Asymmetric synthesis of rubiginones A2 and C2 and their 11-methoxy regioisomers

Chemistry - A European Journal

Volumn 13, Issue 3, 2007, Pages 879-890

  Carreño, M Carmen ^a   Somoza, Álvaro ^a   Ribagorda, María ^a   Urbano, Antonio ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

Antibiotics; Asymmetric synthesis; Cycloaddition; Natural products

Indexed keywords

ASYMMETRIC SYNTHESIS; CYCLOADDITION; NATURAL PRODUCTS;

ANTIBIOTICS; HYDROXYLATION; OXIDATION; POLYCYCLIC AROMATIC HYDROCARBONS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ISOMERS;

ANTHRAQUINONE DERIVATIVE; FUJIANMYCIN B; RUBIGINONE C(2); UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ANTHRAQUINONES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 33846416531     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200600809     Document Type: Article

References (96)

1. a) R. H. Thomson in Naturally Occurring Quinones IV, Blackie, London, 4th ed.1996;
2. b) for a review see: J. Rohr, R. Thiericke, Nat. Prod. Rep. 1992, 9103-137.
3. S. J. Gould, X. C. Cheng, C. Melville, J. Am. Chem. Soc. 1994, 1161800-1804, and references therein.
4. For recent review articles, see: a) K. Krohn, J. Rohr, Top. Curr. Chem. 1997, 188127-195;
5. b) M. C. Carreño, A. Urbano, Synlett 20051-25.
6. For recent references, see : a) K. Krohn, J. Micheel, M. Zukowski, Tetrahedron 2000, 564753-4758;
7. b) K. A. Parker, Q.-J. Ding, Tetrahedron 2000, 5610249-10254;
8. c) T. Rozek, J. H. Sowie, S. M. Pyke, B. W. Skelton, A. H. White, J. Chem. Soc. Perkin Trans. 1 20011826-1830;
9. d) G. A. Kraus, N. Zhang, A. Melekhov, J. H. Jensen, Synlett 2001521-522;
10. e) K. Krohn, P. Frese, Tetrahedron Lett. 2001, 42681-682;
11. f) K. Krohn, Eur. J. Org. Chem. 2002, 1351-1362, and references therein;
12. g) A. Kalogerakis, U. Groth, Org. Lett. 2003, 5843-844;
13. h) S. C. Collet, J.-F. Remi, C. Cariou, S. Laib, A. Y. Guingant, N. Quang Vu, G. Dujardin, Tetrahedron Lett. 2004, 454911-4915;
14. i) N. Lebrasseur, G.-J. Fan, S. Quideau, ARKIVOC 2004, 135-16;
15. j) N. Lebrasseur, G.-J. Fan, M. Oxoby, M. A. Looney, S. Quideau, Tetrahedron 2005, 611551-1562;
16. k) S. Dey, D. Mal, Tetrahedron Lett. 2005, 465483-5486;
17. l) N. Q. Vu, G. Dujardin, S. C. Collet, E.-A. Raiber, A. Y. Guingant, M. Evain, Tetrahedron Lett. 2005, 467669-7673;
18. m) G. A. Kraus, N. Zhang, J. Q. Wei, J. H. Jensen, Eur. J. Org. Chem. 20053040-3044.
19. For recent references, see: a) F. L. Andrews, D. S. Larsen, L. Larsen, Aust. J. Chem. 2000, 5315-24;
20. b) T. Matsumoto, H. Yamaguchi, M. Tanabe, Y. Yasui, K. Suzuki, Tetrahedron Lett. 2000, 418393-8396;
21. c) G. B. Caygill, D. S. Larsen, S. Brooker, J. Org. Chem. 2001, 667427-7431;
22. d) A. Kalogerakis, U. Groth, Synlett 20031886-1888;
23. e) K. Krohn, A. Agocs, Ch. Bäuerlein, J. Carbohydr. Chem. 2003, 22579-592;
24. f) K. Krohn, M. H. Sohrab, U. Flörke, Tetrahedron: Asymmetry 2004, 15713-718;
