Enantioselective synthesis of natural polyoxygenated cyclohexanes and cyclohexenes from [(p-tolylsulfinyl)methyl]-p-quinols

Chemistry - A European Journal

Volumn 13, Issue 4, 2007, Pages 1064-1077

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

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

Asymmetric synthesis; Cyclohexanes; Cyclohexenes; Natural products; Quinols

Indexed keywords

ADDITION REACTIONS; CHEMICAL BONDS; CONFORMATIONS; ISOMERS; ORGANOMETALLICS; OXIDATION; REDUCTION; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ASYMMETRIC SYNTHESIS; CYCLOHEXANES; CYCLOHEXENES; NATURAL PRODUCTS; QUINOLS;

AROMATIC HYDROCARBONS;

CYCLOHEXANE DERIVATIVE; CYCLOHEXENE DERIVATIVE; HYDROQUINONE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

CYCLOHEXANES; CYCLOHEXENES; HYDROQUINONES; MODELS, MOLECULAR; MOLECULAR STRUCTURE;

EID: 33846615903     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200601330     Document Type: Article

References (79)

1. Reviews: a) T. Hudlicky, D. A. Entwistle, K. Pitzer, A. J. Thorpe, Chem. Rev. 1996, 96, 1195-1220
2. b) L. Agrofoglio, E. Suhas, A. Farese, R. Condom, S. R. Challand, R. A. Earl, R. Guedj, Tetrahedron 1994, 50, 10611-10670
3. c)T. Hudlicky, M. Cebulak, in Cyclitols and Their Derivatives. A Handbook of Physical, Spectral, and Synthetic Data, VCH, New York, 1993; recent references:
4. d) D. Crich, D. Grant, D.J. Wink, J. Org. Chem. 2006, 71, 4521-4524;
5. e) S. E. De Sousa, P. O'Brien, C. D. Pilgram, Tetrahedron Lett. 2001, 42, 8081-8083, and references therein.
6. Reviews: a) G. Rassu, L. Auzzas, L. Pinna, L. Battistini, C. Curti, in Studies in Natural Products Chemistry:, Bioactive Natural Products, Part J, Vol. 29 (Ed. : Atta-ur-Rahman), Elsevier Science, New York 2003, pp. 449-520
7. b) Y. Kobayashi, in Glycoscience: Chemistry and Biology, Vol. 3 (Eds.: B. Fraser-Reid, K. Tatsuta, J. Thieme), Springer, Berlin 2001, pp. 2595-2661
8. c) A. Berecibar, C. Grandjean, A. Siriwardena, Chem. Rev. 1999, 99, 779-844.
9. For a recent account, see: U. Rinner, T. Hudlicky, Synlett 2005, 365387.
10. a) J. Marco-Contelles, M. T. Molina, S. Anjum, Chem. Rev. 2004, 104, 2858-2899
11. b) Ch. Thebtaranonth, Y. Thebtaranonth, Ace. Chem. Res. 1986, 19, 84-90.
12. Reviews: a) B. C. Rossiter, N. M. Swingle, Chem. Rev. 1992, 92, 771806
13. b) A. Alexakis, P. Mangeney, Tetrahedron: Asymmetry 1990, 1, 477-511
14. c) J. K. Whitesell, Chem. Rev. 1989, 89, 1581-1590; recent references
15. d) P. de March, M. Escoda, M. Figueredo, J. Font, E. Garcia-Garcia, S. Rodriguez, Tetrahedron: Asymmetry 2000, 11, 4473-4483
16. e) D. F. Taber, T. E. Christos, M. Rahimizadeh, B. Chen, J. Org. Chem. 2001, 66, 5911-5914.
17. Recent review: A. Job, C. F. Janeck, W. Bettray, R. Peters, D. Enders, Tetrahedron 2002, 58, 2253-2329.
