Total synthesis and structure revision of deacetylravidomycin M

Tetrahedron

Volumn 67, Issue 35, 2011, Pages 6460-6468

  Ben, Akimi ^a   Hsu, Day Shin ^a   Matsumoto, Takashi ^a,b   Suzuki, Keisuke ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

2+2 Cycloaddition; Aryl C glycoside; O C Glycoside rearrangement; Ravidomycin; Ring expansion reaction; Total synthesis

Indexed keywords

ACETIC ACID; ALICYCLIC COMPOUND; ALKOXYBENZENE DERIVATIVE; ALKOXYBENZOCYCLOBUTENONE; ANTINEOPLASTIC ANTIBIOTIC; CD23 ANTIGEN; DEACETYLRAVIDOMYCIN M; KETENE DERIVATIVE; NATURAL PRODUCT; OXIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CONTROLLED STUDY; CYCLOADDITION; ENANTIOMER; GLYCOSIDATION; HUMAN; HUMAN CELL; PRIORITY JOURNAL; RING EXPANSION REACTION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 79960934118     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.06.046     Document Type: Article

References (50)

1. Ravidomycin: J.A. Findlay, J.-S. Liu, L. Radics, and S. Rakhit Can. J. Chem. 59 1981 3018
2. J.A. Findlay, J.-S. Liu, and L. Radics Can. J. Chem. 61 1983 323
3. S.N. Sehgal, H. Czerkawski, A. Kudelski, K. Pandev, R. Saucier, and C. Vezina J. Antibiot. 36 1983 355
4. T. Narita, M. Matsumoto, K. Mogi, K. Kukita, R. Kawahara, and T. Nakashima J. Antibiot. 42 1989 347
5. Deacetylravidomycin: T. Narita, M. Matsumoto, K. Mogi, K. Kukita, R. Kawahara, and T. Nakashima J. Antibiot. 42 1989 347
6. M. Arai, H. Tomoda, A. Matsumoto, Y. Takahashi, B.H. Woodruff, N. Ishiguro, S. Kobayashi, and S. Omura J. Antibiot. 54 2001 554
7. M. Arai, H. Tomoda, N. Tabata, N. Ishiguro, S. Kobayashi, and S. Omura J. Antibiot. 54 2001 562
8. FA35A, FA35B: N. Yamashita, K. Shin-ya, K. Furihata, Y. Hayakawa, and H. Seto J. Antibiot. 51 1998 1005
9. Ravidomycin N-oxide, deacetylravidomycin N-oxide: T. Narita, M. Matsumoto, K. Mogi, K. Kukita, R. Kawahara, and T. Nakashima J. Antibiot. 42 1989 347
10. Deacetylravidomycin M: M. Arai, H. Tomoda, A. Matsumoto, Y. Takahashi, B.H. Woodruff, N. Ishiguro, S. Kobayashi, and S. Omura J. Antibiot. 54 2001 554
11. M. Arai, H. Tomoda, N. Tabata, N. Ishiguro, S. Kobayashi, and S. Omura J. Antibiot. 54 2001 562
12. J.A. Findlay, J.-S. Daljeet, P.J. Murray, and R.N. Rej Can. J. Chem. 65 1987 427
13. T.C. McKenzie, W. Hassen, and S.J.F. Macdonald Tetrahedron Lett. 28 1987 5435
14. M.E. Jung, and Y.H. Jung Tetrahedron Lett. 29 1988 2517
15. A.D. Patten, N.H. Nguyen, and S.J. Danishefsky J. Org. Chem. 53 1988 1003
16. D.J. Hart, and G.H. Merriman Tetrahedron Lett. 30 1989 5903
17. P.P. Deshpande, and O.R. Martin Tetrahedron Lett. 31 1990 6313
