Functionality propagation by alkylative oxidation of cross-conjugated cycloheptadienyl sulfones

Angewandte Chemie - International Edition

Volumn 42, Issue 27, 2003, Pages 3124-3131

  Torres, Eduardo ^a   Chen, Yuzhong ^a   Kim, In Chul ^a   Fuchs, P L ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

Epoxidation; Polypropionates; Stereoselectivity; Sulfones; Synthetic methods

Indexed keywords

OXIDATION; REACTION KINETICS;

NUCLEOPHILIC METHYLATION;

SULFUR COMPOUNDS;

APOPTOLIDIN; CONCANAMYCIN F; DISCODERMOLIDE; MANGANESE; MOLYBDENUM; OSMIUM; RHIZOXIN; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHIRALITY; CONJUGATION; EPOXIDATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGENATION; METHYLATION; OXIDATION; STEREOCHEMISTRY; SYNTHESIS; X RAY DIFFRACTION;

EID: 0042812113     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200350955     Document Type: Article

References (110)

1. P. L. Fuchs, Tetrahedron 2001, 57, 6855-6875.
2. Synthesis via vinyl sulfones 87; Chiral Carbon Collection 11.
3. a) Z. Tong, Y. Chen, M. F. Hentemann, P. L. Fuchs, Tetrahedron Lett. 2000, 41, 7795-7799;
4. b) M. F. Hentemann, P. L. Fuchs, Org. Lett. 1999, 1, 355 -357;
5. c) J. Evarts, E. Torres, P. L. Fuchs, J. Am. Chem. Soc. 2002, 124, 11093-11101.
6. D. Myers, P. L. Fuchs, J. Org. Chem. 2002, 67, 200-204. The 2-phenylsulfonyl-1,3-cycloheptadiene 2 and both enantiomers of 3 will soon be available from Aldrich.
7. M. F. Hentemann, P. L. Fuchs, Tetrahedron Lett. 1997, 38, 5615-5618.
8. W. Jiang, D. A. Lantrip, P. L. Fuchs, Org. Lett. 2000, 2, 2181-2184.
9. a) B. M. Trost, M. R. Ghadiri, Bull. Soc. Chim. Fr. 1993, 130, 433-442;
10. b) D. Craig, C. J. Etheridge, Tetrahedron Lett. 1993, 34, 7487-7488;
11. c) M. Harmata, V. R. Fletcher, R. J. Claassen II, J. Am. Chem. Soc. 1991, 113, 9861-9862.
12. a) S. H. Kim, Z. Jin, P. L. Fuchs, Tetrahedron Lett. 1995, 36, 4537-4538;
13. b) Z. Jin, P. L. Fuchs, J. Am. Chem. Soc. 1995, 117, 3022-3028;
14. c) Z. Jin, P. L. Fuchs, J. Am. Chem. Soc. 1994, 116, 5995-5996.
15. a is optimal for the aryl sulfone moiety.
16. 5 times less reactive than chloride as leaving groups. A. K. Colter, R. E. Miller, J. Org. Chem. 1971, 36, 1898-1903. β-Sulfonyl ketones, homoallyl, homopropargyl, and homobenzyl sulfones, having an allylically activated C-H π bond or α-heteroatom-substituted sulfones are competent leaving groups. The reaction shown in Scheme 3 is a vinylogous example of the latter case.
17. For an example of intramolecular silylation of the oxygen atom of a sulfone, see: P. C. Van Dort, P. L. Fuchs, J. Am. Chem. Soc. 1994, 116, 5657-5661.
18. For examples in which the siloxy groups appear to direct the reaction, see: J. Clayden, M. Julia, Synlett 1995, 103-104.
19. For alternative ring-cleavage approaches to synthesis of six- and especially seven-carbon sequences bearing multiple stereocenters, see the following leading references: a) M. Lautens, J. T. Colucci, S. Hiebert, N. D. Smith, G. Bouchain, Org. Lett. 2002, 4, 1879-1882;
