Short and efficient enantioselective total synthesis of angucyclinone type antibiotics (+)-rubiginone B2 and (+)-ochromycinone

Chemical Communications

Volumn , Issue 9, 1999, Pages 817-818

  Carreño, M Carmen ^a   Urbano, Antonio ^a   Di Vitta, Claudio ^a,b  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; ALKADIENE; ANTIBIOTIC AGENT; CYCLOHEXANE DERIVATIVE; SULFOXIDE;

AROMATIZATION; ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; ENANTIOMER;

EID: 0033532097     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (24)

1. J. H. Bowie and A. W. Johnson, Tetrahedron Lett., 1967, 1449.
2. M. Oka, H. Kamei, Y. Hamagishi, K. Tomita, T. Miyaki, M. Konishi and T. Oki, J. Antibiot., 1990, 43, 967.
3. R. H. Thomson, in Naturally Occurring Quinones IV, 4th edn., Blackie Academic & Professional, London, 1996;
4. J. Rohr and R. Thiericke, Nat. Prod. Rep., 1992, 9, 103;
5. M. Ogasawara, M. Hasegawa, Y. Hamagishi, H. Kamei and T. Oki, J. Antibiot., 1992, 45, 129.
6. S. J. Gould, X. C. Cheng and C. Melville, J. Am. Chem. Soc., 1994, 116, 1800 and refs. cited therein.
7. K. Krohn and J. Rohr, Top. Curr. Chem., 1997, 188, 128.
8. For other recent references, see: D. S. Larsen and M. D. O'Shea, J. Org. Chem., 1996, 61, 5681;
9. K. Krohn, N. Böker, U. Flörke and C. Freund, J. Org. Chem., 1997, 62, 2350.
10. K. Kim and G. Sulikowski, Angew. Chem., Int. Ed. Engl., 1995, 34, 2396;
11. V. A. Boyd and G. Sulikowski, J. Am. Chem. Soc., 1995, 117, 8472.
12. D. S. Larsen, M. D. O'Shea and S. Brooker, Chem. Commun., 1996, 203.
13. G. Matsuo, Y. Miki, M. Nakata, S. Matsumura and K. Toshima, Chem. Commun., 1996, 225.
14. Based on a polyketide condensation, (-)-urdamycinone B had been synthesized in the first example of the asymmetric synthesis of an angucyclinone: M. Yamaguchi, T. Okuma, A. Horiguchi, C. Ikeura and T. Minami, J. Org. Chem., 1992, 57, 1647.
15. For an overview of our work, see: M. C. Carreño, Chem. Rev., 1995, 95, 1717.
16. For more recent references, see: M. C. Carreño, J. L. García Ruano, M. A. Toledo, A. Urbano, V. Stefani, C. Z. Remor and J. Fischer, J. Org. Chem., 1996, 61, 503;
17. M. C. Carreño, R. Hernández-Sánchez, J. Mahugo and A. Urbano, J. Org. Chem., 1999, 64, 1387.
18. M. C. Carreño, A. Urbano and C. Di Vitta, J. Org. Chem., 1998, 63, 8320.
19. M. C. Carreño, A. Urbano and J. Fischer, Angew. Chem., Int. Ed. Engl., 1997, 36, 1621.
20. M. C. Carreño, J. L. García Ruano and A. Urbano, Synthesis, 1992, 651.
21. D. S. Larsen and M. D. O'Shea, J. Chem. Soc., Perkin Trans. 1, 1995, 1019.
22. B. H. Lipshutz and D. F. Harvey, Synth. Commun., 1982, 12, 267.
23. K. Krohn, F. Ballwanz and W. Baltus, Liebigs Ann. Chem., 1993, 911;
24. K. Krohn, K. Khanbabaee, U. Flörke, P. G. Jones and A. Chrapkowski, Liebigs Ann. Chem., 1994, 471.