1016.
4. b) Murata, M.; Miyasaka, T.; Tanaka, H.; Omura, S., J. Antibiot., 1985, 38, 1025.
5. 3 Krapcho, A. P.; Maresch, M. J.; Hacker, M. P.; Hazelhurst, L.; Menta, E.; Oliva, A.; Spinelli, S.; Beggiolin, G.; Giuliani, F. C.; Pezzoni, G.; Tignella, S. Curr. Med. Chem. 1995, 2, 803.
6. 4 Tsuzuki, K.; Yakozuka, T.; Murata, M.; Tanaka, H.; Omura, S., J. Antibiot., 1989, 42, 727.
7. 5 See, for instance: a) Blanco, M. M.; Avendaño, C.; Menéndez, J. C., Tetrahedron, 1997, 53, 11465 and references therein.
8. b) Avendaño, C.; Menéndez, J. C., Recent Research Developments in Organic Chemistry, in press.
9. 6 Kelly, T. R.; Field, J. A.; Li, Q., Tetrahedron Lett., 1988, 29, 3545.
10. 7 Serckx-Poncin, B.; Hesbain-Frisque, A. M.; Ghosez, L., Tetrahedron Lett., 1982, 23, 3261. For recent reviews on azadienes and hetero Diels-Alder chemistry, see: a) Weinreb, S. M., in Paquette, L. A. (ed.), Comprehensive Organic Synthesis, vol. 5, p. 401 (Trost, B. M., Fleming, I., general editors). Pergamon Press, 1991.
11. 7 Serckx-Poncin, B.; Hesbain-Frisque, A. M.; Ghosez, L., Tetrahedron Lett., 1982, 23, 3261. For recent reviews on azadienes and hetero Diels-Alder chemistry, see: a) Weinreb, S. M., in Paquette, L. A. (ed.), Comprehensive Organic Synthesis, vol. 5, p. 401 (Trost, B. M., Fleming, I., general editors). Pergamon Press, 1991.
12. b) Boger, D. L., in Paquette, L. A. (ed.), Comprehensive Organic Synthesis, vol. 5, p. 451 (Trost, B. M., Fleming, I., general editors). Pergamon Press, 1991.
13. c) Barluenga, J.; Tomás, M., Adv. Heterocycl. Chem., 1993, 57, 1.
14. d) Tietze, L. F.; Kettschau, G., Topics Curr. Chem., 1997, 189, 1.
15. 8 Synthesis of 2-methyl-2-hexenal: Satsumabayashi, S.; Nakajo, K.; Soneda, R.; Motoki, S., Bull. Soc. Chim. Jpn., 1970, 43, 1586. The dimethylhydrazone was prepared using the method described in reference 10a.
16. 9 Perumal, P. T.; Bhatt, M. V., Synthesis, 1979, 205.
17. 10 Acid-promoted elimination: a) Waldner, A. Helv. Chim. Acta 1988, 71, 486.
18. b) Nebois, P.; Barret, R.; Fillion, H. Tetrahedron Lett. 1990, 31, 2569. Thermal elimination: Pérez, J. M.; Avendaño, C.; Menéndez, J. C., Tetrahedron Lett., 1997, 38, 4717.
19. b) Nebois, P.; Barret, R.; Fillion, H. Tetrahedron Lett. 1990, 31, 2569. Thermal elimination: Pérez, J. M.; Avendaño, C.; Menéndez, J. C., Tetrahedron Lett., 1997, 38, 4717.
20. 11 Heaney, H. Aldrichim. Acta, 1993, 26, 35.
21. 12 López-Alvarado, P.; Avendaño, C.; Menéndez, J. C., Synthesis, in press.
22. 13 Pérez, J. M.; López-Alvarado, P.; Alonso, M. A.; Avendaño, C.; Menéndez, J. C., Tetrahedron Lett., 1996, 37, 6955.