20. b) O. Arjona, R. Menchaca, J. Plumet, J. Org. Chem. 2001, 66, 2400-2413;
21. c) O. Arjona, R. Menchaca, J. Plumet, Org. Lett. 2001, 3, 107-109;
22. d) P. Vogel, J. Cossy, J. Plumet, O. Arjona, Tetrahedron 1999, 55, 13 521-13642;
23. e) P. Vogel, A.-F. Sevin, P. Kernen, M. Bialecki, Pure. Appl. Chem. 1996, 68, 719-722;
24. f) M. Bialecki, P. Vogel, Helv. Chim. Acta 1995, 78, 325-343;
25. g) M. Lautens, Pure. Appl. Chem. 1992, 64, 1873-1882.
26. X-ray data has been submitted to the Cambridge Crystallographic database.
27. C. Lehmann, B. Schweizer, C. Leumann, A. Eschenmoser, Helv. Chim. Acta 1997, 80, 1421-1442.
28. S. Siwasaki, H. Kobayashi, J. Furukawa, M. Namikoshi, S. Okuda, Z. Sato, I. Matsuda, T. Noda, J. Antibiot. 1984, 37, 354-362.
29. S. Kaplan, A.R. Hanauske, N. Pavlidis, U. Bruntsch, A. Te Velde, J. Wanders, B. Heinrich, J. Verweij, Br. J. Cancer 1996, 73, 403-405.
30. M. Nakada, J. Synth. Org. Chem. Jpn. 1995, 53, 122-137.
31. a) M. Nakada, S. Kobayashi, S. Iwasaki, M. Ohno, Tetrahedron Lett. 1993, 34, 1035-1038;
32. b) M. Nakada, S. Kobayashi, M. Shibasaki, S. Iwasaki, M. Ohno, Tetrahedron Lett. 1993, 34, 1039-1042;
33. c) A. V. Rama Rao, G. V. M. Sharma, M. N. Bhanu, Tetrahedron Lett. 1992, 33, 3907-3910;
34. d) A. V. Rama Rao, M. N. Bhanu, G. V. M. Sharma, Tetrahedron Lett. 1993, 34, 707-710;
35. e) G. F. Keck, M. Park, D. Krishnamurthy, J. Org. Chem. 1993, 58, 3787-3788;
36. f) G. E. Keck, K. A. Savin, M. A. Weglarz, E. N. K. Cressman, Tetrahedron Lett. 1996, 37, 3291-3294;
37. g) A. S. Kende, B. E. Blass, J. R. Henry, Tetrahedron Lett. 1995, 36, 4741-4744;
38. h) J. A. Lafontaine, J. W. Leahy, Tetrahedron Lett. 1995, 36, 6029-6032;
39. i) D. Provencal, C. Gardelli, J. A. Lafontaine, J. W. Leahy, Tetrahedron Lett. 1995, 36, 6033-6036;
40. j) J. A. Lafontaine, D. Provencal, C. Gardelli, J. W. Leahy, Tetrahedron Lett. 1999, 40, 4145-4148;
41. k) D.R. Williams, K. M. Werner, B. Feng, Tetrahedron Lett. 1997, 38, 6825-6828.
42. P. A. Grieco, Y. Dai, Tetrahedron Lett. 1998, 39, 6997.
43. C. R. Johnson, A. Golebiowski, D. H. Steensma, M. A. Scialdone, J. Org. Chem. 1993, 58, 7185-7194.
44. W. Adam, L. Hadjiarapoglou, X. Wang, Tetrahedron Lett. 1989, 30, 6497-6500.
45. a) T. Maki, F. Iwasaki, Y. Matsumura, Tetrahedron Lett. 1998, 39, 5601-5604;
46. b) A. Gateau-Olesker, J. Clephax, S. D. Gero, Tetrahedron Lett. 1986, 27, 41-44;
47. c) M. J. Martinelli, N. K. Nayyar, E. D. Moher, U. P. Dhokte, J. M. Pawlak, R. Vaidyanathan, Org. Lett. 1999, 1, 447-450.
48. D. L. Cheney, L. A. Paquette, J. Org. Chem. 1989, 54, 3334-3347.
49. a) K. Toshima, T. Jyojima, H. Yamaguchi, Y. Noguchi, T. Yoshida, H. Murase, M. Nakata, S. Matsumura, J. Org. Chem. 1997, 62, 3271-3284;
50. b) K. A. Scheidt, A. Tasaka, T. D. Bannister, M. D. Wendt, W. R. Roush, Angew. Chem. 1999, 111, 1760-1762; Angew. Chem. Int. Ed. 1999, 38, 1652-1655;
51. b) K. A. Scheidt, A. Tasaka, T. D. Bannister, M. D. Wendt, W. R. Roush, Angew. Chem. 1999, 111, 1760-1762; Angew. Chem. Int. Ed. 1999, 38, 1652-1655;