25. g) J. Motoyoshiya, Y. Masue, G. Iwayama, S. Yoshioka, Y. Nishii, H. Aoyama, Synthesis 20042099-2102;
26. h) K. Sato, N. Asao, Y. Yamamoto, J. Org. Chem. 2005, 708977-8981;
27. i) Ch. Kesenheimer, U. Groth, Org. Lett. 2006, 82507-2510.
28. M. Oka, H. Kamei, Y. Hamagishi, K. Tomita, T. Miyaki, M. Konishi, T. Oki, J. Antibiot. 1990, 43967-976.
29. R. W. Richards, J. P. Wu, J. Antibiot. 1985, 38513-515.
30. K. Kimura, F. Kanou, H. Koshino, M. Uramoto, M. Yoshihama, J. Antibiot. 1997, 43967-976.
31. K. Kimura, F. Kano, K. Kurosawa, M. Yoshihama, Jap. Patent, No. 06234693, 1994
32. [Chem. Abstr. 1995, 1228155].
33. M. Oka, M. Konishi, T. Oki, Tetrahedron Lett. 1990, 317473-7474.
34. For asymmetric version performed with chiral dienes, see ref. [5j] and the following: a) V. A. Boyd, G. A. Sulikowski, J. Am. Chem. Soc. 1995, 1178472-8473;
35. b) K. Kim, G. A. Sulikowski, Angew. Chem. 1995, 1072587-2589;
36. Angew. Chem. Int. Ed. Engl. 1995, 34, 2396-2398;
37. c) K. Kim, Y. Guo, G. A. Sulikowski, J. Org. Chem. 1995, 606866-6871;
38. d) D. S. Larsen, M. D. O'Shea, S. Broker, Chem. Commun. 1996203-204;
39. e) K. Kim, V. A. Boyd, A. Sobti, G. A. Sulikowski, Isr. J. Chem. 1997, 373-22; chiral Lewis acid, see:
40. f) D. S. Larsen, M. D. O'Shea, J. Org. Chem. 1996, 615681-5683;
41. g) J. S. Landells, D. S. Larsen, J. Simpson, Tetrahedron Lett. 2003, 445193-5196; for chiral dienophiles, see refs. [12, 15-17].
42. M. C. Carreño, A. Urbano, C. Di Vitta, Chem. Commun. 1999817-818.
43. M. C. Carreño, J. L. Gacía Ruano, M. A. Toledo, A. Urbano, C. Z. Remor, V. Stefani, J. Org. Chem. 1996, 61503-509.
44. a) L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105137-170;
45. Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163;
46. b) L. F. Tietze, Chem. Rev. 1996, 96115-136.
47. M. C. Carreño, A. Urbano, C. Di Vitta, J. Org. Chem. 1998, 638320-8330.
48. M. C. Carreño, A. Urbano, J. Fischer, Angew. Chem. 1997, 1091695-1697;
49. Angew. Chem. Int. Ed. Engl. 1997, 36, 1621-1623.
50. M. C. Carreño, A. Urbano, C. Di Vitta, Chem. Eur. J. 2000, 6906-913.
51. M. C. Carreño, M. Ribagorda, A. Somoza, A. Urbano, Angew. Chem. 2002, 1142879-2881;
52. Angew. Chem. Int. Ed. 2002, 41, 2755-2757.
53. We used the angucyclinone numbering (see Scheme 1) throughout the text to facilitate reading.
54. a) M. C. Carreño, M. Pérez González, M. Ribagorda, J. Fischer, J. Org. Chem. 1996, 616758-6759;
55. b) M. C. Carreño, M. Pérez González, M. Ribagorda, K. N. Houk, J. Org. Chem. 1998, 633687-3693.
56. M. C. Carreño, E. Merino, M. Ribagorda, A. Somoza, A. Urbano, Org. Lett. 2005, 71419-1422.
57. M. C. Carreño, M. Pérez-González, M. Ribagorda, A. Somoza, A. Urbano, Chem. Commun. 20023052-3053.
58. a) B. Belleau, N. L. Weinberg, J. Am. Chem. Soc. 1963, 852525-2526;
59. b) B. Belleau, N. L. Weinberg, Tetrahedron 1973, 29279-285.
60. G. L. Buchanan, R. A. Raphael, R. Taylor, J. Chem. Soc. Perkin Trans. 1 1973373-375.