18. K.A. Parker, and C.A. Coburn J. Org. Chem. 56 1991 1666
19. C.A. James, and V. Snieckus Tetrahedron Lett. 38 1997 8149
20. I. Takemura, K. Imura, T. Matsumoto, and K. Suzuki Org. Lett. 6 2004 2503
21. T. Matsumoto, T. Hosoya, and K. Suzuki J. Am. Chem. Soc. 114 1992 3568
22. T. Hosoya, E. Takashiro, T. Matsumoto, and K. Suzuki J. Am. Chem. Soc. 116 1994 1004
23. S. Futagami, Y. Ohashi, K. Imura, T. Hosoya, K. Ohmori, T. Matsumoto, and K. Suzuki Tetrahedron Lett. 41 2000 1063
24. A. Ben, T. Yamauchi, T. Matsumoto, and K. Suzuki Synlett 2004 225
25. See also: T. Yamauchi, Y. Watanabe, K. Suzuki, and T. Matsumoto Synthesis 2006 2818
26. I. Takemura, K. Imura, T. Matsumoto, and K. Suzuki Tetrahedron Lett. 47 2006 6673
27. I. Takemura, T. Matsumoto, and K. Suzuki Tetrahedron Lett. 47 2006 6677
28. D.S. Hsu, T. Matsumoto, and K. Suzuki Synlett 2005 801
29. T. Hamura, T. Hosoya, H. Yamaguchi, Y. Kuriyama, M. Tanabe, M. Miyamoto, Y. Yasui, T. Matsumoto, and K. Suzuki Helv. Chim. Acta 85 2002 3589
30. S.K. Tsujiyama, and K. Suzuki Org. Synth. 84 2007 272
31. W. Ried, and M. Schoen Chem. Ber. 98 1965 3142
32. M. Jurgec, M. Kovacic, B. Stanovnik, M. Tisler, and M. Volk J. Heterocycl. Chem. 12 1975 253
33. J.J. Kulagowski, G. Mitchell, C.J. Moody, and C.W. Rees J. Chem. Soc., Chem. Commun. 1985 652
34. G. Mitchell, and C.W. Rees J. Chem. Soc., Perkin 1 1987 403
35. R.C. Cambie, P.I. Higgs, P.S. Rutledge, and P.D. Woodgate Aust. J. Chem. 47 1994 1815
36. G. Yasuda, and H. Kimoto J. Heterocycl. Chem. 35 1998 365
37. T. Kitamura, M. Todaka, I. Shin-machi, and Y. Fujiwara Heterocycl. Commun. 4 1998 205
38. T. Kitamura, N. Fukatsu, and Y. Fujiwara J. Org. Chem. 63 1998 8579
39. M.-W. Ding, G.-P. Zeng, and T.-J. Wu Synth. Commun. 30 2000 1599
40. E.F.V. Scriven, and K. Turnbull Chem. Rev. 88 1988 297
41. T. Hosoya, T. Hamura, Y. Kuriyama, M. Miyamoto, T. Matsumoto, and K. Suzuki Synlett 2000 520
42. K. Hattori, and H. Yamamoto J. Org. Chem. 58 1993 5301
43. K. Hattori, and H. Yamamoto Tetrahedron 50 1994 3099
44. M. Frigerio, and M. Santagostino Tetrahedron Lett. 35 1994 8019
45. M. Frigerio, M. Santagostino, and S. Sputore J. Org. Chem. 64 1999 4537
46. 2i However, the conversion of 21 into 22 was not reproducible. Instead, the following conditions proved suitable: N.A. Powell, and S.D. Rychnovsky Tetrahedron Lett. 37 1996 7901
47. D. Seebach, and H. Neumann Chem. Ber. 107 1974 847
48. H. Kato, K. Ohmori, and K. Suzuki Synlett 2001 1003
49. T. Hosoya, E. Takashiro, T. Matsumoto, and K. Suzuki Tetrahedron Lett. 35 1994 4591
50. T. Hosoya, E. Takashiro, Y. Yamamoto, T. Matsumoto, and K. Suzuki Heterocycles 42 1996 397