52. c) D. A. Evans, M. A. Calter, Tetrahedron Lett. 1993, 34, 6871-6874.
53. a) K. Makino, N. Nakajima, S.-i. Hashimoto, O. Yonemitsu, Tetrahedron Lett. 1996, 37, 9077-9080;
54. b) S. Hanessian, A. Tehim, Q. Meng, K. Granberg, Tetrahedron Lett. 1996, 37, 9001-9004.
55. S. Gagliardi, P. A. Gatti, P. Belfiore, A. Zocchetti, G. D. Clarke, C. Farina, J. Med. Chem. 1998, 41, 1883-1893.
56. a) K. Toshima, T. Jyojima, N. Miyamoto, M. Katohno, M. Nakata, S. Matsumura, J. Org. Chem. 2001, 66, 1708-1715;
57. b) T. Jyojima, N. Miyamoto, M. Katohno, M. Nakata, S. Matsumura, K. Toshima, Tetrahedron Lett. 1998, 39, 6007-6010;
58. c) T. Jyojima, M. Katohno, N. Miyamoto, M. Nakata, S. Matsumura, K. Toshima, Tetrahedron Lett. 1998, 39, 6003-6006.
59. I. Paterson, V. A. Doughty, M. D. McLeod, T. Trieselmann, Angew. Chem. 2000, 112, 1364-1368; Angew. Chem. Int. Ed. 2000, 39, 1308-1312.
60. I. Paterson, V. A. Doughty, M. D. McLeod, T. Trieselmann, Angew. Chem. 2000, 112, 1364-1368; Angew. Chem. Int. Ed. 2000, 39, 1308-1312.
61. a) J. D. Pennington, H. J. Williams, A. R. Salomon, G. A. Sulikowski, Org. Lett. 2002, 4, 3823-3825;
62. b) P. A. Wender, A. V. Gulledge, O. D. Jankowski, H. Seto, Org. Lett. 2002, 4, 3819-3822;
63. c) A. R. Salomon, D. W. Voehringer, L. A. Herzenberg, C. Khosla, Proc. Natl. Acad. Sci. USA 2000, 97, 14766-14771;
64. d) A. R. Salomon, D. W. Voehringer, L. A. Herzenberg, C. Khosla, Chem. Biol. 2001, 8, 71-80;
65. e) J. Schuppan, H. Wehlan, S. Keiper, U. Koert, Angew. Chem. 2001, 113, 2125-2128; Angew. Chem. Int. Ed. 2001, 40, 2063-2066;
66. e) J. Schuppan, H. Wehlan, S. Keiper, U. Koert, Angew. Chem. 2001, 113, 2125-2128; Angew. Chem. Int. Ed. 2001, 40, 2063-2066;
67. f) K. C. Nicolaou, Y. Li, K. C. Fylaktakidou, H. J. Mitchell, K. Sugita, Angew. Chem. 2001, 113, 3968-3972; Angew. Chem. Int. Ed. 2001, 40, 3854-3857;
68. f) K. C. Nicolaou, Y. Li, K. C. Fylaktakidou, H. J. Mitchell, K. Sugita, Angew. Chem. 2001, 113, 3968-3972; Angew. Chem. Int. Ed. 2001, 40, 3854-3857;
69. g) K. C. Nicolaou, Y. Li, K. C. Fylaktakidou, H. J. Mitchell, H.-X. Wei, B. Weyershausen, Angew. Chem. 2001, 113, 3791-3795; Angew. Chem. Int. Ed. 2001, 40, 3849-3854;
70. g) K. C. Nicolaou, Y. Li, K. C. Fylaktakidou, H. J. Mitchell, H.-X. Wei, B. Weyershausen, Angew. Chem. 2001, 113, 3791-3795; Angew. Chem. Int. Ed. 2001, 40, 3849-3854;
71. h) A. R. Salomon, Y. Zhang, H. Seto, C. Khosia, Org. Lett. 2001, 3, 57-59;
72. i) G. A. Sulikowski, W.-M. Lee, B. Jin, B. Wu, Org. Lett. 2000, 2, 1439-1442;
73. j) J. Schuppan, B. Ziemer, U. Koert, Tetrahedron Lett. 2000, 41, 621-624;
74. k) K. C. Nicolaou, Y. Li, B. Weyershausen, H.-x. Wei, Chem. Commun. 2000, 307-308;
75. l) M. Kinoshita, H. Takami, M. Taniguchi, T. Tamai, Bull. Chem. Soc. Jpn. 1987, 60, 2151-2161;
76. m) Y. Hayakawa, J. W. Kim, H. Adachi, K. Shin-ya, K.-i. Fujita, H. Seto, J. Am. Chem. Soc. 1998, 120, 3524-3525.
77. K. C. Nicolaou, Y. Li, B. Weyershausen, H. Wei, Chem. Commun. 2000, 307-308.
78. a) S. P. Gunasekera, M. Gunasekera, E. Longley, G. K. Schulte, J. Org. Chem. 1990, 55, 4912-4915;
