Diastereoselective reactions at enantiomerically pure, sterically congested cyclohexanes as an entry to wailupemycins A and B: Total synthesis of (+)-wailupemycin B

Chemistry - A European Journal

Volumn 11, Issue 23, 2005, Pages 7007-7023

  Kirsch, Stefan F ^a   Bach, Thorsten ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Antibiotics; Asymmetric synthesis; Ketones; Polyketides; Total synthesis

Indexed keywords

ASYMMETRIC SYNTHESIS; POLYKETIDES; TOTAL SYNTHESIS;

ADDITION REACTIONS; ALCOHOLS; SUBSTITUTION REACTIONS;

ORGANIC COMPOUNDS;

CYCLOHEXANE DERIVATIVE; PYRONE DERIVATIVE; WAILUPEMYCIN A; WAILUPEMYCIN B;

CHEMISTRY; CONFERENCE PAPER; ELECTROSPRAY MASS SPECTROMETRY; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

CYCLOHEXANES; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; PYRONES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STEREOISOMERISM;

EID: 27944498961     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200500640     Document Type: Conference Paper

References (87)

1. N. Sitachitta, M. Gadepalli, B. S. Davidson, Tetrahedron 1996, 52, 8073-8080.
2. a) W. Fenical, Chem. Rev. 1993, 93, 1673-1683;
3. b) P. R. Jensen, W. Fenical, Annu. Rev. Microbiol. 1994, 48, 559-584.
4. a) J. Piel, K. Hoang, B. S. Moore, J. Am. Chem. Soc. 2000, 122, 5415-5416;
5. b) B. S. Moore, C. Hertweck, J. N. Hopke, M. Izumikawa, J. A. Kalaitzis, G. Nilsen, T. O'Hare, J. Piel, P. R. Shipley, L. Xiang, M. B. Austin, J. P. Noel, J. Nat. Prod. 2002, 65, 1956-1962.
6. C. Hertweck, B. S. Moore, Tetrahedron 2000, 56, 9115-9120.
7. L. Xiang, J. A. Kalaitzis, G. Nilsen, L. Chen, B. S. Moore, Org. Lett. 2002, 4, 957-960.
8. a) J. Piel, C. Hertweck, P. Shipley, D. S. Hunt, M. S. Newman, B. S. Moore, Chem. Biol. 2000, 7, 943-955;
9. b) J. A. Kalaitzis, M. Izumikawa, L. Xiang, C. Hertweck, B. S. Moore, J. Am. Chem. Soc. 2003, 125, 9290-9291.
10. a) N. Miyairi, H.-I. Sakai, T. Monomi, H. Imanaka, J. Antibiot. 1976, 29, 227-235;
11. b) Y. Tokuma, N. Miyairi, Y. Morimoto, J. Antibiot. 1976, 29, 1114-1116;
12. c) H. Seto, T. Sato, S. Urano, J. Uzawa, H. Yonehara, Tetrahedron Lett. 1976, 17, 4367-4370.
13. For a Lemieux-Johnson/Bayer-Villiger sequence, see: a) M. M. Kabat, L. M. Garofalo, A. R. Daniewski, S. D. Hutchings, W. Liu, M. Okabe, R. Radinov, Y. Zhou, J. Org. Chem. 2001, 66, 6141-6150;
14. for a Criegee rearrangement, see: b) E. G. Baggiolini, B. M. Hennessy, M. R. Uskokovic, Tetrahedron Lett. 1987, 28, 2095-2098;
15. c)S. L. Schreiber, W.-F. Liew, Tetrahedron Lett. 1983, 24, 2363-2366;
16. d) H. J. Swarts, A. Verstegen, B. J. M. Jansen, A. de Groot, Tetrahedron 1994, 50, 10083-10094.
17. S. Kirsch, T. Bach, Angew. Chem. 2003, 115, 4833-4835;
18. Angew. Chem. Int. Ed. 2003, 42, 4685-4687.
