Total synthesis of (±)-xanthocidin using FeCl3-mediated Nazarov reaction

Tetrahedron

Volumn 66, Issue 52, 2010, Pages 9808-9813

  Yaji, Kentaro ^a   Shindo, Mitsuru ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

Antibiotics; Cyclopentenoid; Nazarov reaction; Total synthesis

Indexed keywords

ANTIBIOTIC AGENT; CARBENE; CYCLOPENTENONE DERIVATIVE; ESTER DERIVATIVE; FERRIC CHLORIDE; KETONE DERIVATIVE; TERT BUTYL HYDROPEROXIDE; UNCLASSIFIED DRUG; XANTHOCIDIN;

ARTICLE; CHEMICAL REACTION; DIHYDROXYLATION; DRUG SYNTHESIS; ESTERIFICATION; NAZAROV REACTION; OXIDATION; PRIORITY JOURNAL;

EID: 78649683693     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.10.084     Document Type: Article

References (91)

1. T. Haneishi, N. Kitahara, Y. Takiguchi, M. Arai, and S. Sugawara J. Antibiot. 27 1974 386
2. T. Haneishi, A. Terahara, M. Arai, T. Hata, and C. Tamura J. Antibiot. 27 1974 393
3. M. Arai, T. Haneishi, M. Nakahara, N. Kitahara, and Y. Takiguchi Jpn. Kokai Tokkyo Koho 1973 JP 48019796
4. M. Arai, T. Haneishi, M. Nakahara, N. Kitahara, and H. Takiguchi Jpn. Kokai Tokkyo Koho 1979 JP 54012556
5. For the synthesis of methylenomycin A, see
6. R.M. Scarborough Jr., and A.B. Smith III. J. Am. Chem. Soc. 99 1977 7085
7. J. Jernow, W. Tautz, P. Rosen, and J.F. Blount J. Org. Chem. 44 1979 4210
8. R.M. Scarborough Jr., B.H. Toder, and A.B. Smith III J. Am. Chem. Soc. 102 1980 3904
9. Y. Takahashi, K. Isobe, H. Hagiwara, H. Kosugi, and H. Uda J. Chem. Soc., Chem. Commun. 1981 714
10. M.A. Tius, and S. Trehan J. Org. Chem. 54 1989 46
11. For the synthesis of methylenomycin B, see
12. J. Jernow, W. Tautz, P. Rosen, and T.H. Williams J. Org. Chem. 44 1979 4212
13. K. Tonari, K. Machiya, I. Ichimoto, and H. Ueda Agric. Biol. Chem. 45 1981 295
14. R.F. Newton, D.P. Reynolds, and T. Eyre Synth. Commun. 11 1981 527
15. T. Siwapinyoyos, and Y. Thebtaranonth J. Org. Chem. 47 1982 598
16. Y. Takahashi, H. Kosugi, and H. Uda J. Chem. Soc., Chem. Commun. 1982 496
17. G.M. Strunz, and G.S. Lal Can. J. Chem. 60 1982 2528
18. M.A. Tius, D.P. Astrab, A.H. Fauq, J.B. Ousset, and S. Trehan J. Am. Chem. Soc. 108 1986 3438
19. F. Camps, J. Coll, J.M. Moreto, and J. Torras Tetrahedron Lett. 26 1985 6397
20. M. Koller, M. Karpf, and A.S. Dreiding Tetrahedron Lett. 27 1986 19
21. C.J. Rizzo, N.K. Dunlap, and A.B. Smith III J. Org. Chem. 52 1987 5280
22. J. Mathew J. Chem. Soc., Perkin Trans. 1 1991 2039 and references therein
23. P. Ceccherelli, M. Curini, M.C. Marcotullio, and O. Rosati Synth. Commun. 21 1991 17
24. M. Mikolajczyk, and A. Zatorski J. Org. Chem. 56 1991 1217 and references therein
25. P.A. Jacobi, R.O. Cann, and D.F. Skibbie Tetrahedron Lett. 33 1992 2265
26. J. Motoyoshiya, K. Mizuno, T. Tsuda, and S. Hayashi Synlett 1993 237
27. P. Bałczewski Heteroat. Chem. 8 1997 67 and references therein
28. T.A. Shevchuk, and O.G. Kulinkovich Russ. J. Org. Chem. 36 2000 1124
29. T. Yamamoto, and S. Yamaoka J. Antibiot., Ser. A 7 1954 7
30. H. Umezawa, T. Takeuchi, and K. Nitta J. Antibiot., Ser. A 6 1953 101
31. H. Umezawa, T. Yamamoto, T. Takeuchi, S. Yamaoka, K. Nitta, and Y. Okami J. Antibiot., Ser. A 6 1953 147
32. For the synthesis of sarkomycin, see
33. K. Toki Bull. Chem. Soc. Jpn. 30 1957 450
34. M.M. Shemyakin, G.A. Ravdel, E.S. Chaman, Y.B. Shvetsov, and E.I. Vinogradova Izv. Akad. Nauk. SSSR, Ser. Khim. 1959 2188
35. R.K. Boeckman Jr., P.C. Naegely, and S.D. Arthur J. Org. Chem. 45 1980 752
36. Y. Kobayashi, and J. Tsuji Tetrahedron Lett. 22 1981 4295
37. B.A. Wexler, B.H. Toder, G. Minaskanian, and A.B. Smith III J. Org. Chem. 47 1982 3333 and references therein
38. E.J. Barreiro Tetrahedron Lett. 23 1982 3605
39. A.T. Hewson, and D.T. MacPherson Tetrahedron Lett. 24 1983 647