18. a) B. M. Trost, M. L. Crawley, C. Bom Lee, Chem. Eur. J. 2006, 12, 2171-2187
19. b) B. M. Trost, M. L. Crawley, C. Bom Lee J. Am. Chem. Soc. 2000, 722, 6120-6121.
20. See, for instance: a) S. Hanessian, V. Pham, Org. Lett. 2000, 2, 2975-2978.
21. For recent reviews on organic catalysis, see: G. Lalais, D. W. C. MacMillan, Aldrichimica Acta 2006, 39, 79-87
22. b) P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248-5286;
23. Angew. Chem. Int. Ed. 2004, 43, 5248-5286.
24. For recent references, see: a) M. C. Carreno, M. J. Sanz-Cuesta, J. Org. Chem. 2005, 70, 10036-10045
25. b) M. C. Carreno, G. Hernández-Torres, A. Urbano, F. Colobert, Org. Lett. 2005, 7, 5517-5520
26. c) M. C. Carreno, F. Colobert, R. Des Mazery, G. Solladié, A. Urbano, Org. Lett. 2005, 7, 2039-2042
27. d) M. C. Carreno, I. Garcia, M. Ribagorda, E. Merino, S. Pieraccini, G. P. Spada, Org. Lett. 2005, 7, 2869-2872
28. e) M. C. Carreno, M. González-Lopez, A. Urbano, Chem. Commun. 2005, 611-613.
29. M. C. Carreño, M. Pérez-González, M. Ribagorda, Á. Somoza, A. Urbano, Chem. Commun. 2002, 3052-3053.
30. a) M. C. Carreno, M. Pérez-González, M. Ribagorda, J. Fischer, J. Org. Chem. 1996, 61, 6758-6759
31. b) M. C. Carreno, M. Pérez-González, M. Ribagorda, K. N. Houk, J. Org. Chem. 1998, 63, 36873693.
32. a) M. C. Carreno, M. Ribagorda, A. Somoza, A. Urbano, Angew. Chem. Int. Ed. 2002, 41, 2755-2757
33. b) M. C. Carreno, M. Ribagorda, A. Somoza, A. Urbano, Chem. Eur. J. 2006, 12, DOI: 10.1002/ chem.200600809, in press.
34. Part of this work was communicated previously: M. C. Carreño, E. Merino, M. Ribagorda, A. Somoza, A. Urbano, Org. Lett. 2005, 7, 1419-1422.
35. M.-S. Kuo, D. A. Yurek, S. A. Mizsak, V. P. Marshall, W. F. Liggett, J. I. Cyaldella, A. L. Laborde, J. A. Shelly, S. E. Truesdell, J. Antibiot. 1995, 888-890.
36. G. Bach, S. Breiding-Mack, S. Grabley, P. Hammann, K. Hütter, R. Thiericke, H. Uhr, J. Wink, A. Zeeck, Liebigs Ann. Chem. 1993, 241-250.
37. Y.-Q. Tang, C. Maul, R. Hoefs, I. Sattler, S. Grabley, X.-Z. Feng, A. Zeeck, R. Thiericke, Eur. J. Org. Chem. 2000, 149-153.
38. R. Alibés, P. Bayón, P. de March, M. Figueredo, J. Font, G. Marjanet, Org. Lett. 2006, 8, 1617-1620.
39. H. Nagasawa, A. Suzuki, S. Tamura, Agric. Biol. Chem. 1978, 42, 1303-1304.
40. T. Kamikubo, K. Ogasawara, Tetrahedron Lett. 1995, 36, 1685-1688.
41. K. Hiroya, Y. Kurihara, K. Ogasawara, Angew. Chem. Int. Ed. Engl. 1995, 34, 2287-2289.
42. H. Okamura, H. Shimizu, N. Yamashita, T. Iwagawa, M. Nakatani, Tetrahedron 2003, 59, 10159-10164.
43. M. T. Barros, Ch. D. Maycock, M. R. Ventura, Chem. Eur. J. 2000, 6, 3991-3996.
44. T. Tachihara, T. Kitahara, Tetrahedron 2003, 59, 1773-1780.
45. K. Nakamori, H. Matsuura, T. Yoshihara, A. Ichihara, Y. Koda, Phytochemistry 1994, 35, 835-839.
46. H. Arimoto, T. Shimano, D. Uemura, J. Agric. Food Chem. 2005, 53, 3863-3866.
