Studies toward the synthesis of angularly-oxygenated angucyclines antibiotics

Arkivoc

Volumn 2004, Issue 13, 2004, Pages 5-16

  Lebrasseur, Nathalie ^a   Fan, Gao Jun ^b   Quideau, Stéphane ^a,b  

^a INSTITUT EUROPÉEN DE CHIMIE ET BIOLOGIE   (France)

^b UNIVERSITÉ DE BORDEAUX   (France)

Author keywords

3 iodane; Angucyclines; Aquayamycin; Cyclohexa 2,4 dienones; Dearomatization

Indexed keywords

(4A METHOXY 3 METHYL 2,3,4,4A TETRAHYDRO 3,10B EPOXYBENZO[H]CHROMEN 2 YL)METHANEDIOL; 2 (4 HYDROXY 3 METHOXY 1 NAPHTHYL) 3 METHYLBUT 2 ENAL; 2,9B DIHYDROXY 3A METHOXY 2 METHYL 2,3,3A,9B TETRAHYDRO 1H CYCLOPENTA[A]NAPHTHALENE 1 CARBALDEHYDE; 3 [(2 METHOXY 1 OXO 1,2 DIHYDRONAPHTHALEN 2 YL)METHYL] 3 METHYLOXIRANE 2 CARBALDEHYDE; 3 [DIMETHYL(PHENYL)SILYL] 3 METHYLBUTANAL; 4 (2 METHOXY 1 OXO 1,2 DIHYDRONAPHTHALEN 2 YL) 3 METHYLBUT 2 ENAL; 4 (4 HYDROXY 3 METHOXY 1 NAPHTHYL) 3 METHYLBUT 2 ENAL; 5 (2 METHOXY 1 OXO 1,2 DIHYDRONAPHTHALEN 2 YL) 4 METHYL 2 [(TRIMETHYLSILYL)OXY]PENT 3 ENENITRILE; 6A METHOXY 7A METHYL 7,7A,9,9A TETRAHYDROBENZO[H]OXETO[3,2 B]CHROMENE 9,10A(6AH) DIOL; 9B HYDROXY 3A METHOXY 2 METHYL 3A,9B DIHYDRO 3H CYCLOPENTA[A]NAPHTHALENE 1 CARBALDEHYDE; ANGUCYCLINE DERIVATIVE; ANTIINFECTIVE AGENT; AQUAYAMYCINE; BENZENE DERIVATIVE; CARBON; NAPHTHALENE DERIVATIVE; SS 228 Y; UNCLASSIFIED DRUG; VINEOMYCIN; WP 36882;

ANALYTIC METHOD; AROMATIZATION; ARTICLE; DRUG SYNTHESIS; OXYGENATION;

EID: 5144232058     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (46)