40. S.V. Govindan, T. Hudlicky, and F.J. Koszyk J. Org. Chem. 48 1983 3581
41. M. Kodpinid, T. Siwapinyoyos, and Y. Thebtaranonth J. Am. Chem. Soc. 106 1984 4862
42. P.G. Baraldi, A. Barco, S. Benetti, G.P. Pollini, E. Polo, and D. Simoni J. Chem. Soc., Chem. Commun. 1984 1049
43. M. Mikolajczyk, and P. Balczewski Tetrahedron 45 1989 7023 and references therein
44. A. Kar, and N.P. Argade Synthesis 2005 1234
45. K. Umino, T. Furumai, N. Matsuzawa, Y. Awataguchi, Y. Ito, and T. Okuda J. Antibiot. 26 1973 506
46. K. Umino, N. Takeda, Y. Ito, and T. Okuda Chem. Pharm. Bull. 22 1974 1233
47. For the synthesis of pentenomycin, see
48. S.J. Branca, and A.B. Smith III. J. Am. Chem. Soc. 100 1978 7767
49. J.P.H. Verheyden, A.C. Richardson, R.S. Bhatt, B.D. Grant, W.L. Fich, and J.G. Moffatt Pure Appl. Chem. 50 1978 1363
50. J.M.J. Verlaak, A.J.H. Klunder, and B. Zwanenburg Tetrahedron Lett. 23 1982 5463
51. M. Hetmanski, N. Purcell, R.J. Stoodley, and M.N. Palfreyman J. Chem. Soc., Perkin Trans. 1 1984 2089 and references therein
52. T. Sugahara, and K. Ogasawara Synlett 1999 419
53. M. Seepersaud, and Y. Al-Abed Tetrahedron Lett. 41 2000 4291
54. J.K. Gallos, K.C. Damianou, and C.C. Dellios Tetrahedron Lett. 42 2001 5769
55. R.G. Venkata, and R.B. Venkateswara Tetrahedron Lett. 44 2003 5103
56. J.K. Gallos, C.I. Stathakis, S.S. Kotoulas, and A.E. Koumbis J. Org. Chem. 70 2005 6884 and references therein
57. F.A. Khan, and B. Rout Tetrahedron Lett. 47 2006 5251
58. M. Pohmakotr, S. Kambutong, P. Tuchinda, and C. Kuhakarn Tetrahedron 64 2008 6315 and references therein
59. K. Asahi, J. Nagatsu, and S. Suzuki J. Antibiot., Ser. A 19 1966 195
60. K. Asahi, and S. Suzuki Agric. Biol. Chem. 34 1970 325
61. D. Boschelli, and A.B. Smith III Tetrahedron Lett. 22 1981 3733
62. A.B. Smith III, and D. Boschelli J. Org. Chem. 48 1983 1217
63. M.A. Tius, and D.P. Astrab Tetrahedron Lett. 30 1989 2333
64. M.A. Tius, and D.J. Drake Tetrahedron 52 1996 14651
65. For the synthetic studies of xanthocidin, see
66. P.A. Jacobi, H.L. Brielmann, and R.O. Cann J. Org. Chem. 59 1994 5305
67. B.W. Au-Yeung, and Y. Wang J. Chem. Soc., Chem. Commun. 1985 825
68. K. Mori, A. Horinaka, and M. Kido Liebigs Ann. Chem. 1994 817
69. M.A. Tius, G.M.L. Patterson, and D.P. Astrab J. Antibiot. 38 1985 1061
70. For a review on torquoselective olefination, see: M. Shindo, and S. Mori Synlett 2008 2231
71. M. Shindo, K. Yaji, T. Kita, and K. Shishido Synlett 2007 1096
72. K. Yaji, and M. Shindo Synlett 2009 2524
73. K. Yaji, and M. Shindo Tetrahedron Lett. 51 2010 5469
74. For reviews, see:
75. W. Nakanishi, and F.G. West Curr. Opi. Drug Discovery Dev. 12 2009 732
76. A.J. Frontier, and C. Collison Tetrahedron 61 2005 7577
77. H. Pellissier Tetrahedron 61 2005 6479
78. M.A. Tius Eur. J. Org. Chem. 2005 2193
79. K.L. Habermas, S.E. Denmark, and T.K. Jones L.A. Paquette, Organic Reactions Vol. 45 1994 John Wiley New York, NY 1 158
80. C. Santelli-Rouvier, and M. Asantelli Synthesis 1983 429
81. For a review on ynolates, see: M. Shindo Tetrahedron 63 2007 10
82. M. Shindo, T. Kita, T. Kumagai, K. Matsumoto, and K. Shishido J. Am. Chem. Soc. 128 2006 1062
83. M. Yus, G. Radivoy, and F. Alonso Synthesis 6 2001 914
84. F. Sato, H. Ishikawa, H. Watanabe, and M. Sato J. Chem. Soc., Chem. Commun. 1981 718
85. 2, room temperature (57% yield, two steps)
86. H. Nakata Tetrahedron 19 1963 1959
87. S.F. Martin J. Chem. Soc. 1952 2682
88. J.L. Howe J. Am. Chem. Soc. 23 1901 775
89. M. Miyashita, and A. Yoshikoshi Synthesis 1980 664
90. S. Kim, Y.H. Park, and I.S. Kee Tetrahedron Lett. 32 1991 3099
91. Preparation of the α,α-dibromo esters: M. Shindo, Y. Sato, R. Koretsune, T. Yoshikawa, K. Matsumoto, K. Itoh, and K. Shishido Chem. Pharm. Bull. 51 2003 477