Diversity-oriented approach to biologically relevant molecular frameworks starting with β-naphthol and using the claisen rearrangement and olefin metathesis as key steps

Chemistry - A European Journal

Volumn 12, Issue 31, 2006, Pages 8024-8038

  Kotha, Sambasivarao ^a   Mandai, Kalyaneswar ^a   Tiwari, Arti ^a   Mobin, Shaikh M ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

Author keywords

Claisen rearrangement; Diversity oriented synthesis; Meta thesis; Naphthoxepines; Spiro compounds

Indexed keywords

DERIVATIVES; NITROGEN COMPOUNDS; OLEFINS; PHASE TRANSITIONS;

CLAISEN REARRANGEMENT; DIVERSITY-ORIENTED SYNTHESIS; META-THESIS; NAPHTHOXEPINES; SPIRO COMPOUNDS;

MOLECULAR DYNAMICS;

2 NAPHTHOL; 2-NAPHTHOL; ALKENE; NAPHTHOL DERIVATIVE; OXEPINE DERIVATIVE;

ARTICLE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

ALKENES; COMBINATORIAL CHEMISTRY TECHNIQUES; NAPHTHOLS; OXEPINS;

EID: 33750552076     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200600540     Document Type: Article

References (134)

1. a) S. L. Schreiber, Science 2000, 287, 1964-1969;
2. b) M. D. Burke, S. L. Schreiber, Angew. Chem. 2004, 116, 48-60;
3. Angew. Chem. Int. Ed. 2004, 43, 46-58;
4. c) D. Tejedor, D. Gonzalez-Cruz, A. Santos-Exposito, J. J. Marrero-Tellado, P. de Armas, F. García-Tellado, Chem. Eur. J. 2005, 11, 3502-3510;
5. d) D. S. Tan, Nat. Chem. Biol. 2005, 1, 74-84;
6. e) H.-F. Chow, J. Zhang, Chem. Eur. J. 2005, 11, 5817-5831.
7. a) D. Lee, J. K. Sello, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 10648-10649;
8. b) Y. Liao, Y. Hu, J. Wu, Q. Zhu, M. Donovan, R. Fathi, Z. Yang, Curr. Med. Chem. 2003, 10, 2285-2316.
9. K. Carl, L. Joseph, U. S. Patent 4073912, 1972
10. [Chem. Abstr. 1978, 89, 24156].
11. V. K. Tandon, M. Kumar, A. K. Awasthi, H. O. Saxena, G. K. Goswamy, Bioorg. Med. Chem. Lett. 2004, 14, 3177-3180.
12. T. Sugaya, N. Kato, A. Sakaguchi, S. Tomioka, Synthesis 1995, 1257-1262, and references therein.
13. S. Vincent, S. Chen, D. B. Wilson, B. Ganem, Bioorg. Med. Chem. Lett. 2002, 72, 929-931.
14. P. S. Manchand, J. F. Blount, J. Chem. Soc. Chem. Commun. 1975, 894-895.
15. L. E. Overman, D. J. Ricca, V. D. Tran, J. Am. Chem. Soc. 1997, 119, 12031-12040.
16. B. K. Trivedi, A. Holmes, T. S. Purchase, A. D. Essenburg, K. L. Haelehle, B. R. Krause, M. K. S. Hes, R. L. Stanfield, Bioorg. Med. Chem. Lett. 1995, 5, 2229-2234.
17. Z. Xi, G. B. Jones, G. Qabaja, J. Wright, F. Johnson, I. H. Goldberg, Org. Lett. 1999, 1, 1375-1377.
18. For recent reviews on Claisen rearrangement see: a) B. Werschkun, J. Thiem, Top. Curr. Chem. 2001, 215, 293-325;
19. b) M. Hiersemann, L. Abraham, Eur. J. Org. Chem. 2002, 1461-1471;
20. c) Y. Chai, S. Hong, H. A. Lindsay, C. McFarland, M. C. McIntosh, Tetrahedron 2002, 58, 2905-2928;
21. d) U. Nubbemeyer, Synthesis 2003, 961-1008;
22. e) A. M. Castro, Chem. Rev. 2004, 104, 2939-3002;
23. For selected examples of Claisen rearrangements see: f) V. A. Smit, S. I. Pogrebnoi, Y. B. Kal'yan, M. Z. Krimer, Izv. Akad. Nauk SSSR, Ser. Khim. 1990, 1934-1935
24. [Chem. Abstr. 1990, 114, 23481];