61. M. C. Carreño, M. Pérez González, J. Fischer, Tetrahedron Lett. 1995, 364893-4896.
62. G. Solladié, J. Hunt, A. Giraldin, Synthesis 1987173-177.
63. This mechanistic proposal has been supported by semiempirical AM1 calculations (see ref. [20b]).
64. J. A. Dale, H. S. Mosher, J. Am. Chem. Soc. 1973, 95512-519.
65. a) W. G. Dauben, G. J. Fonken, D. S. Noyce, J. Am. Chem. Soc. 1956, 782579-2582;
66. b) B. M. Trost, J. Florez, D. J. Jebaratnam, J. Am. Chem. Soc. 1987, 109613-615;
67. c) Y.-D. Wu, J. A. tucker, K. N. Houk, J. Am. Chem. Soc. 1991, 1135018-5027;
68. d) B. W. Gung, Tetrahedron 1996, 525263-5301;
69. e) K. Ando, K. N. Houk, J. Busch, A. Menassé, U. Séquin, J. Org. Chem. 1998, 631761-1766.
70. Configuration assignment was disclosed by NOE experiments.
71. M. C. Carreño, J. L. García Ruano, A. Urbano, Synthesis 1992651-653.
72. M. E. Jung, J. A. Hagenak, J. Org. Chem. 1987, 521889-1902.
73. P. Brownbridge, I. C. Jowett, Synthesis 1988252-254.
74. R. H. Thomson, J. Org. Chem. 1951, 161082-1090.
75. T. H. Smith, H. Y. Wu, J. Org. Chem. 1982, 471974-1976.
76. a) H. Muxfeldt, Angew. Chem. 1962, 74825-828;
77. b) T. R. Kelly, J. W. Gillard, R. N. Goerner, Jr., Tetrahedron Lett. 19763873-3876;
78. c) T. R. Kelly, J. W. Gillard, R. N. Goerner, Jr., J. M. Lyding J. Am. Chem. Soc. 1977, 995513-5514;
79. d) R. K. Boeckman Jr., T. M. Dolak, K. O. Culos, J. Am. Chem. Soc. 1978, 1007098-7100;
80. e) R. K. Boeckman Jr., M. H. Delton, T. M. Dolak, T. Watanabe, M. D. Glick, J. Org. Chem. 1979, 444396-4402; for more recent work see:
81. f) L. F. Tietze, C. Güntner, G. M. Gericke, I. Schuberth, G. Bunkoczi, Eur. J. Org. Chem. 20052459-2467.
82. The same behavior was observed for the double resonance experiment on adduct 26.
83. S. C. Datta, R. W. Franck, R. Tripathy, G. J. Quigley, L. Huang, S. Chen, A. Sihaed, J. Am. Chem. Soc. 1990, 1128472-8478.
84. D. S. Larsen, M. D. O'Shea, J. Chem. Soc. Perkin Trans. 1 19951019-1028.
85. a) P. Caramella, N. G. Rondan, M. N. Paddon-Row, K. N. Houk, J. Am. Chem. Soc. 1981, 1032438-2440;
86. b) F. K. Brown, K. N. Houk, J. Am. Chem. Soc. 1985, 1071970-1978, and references therein.
87. K. Krohn, F. Ballwanz, W. Baltus, Liebigs Ann. Chem. 1993911-913.
88. [28]
89. M. J. Heileman, R. Tiedemann, H. W. Moore, J. Am. Chem. Soc. 1998, 1203801-3802.
90. K. Krohn, K. Khanbabaee, U. Flörke, P. G. Jones, A. Chrapkowski, Liebigs Ann. Chem. 1994471-477.
91. H. Ihmels, J. R. Scheffer, Tetrahedron 1999, 55885-907.
92. K. Krohn, W. Baltus, Synthesis 1986942-944.
93. G. R. Clark, M. M. Nikaido, C. K. Fair, J. Lin, J. Org. Chem. 1985, 501994-1996.
94. a) M. C. Pirrung, L. Fallon, J. Zhu, Y. R. Lee, J. Am. Chem. Soc. 2001, 1233638-3643;
95. b) M. C. Pirrung, Y. R. Lee, J. Org. Chem. 1993, 586961-6963, and references therein.
96. Ch.-K. Ryu, J.-Y. Shim, M. J. Chae, I. H. Choi, J.-Y. Han, O.-J. Jung, J. Y. Lee, S. H. Jeong, Eur. J. Med. Chem. 2005, 40438-444.