79. b) R. J. Kowalski, P. Giannakakou, S. P. Gunasekera, R. E. Longley, B. W. Day, E. Hamel, Mol. Pharmacol. 1997, 52, 613-622;
80. c) E. Ter Haar, R. J. Kowalski, E. Hamel, C. M. Lin, R. E. Longley, S. P. Gunasekera, H. S. Rosenkranz, B. W. Day, Biochemistry 1996, 35, 243-250.
81. a) P. Giannakakou, T. Fojo, Clin. Cancer Res. 2000, 6, 1613-1615;
82. b) L. A. Martello, H. M. McDaid, D. L. Regl, C.-P. H. Yang, D. Meng, T. R. R. Pettus, M. D. Kaufman, H. Arimoto, S. J. Danishefsky, A. B. Smith III, S. B. Horwitz, Clin. Cancer Res. 2000, 6, 1978-1987.
83. a) I. Paterson, G. J. Florence, K. Gerlach, J. P. Scott, N. Sereinig, J. Am. Chem. Soc. 2001,123, 9535-9544;
84. b) S. A. Filla, J. J. Song, L. Chen, S. Masamune, Tetrahedron Lett. 1999, 40, 5449-5453;
85. c) J. A. Marshall, B. A. Johns, J. Org. Chem. 1998, 63, 7885-7892;
86. d) J. A. Marshall, Z. Lu, B. A. Johns, J. Org. Chem. 1998, 63, 817-823;
87. e) S. S. Harried, G. Yang, A. Strawn, D. C. Myles, J. Org. Chem. 1997, 62, 6098-6099;
88. f) D. L. Clark, C. H. Heathcock, J. Org. Chem. 1993, 58, 5878-5879;
89. g) I. Paterson, S. P. Wren, J. Chem. Soc. Chem. Commun. 1993, 1790-1792;
90. h) I. Paterson, A. Schlapbach, Synlett 1995, 498-500;
91. i) G. Yang, D. C. Myles, Tetrahedron Lett. 1994, 35, 1313-1316;
92. j) G. Yang, D. C. Myles, Tetrahedron Lett. 1994, 35, 2503-2504;
93. k) J. M. C. Golec, S. D. Jones, Tetrahedron Lett. 1993, 34, 8159-8162;
94. l) J. M. C. Golec, R. J. Gillespie, Tetrahedron Lett. 1993, 34, 8167-8168;
95. m) P. L. Evans, J. M. C. Golec, R. J. Gillespie, Tetrahedron Lett. 1993, 34, 8163-8166;
96. n) S. S. Harried, G. Yang, M. A. Strawn, D. C. Myles, J. Org. Chem. 1997, 62, 6098-6099;
97. o) D. T. Hung, J. B. Nerenberg, S. L. Schreiber, J. Am. Chem. Soc. 1996, 118, 11054-11080;
98. p) A. B. Smith III, T. J. Beauchamp, M. J. LaMarche, M. D. Kaufman, Y. Qiu, H. Arimoto, D. R. Jones, K. Kobayashi, J. Am. Chem. Soc. 2000, 122, 8654-8664;
99. q) I. Paterson, S. P. Wren, J. Chem. Soc. Chem. Commun. 1993, 1790-1792;
100. r) I. Paterson, A. Schlapbach, Synlett 1995, 498-500;
101. s) I. Paterson, G. J. Florence, Tetrahedron Lett. 2000, 41, 6935-6939.
102. a) A. B. Smith III, T. J. Beauchamp, M. J. LaMarche, M. D. Kaufman, Y. Qiu, H. Arimoto, D. R. Jones, K. Kobayashi, J. Am. Chem. Soc. 2000, 122, 8654-8664;
103. b) M. J. Tomaszewski, Chem. Eur. J. 1996, 2, 847-868;
104. c) G. Godjoian, V. R. Wang, A. M. Ayala, R. V. Martinez, R. Martinez-Bernhardt, C. G. Gutierrez, Tetrahedron Lett. 1996, 37, 433-436;
105. d) P. K. Richter, H. Khatuya, P. Bertinato, R. A. Miller, N. Nagashima, M. Ohno, Chem. Lett. 1987, 141-144.
106. a) T. F. Molinski, Tetrahedron Lett. 1996, 37, 7879-7880;
107. b) P. A. Searle, T. F. Molinski, J. Am. Chem. Soc. 1996, 118, 9422-9423;
108. c) P. A. Searle, T. F. Molinski, J. Am. Chem. Soc. 1995, 117, 8126-8131.
109. B. M. Trost, Angew. Chem. 1995, 107, 285; Angew. Chem. Int. Ed. Engl. 1995, 34, 259-281.
110. B. M. Trost, Angew. Chem. 1995, 107, 285; Angew. Chem. Int. Ed. Engl. 1995, 34, 259-281.