25. g) S. I. Pogrebnoi, Y. B. Kal'yan, M. Z. Krimer, V. A. Smit, Izv. Akad. Nauk SSSR, Ser. Khim. 1991, 835-842
26. [Chem. Abstr. 1991, 115, 49277];
27. h) L. M. Harwood, A. J. Oxford, C. Thomson, J. Chem. Soc. Chem. Commun. 1991. 1303-1305;
28. i) V. T. Nguyen, S. Debenedetti, N. De Kimpe, Tetrahedron Lett. 2003, 44, 4199-4201;
29. j) B. Sreedhar, V. Swapna, C. Sridhar, Synth. Commun. 2004, 34, 1433-1440;
30. k) L. Abraham, M. Koerner, M. Hiersemann, Tetrahedron Lett. 2004, 45, 3647-3650.
31. For a preliminary communication, see: S. Kotha, K. Mandal, Tetrahedron Lett. 2004, 45, 1391-1394.
32. a) P. Schwab, R. H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100-110;
33. b) M. Scholl, S. Ding, C. W. Lee, R. H. Grubbs, Org. Lett. 1999, 7, 953-956;
34. c) S. B. Garber, J. S. Kingsbury, B. L. Gray, A. H. Hoveyda, J. Am. Chem. Soc. 2000, 122, 8168-8179.
35. a) Handbook of Metathesis, Vols. 1-3 (Ed.: R. H. Grubbs), Wiley-VCH, Weinheim, 2003;
36. For some selected reviews on olefin meta-thesis, see: b) A. J. Phillips, A. D. Abell, Aldrichimica Acta 1999, 32, 75-89;
37. c) A. Fürstner, Angew. Chem. 2000,112, 3140-3172;
38. Angew. Chem. Int. Ed. 2000, 39, 3012-3043;
39. d) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29;
40. e) S. Kotha, N. Sreenivasachary, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2001, 40B, 763-780;
41. f) R. R. Schrock, A. H. Hoveyda, Angew. Chem. 2003, 115, 4740-4782;
42. Angew. Chem. Int. Ed. 2003, 42, 4592-4633;
43. g) S. J. Connon, S. Blechert, Angew. Chem. 2003, 115, 1944-1968;
44. Angew. Chem. Int. Ed. 2003, 42, 1900-1923;
45. h) R. H. Grubbs, Tetrahedron 2004, 60, 7117-7140;
46. i) M. D. McReynolds, J. M. Dougherty, P. R. Hanson, Chem. Rev. 2004, 104, 2239-2258;
47. j) K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. 2005, 117, 4564-4601;
48. Angew. Chem. Int. Ed. 2005, 44, 4490-4527.
49. For some related examples in this area, see: k) A. Srikrishna, M.S. Rao, S. J. Gharpure, N. C. Babu, Synlett 2001, 1986-1988;
50. l) S. K. Chattopadhyay, S. Maity, S. Panja, Tetrahedron Lett. 2002, 43, 7781-7783;
51. P. Beaulieu, W. W. Ogilvie, Tetrahedron Lett. 2003, 44, 8883-8885;
52. n) V. T. Nguyen, N. De Kimpe, Tetrahedron Lett. 2004, 45, 3443-3446;
53. o) S. Kotha, K. Mandai, Tetrahedron Lett. 2004, 45, 2585-2588;
54. p) T. W. Tsai, E. C. Wang, S. R. Li, Y. H. Chen, Y. L. Lin, Y. F. Wang, K. S. Huang, J. Chin. Chem. Soc. 2004, 57, 1307-1318;
55. q) S. K. Chattopadhyay, R. Dey, S. Biswas, Synthesis 2005, 403-406;
56. r) K. S. Huang, S. R. Li, Y. F. Wang, Y. L. Lin, Y. H. Chen, T. W. Tsai, C. H. Yang, E. C. Wang, J. Chin. Chem. Soc. 2005, 52, 159-167;
57. s) V. Gracias, A. F. Gasiecki, S.W. Djuric, Tetrahedron Lett. 2005, 46, 9049-9052;
58. t) V. T. H. Nguyen, E. Bellur, P. Langer, Tetrahedron Lett. 2006, 47, 113-116;
59. u) V. T. H. Nguyen, E. Bellur, P. Langer, Tetrahedron Lett. 2006,47,113-116.
60. For reviews on enyne metathesis, see: a) M. Mori, Top. Organomet. Chem. 1998, 1, 133-154;
61. b) C. S. Poulsen, R. Madsen, Synthesis 2003, 1-18;
62. c)A.J. Giessert, S. T. Diver, Chem. Rev. 2004, 104, 1317-1382;
63. d) S. V. Maifeld, D. Lee, Chem. Eur. J. 2005, 11, 6118-6126.