47. T. Nagata, Y. Ando, A. Hirota, Biosci. Biotechnol. Biochem. 1992, 56, 810-811.
48. T. Kamikubo, K. Ogasawara, Heterocycles 1998, 47, 69-72.
49. M. W. Miller, C. R. Johnson, J. Org. Chem. 1997, 62, 1582-1583.
50. E. Negishi, Z. Tan, S.-Y. Liou, B. Liao, Tetrahedron 2000, 56, 10197-10207.
51. A. E. Graham, D. McKerrecher, D. H. Davies, R. J. K. Taylor, Tetrahedron Lett. 1996, 37, 7445-7448.
52. a) M. C. Carrefio, M. Pérez-González, J. Fischer, Tetrahedron Lett. 1995, 36, 4893-4896
53. b) M. C. Carreno, M. Pérez-González, K. N. Houk, J. Org. Chem. 1997, 62, 9128-9137.
54. G. Solladié, J. Hutt, A. Girardin, Synthesis 1987, 173-177.
55. a) B. Belleau, N. L. Weinberg, J. Am. Chem. Soc. 1963, 85, 25252526
56. b) B. Belleau, N. L. Weinberg, Tetrahedron 1973, 29, 279-285
57. c) G. L. Buchanan, R. A. Raphael, R. Taylor, J. Chem. Soc, Perkin Trans. 1 1973, 373-375.
58. For an explanation of the stereochemical course of this reaction, see ref. [,11b].
59. For an explanation of the chemo- and diastereoselectivity of the process, see ref. [11].
60. For a review, see: a) B. Gung, Tetrahedron 1996, 52, 5263-5301
61. b) Y.-D. Wu, K. N. Houk, B. M. Trost, J. Am. Chem. Soc. 1987, 709, 5560-5561.
62. Y.-D. Wu, J. A. Tucker, K. N. Houk, J. Am. Chem. Soc. 1991, 113, 5018-5027.
63. For a similar situation, see: Y. Nagao, M. Goto, M. Ochiai, Chem. Lett. 1990, 1507-1510.
64. M. T. Barros, P. M. Matias, Ch. D. Maycock, M. R. Ventura, Org. Lett. 2003, 5, 4321-4323.
65. a) D. Yang, Acc. Chem. Res. 2004, 37, 497-505
66. b) Y. Shi, Ace. Chem. Res. 2004, 37, 488-496
67. c) L. Troisi, L. Cassidei, L. Lopez, R. Mello, R. Curci, Tetrahedron Lett. 1989, 30, 257-260.
68. a) J. B. Evarts, P. L. Fuchs, Tetrahedron Lett. 2001, 42, 3673-3675
69. b) J. B. Evarts, P. L. Fuchs, Tetrahedron Lett. 1999, 40, 2703-2706.
70. Trityl hydroperoxide was synthesized by the procedure patented by E. Haegel, DE 3701502 (1988) [Chem. Abstr. 1998, 109, 210656].
71. R = 15.3 for the (25,3S,4R,65) enantiomer (-)-S, and 17.5 min for the (2R,3R,4S,6R) enantiomer (+)-5 (211 nm).
72. B. Plietker, M. Nieggemann, A. Pollrich, Org. Biomol. Chem. 2004, 2, 1116-1124.
73. Y.-U. Kwon, C. Lee, S.-K. Ghung, J. Org. Chem. 2002, 67, 33273338.
74. T. J. Donohoe, P. R. Moore, R. L. Beddoes, J. Chem. Soc. Perkin Trans, I 1997, 43-51.
75. For a discussion on the stereoselectivity of epoxidation of cyclohexene derivatives and epoxide opening, see: M. Eipert, C. Maichle Mossmer, M. E. Maier, Tetrahedron 2003, 59, 7949-7960, and references therein.
76. J. A. Dale, H. S. Mosher, J. Am. Chem. Soc. 1973, 95, 512-519,
77. CCDC-620234 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data_request/cif.
78. K. Li, L. G. Hamann, M. Koreda, Tetrahedron Lett. 1992, 33, 65696570.
79. 3 a mixture of epimers was formed. See ref. [22].