Synthesis of a spiroacetal moiety of antitumor antibiotic ossamycin by anodic oxidation

Tetrahedron

Volumn 64, Issue 40, 2008, Pages 9495-9506

  Honjo, Eriko ^a   Kutsumura, Noriki ^a   Ishikawa, Yuichi ^a   Nishiyama, Shigeru ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

Anodic oxidation; Antibiotics; Ossamycin; Spiroacetal

Indexed keywords

ACETAL DERIVATIVE; ANTINEOPLASTIC ANTIBIOTIC; OSSAMYCIN; SPIRO COMPOUND;

ACETALIZATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DEPROTECTION REACTION; DIASTEREOISOMER; DIHYDROXYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROCHEMICAL ANALYSIS; INFRARED SPECTROSCOPY; OXIDATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS;

EID: 49349117316     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.07.078     Document Type: Article

References (39)

1. Schmitz H., Jubinski S.D., Hooper I.R., Crook K.E., Price Jr. K.E., and Lein J. J. Antibiot. 18 (1965) 82-88
2. Kirst H.A., Mynderse J.S., Martin J.W., Baker P.J., Paschal J.W., Steiner J.L.R., Lobkovsky E., and Clardy J. J. Antibiot. 49 (1996) 162-167
3. Salomon A.R., Voehringer D.W., Herzenberg L.A., and Khosla C. Proc. Natl. Acad. Sci. U.S.A. 97 (2000) 14766-14771
4. Salomon A.R., Voehringer D.W., Herzenberg L.A., and Khosla C. Chem. Biol. 8 (2001) 71-80
5. Kihara T., Kusakabe H., Nakamura G., Sakurai T., and Isono K. J. Antibiot. 34 (1981) 1073-1074
6. Sakurai T., Kihara T.G., and Isono K. Acta Crystallogr. C39 (1983) 295-297
7. Kihara T., and Isono K. J. Antibiot. 36 (1983) 1236
8. Karwowski J.P., Jackson M., Maus M.L., Kohl W.L., Humphrey P.E., and Tillis P.M. J. Antibiot. 44 (1991) 1312-1317
9. Hochlowski J.E., Mullally M.M., Brill G.M., Whittern D.N., Buko A.M., Hill P., and McAlpine J.B. J. Antibiot. 44 (1991) 1318-1330
10. Burres N.S., Premachandran U., Frigo A., Swanson S.J., Mollison K.W., Fey T.A., Krause R.A., Thomas V.A., Lane B., Miller L.N., and McAlpine J.B. J. Antibiot. 44 (1991) 1331-1341
11. Kirst H.A., Larsen S.H., Paschal J.W., Occolowitz J.L., Creemer L.C., Steiner J.L.R., Lobkovsky E., and Clardy J. J. Antibiot. 48 (1995) 990-996
12. Smith R.A., Peterson W.H., and McCoy E. Antibiot. Chemother. 4 (1954) 962-970
13. Visser J., Weinauer D.E., Davis R.C., Peterson W.H., Nazarewicz W., and Ordway H. J. Biochem. Microbiol. Technol. Eng. 2 (1960) 31-48
14. Thompson R.Q., Hoehn M.M., and Higgens C.E. Antimicrob. Agents Chemother. (1961) 474-479
15. Arnoux B., Garcia-Alvarez M.C., Marazano C., Das B.C., Pascard C., Merienne C., and Staron T. J. Chem. Soc., Chem. Commun. (1978) 318-319
16. Wuthier D., Keller-Schierlein W., and Wahl B. Helv. Chim. Acta 67 (1984) 1208-1216
17. Kutsumura N., and Nishiyama S. Tetrahedron Lett. 46 (2005) 5707-5709
18. Kutsumura N., and Nishiyama S. Bull. Chem. Soc. Jpn. 79 (2006) 468-478
19. Kutsumura N., and Nishiyama S. J. Carbohydr. Chem. 25 (2006) 377-385
20. Perron F., and Albizati K.F. Chem. Rev. 89 (1989) 1617-1661
21. Hungerbühler E., Naef R., Wasmuth D., Seebach D., Loosli H.-R., and Wehrli A. Helv. Chim. Acta 63 (1980) 1960-1970
22. Yus M., Nájera C., and Foubelo F. Tetrahedron 59 (2003) 6147-6212
23. Corey E.J., and Bock M.G. Tetrahedron Lett. 16 (1975) 2643-2646
24. Takano S., Hatakeyama S., and Ogasawara K. J. Chem. Soc., Chem. Commun. (1977) 68
25. Corey E.J., and Erickson B.W. J. Org. Chem. 36 (1971) 3553-3560
26. Stork G., and Zhao K. Tetrahedron Lett. 30 (1989) 287-290
27. Porter Q.N., and Utley J.H.P. J. Chem. Soc., Chem. Commun. (1978) 255-256
28. Platen M., and Steckhan E. Tetrahedron Lett. 21 (1980) 511-514
29. Cristau H.J., Chabaud B., and Niangoran C. J. Org. Chem. 48 (1983) 1527-1529
30. Lebouc A., Simonet J., Gelas J., and Dehbi A. Synthesis (1987) 320-321
31. Martre A.-M., Mousset G., Rhlid R.B., and Veschambre H. Tetrahedron Lett. 31 (1990) 2599-2602
32. Mori K., and Sku Y.-B. Tetrahedron 44 (1988) 1035-1038
33. Sasaki M., Tanino K., and Miyashita M. Org. Lett. 3 (2001) 1765-1767
34. Dounay A.B., Urbanek R.A., Frydrychowski V.A., and Forsyth C.J. J. Org. Chem. 66 (2001) 925-938
35. Shiina I., Shibata J., Ibuka R., Imai Y., and Mukaiyama T. Bull. Chem. Soc. Jpn. 74 (2001) 113-122
36. Martinelli M.J., Vaidyanathan R., Pawlak J.M., Nayyar N.K., Dhokte U.P., Doecke C.W., Zollars L.M.H., Moher E.D., Khau V.V., and Košmrlj B. J. Am. Chem. Soc. 124 (2002) 3578-3585
37. Amano Y., Inoue K., and Nishiyama S. Synlett (2008) 134-136
38. Amano Y., and Nishiyama S. Tetrahedron Lett. 47 (2006) 6505-6507
39. Smith A.B., Chen S.S.-Y., Nelson F.C., Reichert J.M., and Salvatore B.A. J. Am. Chem. Soc. 117 (1995) 12013-12014