64. For some selected examples related to enyne metathesis, see: a) S. Rodriguez-Conesa, P. Candal, C. Jiménez, J. Rodriguez, Tetrahedron Lett. 2001, 42, 6699-6702;
65. b) L. Ackermann, C. Bruneau, P. H. Dixneuf, Synlett 2001, 397-399;
66. c) W. A. L. van Otterlo, E. L. Ngidi, C. B. de Koning, M. A. Fernandes, Tetrahedron Lett. 2004, 45, 659-662;
67. d) P. Dewi, S. Randl, S. Blechert, Tetrahedron Lett. 2005, 46, 577-580;
68. e) M. D. Middleton, S. T. Diver, Tetrahedron Lett. 2005, 46, 4039-4043;
69. f) Y. K. Yang, J. H. Choi, J. Tae, J. Org. Chem. 2005, 70, 6995-6998.
70. Some selected examples from our group, see: g) S. Kotha, N. Sreenivasachary, E. Brahmachary, Tetrahedron Lett. 1998, 39, 2805-2808;
71. h) S. Kotha, N. Sreenivasachary, Chem. Commun. 2000, 503-504;
72. i) S. Kotha, S. Halder, E. Brahmachary, T. Ganesh, Synlett 2000, 853-855;
73. j) S. Kotha, N. Sreenivasachary, E. Brahmachary, Eur. J. Org. Chem. 2001, 787-792;
74. k) S. Kotha, N. Sreeni vasachary, Eur. J. Org. Chem. 2001, 3375-3383;
75. l) S. Kotha, S. Halder, E. Brahmachary, Tetrahedron 2002, 58, 9203-9208.
76. Reviews: a) S. Caddick, Tetrahedron 1995, 51, 10403-10432;
77. b) S. Deshayes, M. Liagre, A. Loupy, J. Luche, A. Petit, Tetrahedron 1999, 55, 10851-10870;
78. c)P. Lidstrom, J. Tierney, B. Wathey, J. Westman, Tetrahedron 2001, 57, 9225-9283;
79. d) A. Kirschning, H. Monenschein, R. Wittenberg, Angew. Chem. 2001, 113, 670-701;
80. Angew. Chem. Int. Ed. 2001, 40, 650-679;
81. e) R. S. Varma, Pure Appl. Chem. 2001, 73, 193-198;
82. f) A. Loupy, Microwaves in Organic Synthesis; Wiley-VCH, Weinheim, 2002.
83. a) P. Diddams, M. Butters, in Solid Supports and Catalysts in Organic Synthesis (Ed.: K. Smith), Ellis Harwood and PTR Prentice Hall, New York and London, 1992, Chapters 1, 3, and 5;
84. b) M. H. Ali, M. McDermott, Tetrahedron Lett. 2002, 43, 6271-6273;
85. c) S. Kotha, K. Mandal, A.C. Deb, S. Banerjee, Tetrahedron Lett. 2004, 45, 9603-9605;
86. d)N. Ahmed, H. Ali, J. E. van Lier, Tetrahedron Lett. 2005, 46, 253-256.
87. We have also observed that use of old catalyst in the RCM of compound 14a decreased the yield of the RCM product; see: reference [12].
88. M. Mori, N. Sakakibara, A. Kinoshita, J. Org. Chem. 1998, 63, 6082-6083.
89. Earlier reports on ethylene-promoted ring-closing enyne metathesis, see: a) T. Kitamura, M. Mori, Org. Lett. 2001, 3, 1161-1163;
90. b) A. Ruckert, D. Eisele, S. Blechert, Tetrahedron Lett. 2001, 42, 5245-5247;
91. c) N. Saito, Y. Sato, M. Mori, Org. Lett. 2002, 4, 803-805;
92. d) H. Guo, R. J. Madhushaw, F. M. Shen, R. S. Liu, Tetrahedron 2002, 58, 5627-5637;
93. e) M. E. Layton, C. A. Morales, M. D. Shair, J. Am. Chem. Soc. 2002, 124, 773-775;
94. f) D. Banti, M. North, Adv. Synth. Catal. 2002, 344, 694-704;
95. g) J. S. Clark, F. Elustondo, M. C. Kimber, Chem. Commun. 2004, 2470-2471;
96. h) E. C. Hansen, D. Lee, J. Am. Chem. Soc. 2004, 126, 15074-15080;
97. i) T. Kitamura, Y. Sato, M. Mori, Tetrahedron 2004, 60, 9649-9657;
98. j) C. A. Morales, M. E. Layton, M. D. Shair, Proc. Natl. Acad. Sci. USA 2004, 101, 12036-12041;