19. a) J. R. Grunwell, A. Karipides, C. T. Wigal, S.W. Heinzman, J. Parlow, J. A. Surso, L. Clayton, F. J. Fleitz, M. Daffner, J. E. Stevens, J. Org. Chem. 1991, 56, 91-95;
20. b) Y. Sugita, J.-I. Sakaki, C. Kaneko, J. Chem. Soc. Perkin Trans. 1 1992, 2855-2861.
21. a) D.B. Dess, J. C. Martin. J. Org. Chem. 1983, 48, 4155-4156;
22. b) D. B. Dess, J. C. Martin, J. Am. Chem. Soc. 1991, 113, 7277-7287;
23. c) R. K. Boeckman, Jr., P. Shao, J. J. Mullins, Org. Synth. 1999, 77, 141-149.
24. M. Sato, J.-I. Sakaki, Y. Sugita, S. Yasuda, H. Sakoda, C. Kaneko, Tetrahedron 1991, 47, 5689-5708.
25. T. Bach, S. Kirsch, Synlett 2001, 1974-1976.
26. a) M. P. Wachter, T. M. Harris, Tetrahedron 1970, 26, 1685-1694;
27. b) G. A. Poulton, T. D. Cyr, Can. J. Chem. 1982, 60, 2821-2829;
28. c) W. C. Groutas, M. A. Stanga, M. J. Brubaker, T. L. Huang, M. K. Moi, R. T. Carroll. J. Med. Chem. 1985, 28, 1106-1109.
29. a) E.J. Corey, D. Seebach, Angew. Chem. 1965, 77, 1134-1135;
30. Angew. Chem. Int. Ed. Engl. 1965, 4, 1075-1077;
31. b) D. Seebach, Synthesis 1969, 17-36;
32. c) D. Seebach, E. J. Corey, J. Org. Chem. 1975, 40, 231-237;
33. d) S. Stahl, J. Gosseleck, Synthesis 1980, 561-563;
34. for a review, see: e) B.-T. Göbel, D. Seebach, Synthesis 1977, 357-402.
35. E. J. Corey, J.-L. Gras, P. Ulrich, Tetrahedron Lett. 1976, 809-811.
36. For examples, see: a) L. E. Overman, L. T. Mendelson, J. Am. Chem. Soc. 1981, 103, 5579-5581;
37. b) S. Ando, K. P. Minor, L. E. Overman. J. Org. Chem. 1997, 62, 6379-6397.
38. a) H. Rupe, M. Refardt, Helv. Chim. Acta 1942, 25, 836-845;
39. b) E. Klein, G. Ohloff, Tetrahedron 1963, 19, 1091-1099.
40. a) T. Imamoto, Y. Sugiura, N. Takiyami, Tetrahedron Lett. 1984, 25, 4233-4236;
41. b) H.-J. Liu, B. Y. Zhu, Can. J. Chem. 1991, 69, 2008-2013.
42. a) M. Cherest, H. Felkin, Tetrahedron Lett. 1968, 9, 2205-2208;
43. b) G. Frenking, K. F. Köhler, M. T. Reetz, Angew. Chem. 1991, 103, 1167-1170;
44. Angew. Chem. Int. Ed. Engl. 1991, 30, 1146-1149.
45. For a review, see: A. H. Hoveyda, D. A. Evans, G. C. Fu, Chem. Rev. 1993, 93, 1307-1370.
46. a) O. Mitsunobu, Synthesis 1981, 1-32;
47. b) D. L. Hughes, Org. React. 1995, 42, 335-656.
48. S. Kirsch, O. Ackermann, K. Harms, T. Bach, Monatsh. Chem. 2004, 135, 713-727.
49. a) A. Yasuda, S. Tanaka, K. Oshima, H. Yamamoto, H. Nozaki, J. Am. Chem. Soc. 1974, 96, 6513-6514;
50. b) H. Yamamoto, H. Nozaki, Angew. Chem. 1978, 90, 180-186;
51. Angew. Chem. Int. Ed. Engl. 1978, 17, 169-175.
52. H. B. Henbest, R. A. L. Wilson, J. Chem. Soc. 1957, 1958-1965.
53. E. J. Corey, J. W. Suggs, Tetrahedron Lett. 1975, 16, 2647-2650.
54. a) S. Hatakeyama, H. Numata, K. Osanai, S. Takano, J. Org. Chem. 1989, 54, 3515-3517;