1. Rohr, J.; Thiericke, R. Nat. Prod. Rep. 1992, 9, 103-137.
2. Krohn, K.; Rohr, J. Top. Curr. Chem. 1997, 188, 127-195.
3. Guingant, A.; Barreto, M. M. Tetrahedron Lett. 1987, 28, 3107-3110.
4. Larsen, D. S.; O'Shea, M. D. J. Chem. Soc. Perkin Trans I 1995, 1019-1028.
5. Larsen, D. S.; O'Shea, M. D.; Brooker, S. Chem. Comm. 1996, 203-204.
6. Krohn, K.; Khanbabaee, K. Liebigs Ann. Chem. 1994, 1109-1112.
7. Krohn, K.; Khanbabaee, K.; Micheel, J. Liebigs Ann. Chem. 1995, 1529-1537.
8. Carreño, C. M.; Urbano, A.; Di Vitta, C. Chem. Comm. 1999, 817-818.
9. Kim, K.; Boyd, V. A.; Sobti, A.; Sulikowski, G. A. Isr. J. Chem. 1997, 37, 3-22.
10. Matsumoto, T.; Sohma, T.; Yamaguchi, H.; Kurata, S.; Suzuki, K. Tetrahedron 1995, 51, 7347-7360.
11. Boyd, V. A.; Sulikowski, G. A. J. Am. Chem. Soc. 1995, 117, 8472-8473.
12. Landells, J. S.; Larsen, D. S.; Simpson, J. Tetrahedron Lett. 2003, 44, 5193-5196.
13. Katsuura, K.; Snieckus, V. Tetrahedron Lett. 1985, 26, 9-12.
14. Katsuura, K.; Snieckus, V. Can. J. Chem. 1987, 65, 124-130.
15. Uemura, M.; Nishikawa, N.; Take, K.; Ohnishi, M.; Hirotsu, K.; Higushi, T.; Hayashi, Y. J. Org. Chem. 1983, 48, 2349-2356.
16. Gordon, D. M.; Danishefsky, S. J. J. Org. Chem. 1992, 57, 7052-7055.
17. Mitchell, A. S.; Russell, R. A. Tetrahedron 1997, 53, 4387-4410.
18. Chuang, C.-P.; Wang, S.-V. Tetrahedron Lett. 1994, 35, 4365-4366.
19. Brown, P. M.; Thomson, R. H. J. Chem. Soc. Perkin Trans. I 1976, 1976, 997-1000.
20. Krohn, K.; Böker, N.; Flörke, U.; Freund, C. J. Org. Chem. 1997, 62, 2350-2356.
21. Yamaguchi, M.; Okuma, T.; Horiguchi, A.; Ikeura, C.; Minami, T. J. Org. Chem. 1992, 57, 1647-1649.
22. Kraus, G. A.; Wan, Z. Tetrahedron Lett. 1997, 38, 6509-6512.
23. Nagatsu, T.; Ayukawa, S.; Umezawa, K. J. Antibiotics 1968, 21, 354-357.
24. Ayukawa, S.; Takeuchi, T.; Sezaki, M.; Hara, T.; Umezawa, K.; Nagatsu, T. J. Antibiotics 1968, 21, 350-353.
25. Hayaishi, O.; Okuno, S.; Fujisawa, H. Biochem. Biophys. Res. Commun. 1970, 39, 643-650.
26. Nozaki, M.; Okuno, S.; Fujisawa, H. Biochem. Biophys. Res. Commun. 1971, 44, 1109-1116.
27. Tanaka, N.; Okabe, T.; Tanaka, N.; Take, K.; Inouye, Y.; Nakamura, S.; Nakashima, H.; Yamamoto, Y. Jpn. J. Cancer. Res. 1986, 77, 324-326.
28. Henkel, T.; Zeeck, A. J. Antibiot. 1990, 43, 830-837.
29. Sekisawa, R.; Iinuma, H.; Naganawa, H.; Hamada, S.; Takeuchi, T.; Yamaizumi, J.; Umezawa, K. J. Antibiotics 1996, 49, 487-490.
30. Uchida, T.; Imoto, M.; Watanabe, Y.; Miura, K.; Dobashi, T.; Matsuda, N.; Sawa, T.; Naganawa, H.; Hamada, M.; Takeuchi, T.; Umezawa, H. J. Antibiot. 1985, 38, 1171-1181.
31. Okazaki, T.; Kitahara, T.; Okami, Y. J. Antibiot. 1975, 28, 176-184.
32. Omura, S.; Tanaka, H.; Oiwa, R.; Awaya, J.; Masuma, R.; Tanaka, K. J. Antibiot. 1977, 30, 908-916.
33. Kitahara, T.; Naganawa, H.; Okazaki, T.; Okami, Y.; Umezawa, H. J. Antibiot. 1975, 28, 280-285.
34. Krohn, K.; Frese, P.; Flörke, U. Chem. Eur. J. 2000, 6, 3887-3896.
35. Matsumoto, T.; Yamaguchi, H.; Hamura, T.; Tanabe, M.; Kuriyama, Y.; Suzuki, K. Tetrahedron Lett. 2000, 41, 8383-8387.
36. Matsumoto, T.; Yamaguchi, H.; Tanabe, M.; Yasui, Y.; Suzuki, K. Tetrahedron Lett. 2000, 41, 8393-8396.
37. Yamaguchi, H.; Konegawa, T.; Tanabe, M.; Nakamura, T.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 2000, 41, 8389-8392.
38. Quideau, S.; Looney, M. A.; Pouységu, L. Org. Lett. 1999, 1, 1651-1654.
39. Quideau, S.; Pouységu, L.; Oxoby, M.; Looney, M. A. Tetrahedron 2001, 57, 319-329.
40. Stetter, H. Angew. Chem. Int. Ed. Engl. 1976, 15, 639-712.
41. Hachishu, Y.; Bode, J. W.; Suzuki, K. J. Am. Chem. Soc. 2003, 125, 8432-8433.
42. Krohn, K.; Khanbabaee, K. Angew. Chem. Int. Ed. Engl. 1994, 33, 99-100.
43. Lipshutz, B. H.; Sclafani, J. A.; Takanami, T. J. Am. Chem. Soc. 1998, 120, 4021-4022.
44. Singh, V.; Porichu, M. Tetrahedron 1996, 52, 7087-7126.
45. Miyashita, M.; Suzuki, T.; Hoshino, M.; Yoshikoshi, A. Tetrahedron 1997, 33, 12469-12486.
46. Colvin, E. W.; Thom, I. G. Tetrahedron 1986, 42, 3137-3146.