99. k) A. G. M. Barrett, A. J. Hennessy, R. L. Vezouet, P. A. Procopiou, P. W. Seale, S. Stefaniak, R. J. Upton, A. J. P. White, D. J. Williams, J. Org. Chem. 2004, 69, 1028-1037.
100. 1H NMR analysis.
101. Related examples of one-pot RCEM/cycloadditions see: a) J. Renaud, C.-D. Graf, L. Oberer, Angew. Chem. 2000, 112, 3231-3234;
102. Angew. Chem. Int. Ed. 2000, 39, 3101-3104;
103. b) D. Bentz, S. Laschat, Synthesis 2000, 1766-1773;
104. c) M. Moreno-Manas, R. Pleixats, A. Santamaria, Synlett 2001, 1784-1786.
105. Catalyst was added in multiple portions at different time intervals.
106. M. Mousseron, R. Jacquier, H. Christol, Bull. Soc. Chim. Fr. 1957, 346-356.
107. a) T. R. Hoye, M. A. Promo, Tetrahedron Lett. 1999, 40, 1429-1432;
108. b) M. K. Gurjar, P. Yakambram, Tetrahedron Lett. 2001, 42, 3633-3636;
109. c) S. S. Kinderman, J. H. van Maarseveen, H. E. Schoemaker, H. Hiemstra, P. J. T. Rutjes, Org. Lett. 2001, 3, 2045-2048;
110. d) D. C. Braddock, A. J. Wildsmith, Tetrahedron Lett. 2001, 42, 3239-3242;
111. e) C. Cadot, P. I. Dalko, J. Cossy, Tetrahedron Lett. 2002, 43, 1839-1841;
112. f) D. C. Braddock, A. Matsuno, Tetrahedron Lett. 2002, 43, 3305-3308;
113. g) A. E. Sutton, A. Benjamin, A. Seigal, D. F. Finnegan, M. L. Snapper, J. Am. Chem. Soc. 2002, 124, 13390-13391;
114. h) M. Arisawa, Y. Terada, M. Nakagawa, A. Nishida, Angew. Chem. 2002, 114, 4926-4928;
115. Angew. Chem. Int. Ed. 2002, 41, 4732-4734;
116. i) B. Alcaide, P. Almendros, Chem. Eur. J. 2003, 9, 1259-1262;
117. j) W. A. L. van Otterlo, E. L. Ngidi, C. B. de Koning, Tetrahedron Lett. 2003, 44, 6483-6486.
118. a) B. Schmidt, Eur. J. Org. Chem. 2003, 816-819;
119. b) B. Schmidt, Synlett 2004, 1541-1544.
120. For benzylic oxidation with PCC, see: a) R. Rathore, N. Saxena, S. Chandrasekaran, Synth. Commun. 1986, 16, 1493-1508;
121. b) E. J. Parish, S. Chitrakorn, T. Y. Wei, Synth. Commun. 1986, 16, 1371-1375.
122. a) F. C. Gozzo, S.A. Fernandes, D. C. Rodrigues, M. N. Eberlin, A. J. Marsaioli, J. Org. Chem. 2003, 68, 5493-5499;
123. b) A. S. R. Anjaneyulu, J. Chem. Soc. Perkin Trans. 1: 1990, 993-998.
124. N. Matsunaga, T. Kaku, A. Ojida, T. Tanaka, T. Hara, M. Yamaoka, M. Kusakab, A. Tasaka, Bioorg. Med. Chem. 2004, 12, 4313-4336.
125. J. Jaechon, K. Heean, L. Hyunsuk, C. Jaeyoung, M. Kazumi, K. Yoshitake, N. Masahiro, K. Myunghwa, N. Yoshikazu, PCT Int. Appl. WO 2001042186 (Chem. Abstr. 2001, 735, 19815].
126. a)J. Green, D. McHale, Chem. Ind. 1964, 1801-1802;
127. b) G. Bram, A. Loupy, J. Sansoulet, E Vaziri-Zand, Nouv. J. Chim. 1986, 10, 765-775.
128. W. A. L. van Otterlo, G. L. Morgans, L. G. Madeley, S. Kuzvidza, S. S. Moleele, N. Thornton, C. B. de Koning, Tetrahedron 2005, 61, 7746-7755.
129. L. Prajer-Janczewska, J. Wróblewski, Pol. J. Chem. 1980, 54, 1431-1437.
130. B. M. Trost, J. Xu, J. Am. Chem. Soc. 2005, 127, 2846-2847.
131. J. M. Cid, J. L. Romera, A. A. Trabanco, Tetrahedron Lett. 2004, 45, 1133-1136.
132. P. Cagniant, C. Charaux, Bull. Soc. Chim. Fr. 1966, 3249-3258.
133. a) V. K. Tandon, R. B. Chhor, G. K. Goswamy, Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem. 1998, 37B, 1027-1029;
134. b) K. V. Nikitin, N. P. Andryukhova, Can. J. Chem. 2004, 82, 571-578.