55. b) S. Nishiyama, Y. Ikeda, S.-i. Yoshida, S. Yamamura, Tetrahedron Lett. 1989, 30, 105-108;
56. c) J. Wang, P. Herdewijn, J. Org. Chem. 1999, 64, 7820-7827.
57. S. Kirsch, T. Bach, Synthesis 2003, 1827-1836.
58. a) K. B. Sharpless, R. C. Michaelson, J. Am. Chem. Soc. 1973, 95, 6136-6137;
59. b) K. B. Sharpless, T. R. Verhoeven, Aldrichimica Acta 1979, 12, 63-73.
60. K. E. Pfitzner, J. G. Moffatt, J. Am. Chem. Soc. 1963, 85, 3027-3028.
61. T. T. Tidwell, Org. React. 1992, 39, 297-572.
62. For reviews, see: a) A. Mengel, O. Reiser, Chem. Rev. 1999, 99, 1191-1223;
63. b) N. T. Anh, Top. Curr. Chem. 1980, 88, 145-162.
64. Examples for the use of 1,2-dichloroethane as a solvent for MEM protection at elevated temperature : a) H. Paulsen, B. Mielke, Liebigs Ann. Chem. 1990, 169-180;
65. b) D. A. Clark, F. De Riccardis, K. C. Nicolaou, Tetrahedron 1994, 50, 11391-11426;
66. c) P. A. Procopiou, E. J. Bailey, C. Chan, G. G. A. Inglis, M. G. Lester, A. R. P. Srikantha, P. J. Sidebottom, N. S. Watson, J. Chem. Soc. Perkin Trans. 1 1995, 1341-1348.
67. Synthesis of IBX: a) C. Hartmann, V. Meyer, Chem. Ber. 1893, 26, 1727-1732;
68. b) M. Frigerio, M. Santagostino, S. Sputore, J. Org. Chem. 1999, 64, 4537-4538.
69. For a review, see: T. Wirth, Angew. Chem. 2001, 113, 2893-2895:
70. Angew. Chem. Int. Ed. 2001, 40, 2812-2814.
71. a) M. Frigerio, M. Santagostino, Tetrahedron Lett. 1994, 35, 8019-8022;
72. b) S. De Munari, M. Frigerio, M. Santagostino, J. Org. Chem. 1996, 61, 9272-9279.
73. For a review, see: T. D. Nelson, R. D. Crouch, Synthesis 1996, 1031-1069.
74. a) R. Pappo, D. S. Allen, R. U. Lemieux, W. S. Johnson, J. Org. Chem. 1956, 21, 478-479;
75. b) C.-Y. Chen, D. J. Hart, J. Org. Chem. 1993, 55, 3840-3849;
76. c) P. Wipf, Y. Kim, D.M. Goldstein, J. Am. Chem. Soc. 1995, 117, 11 106-11 112.
77. Examples of Dess-Martin oxidations in presence of sodium bicarbonate: a) T. I. Richardson, S. D. Rychnovsky, Tetrahedron 1999, 55, 8977-8996;
78. b) K. C. Nicolaou, J. Jung, W. H. Yoon, K. C. Fong, H.-S. Choi, Y. He, Y.-L. Zhong, P. S. Baran, J. Am. Chem. Soc. 2002, 124, 2183-2189.
79. A. Mancuso, S.-H. Huang, D. Swern, J. Org. Chem. 1978, 43, 2480-2482.
80. E. J. Corey, G. Schmidt, Tetrahedron Lett. 1979, 20, 399-402.
81. S. V. Ley, J. Norman, W. P. Griffith, S. P. Marsden, Synthesis 1994, 639-666.
82. A. E. J. de Nooy, A. C. Besemer, H. van Bekkum, Synthesis 1996, 1153-1174.
83. A. J. Fatiadi, Synthesis 1976, 65-133.
84. J. D. More, N. S. Finney, Org. Lett. 2002, 4, 3001-3003.
85. W. C. Still, M. Kahn, A. Mitra, J. Org. Chem. 1978, 43, 2923-2925.
86. A. J. Blake, J. P. Danks, A. Harrison, J. Chem. Soc. Dalton Trans. 1998, 2335-2340.
87. M. Yasuda, K. Hayashi, Y. Koloh, I. Shibata, A. Baba, J. Am. Chem. Soc. 1998, 120, 715-721.