Scope and mechanism of direct indole and pyrrole couplings adjacent to carbonyl compounds: Total synthesis of acremoauxin A and oxazinin 3

Journal of the American Chemical Society

Volumn 129, Issue 42, 2007, Pages 12857-12869

  Richter, Jeremy M ^a   Whitefield, Brandon W ^a   Maimone, Thomas J ^a   Lin, David W ^a   Castroviejo, M Pilar ^a   Baran, Phil S ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL COMPOUNDS; CHEMOSELECTIVITY; SYNTHETIC PROBLEMS;

ELECTRON TRANSPORT PROPERTIES; FUNCTIONAL GROUPS; NEGATIVE IONS; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

NITROGEN COMPOUNDS;

ACREMOAUXIN A; AUXIN; CARBONYL DERIVATIVE; INDOLE DERIVATIVE; OXAZINE DERIVATIVE; OXAZININ 3; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; STEREOCHEMISTRY; STEREOSPECIFICITY; STRUCTURE ANALYSIS; SYNTHESIS;

CARBON; CHEMISTRY, ORGANIC; DIMERIZATION; ELECTRONS; INDOLES; KETOROLAC; MODELS, CHEMICAL; MOLECULAR CONFORMATION; MORPHOLINES; OXAZINES; OXYGEN; PHOSPHINES; PYRROLES; STEREOISOMERISM;

EID: 35548972055     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja074392m     Document Type: Article

References (156)

1. Suzuki, A.; Brown, H. C. Organic Syntheses Via Boranes, Vol. 3, Suzuki Coupling; Aldrich Chemical Company, Inc.: Milwaukee, WI, 2003.
2. For example, see: (a) Harrington, P. J.; Hegedus, L. S. J. Org. Chem. 1993, 49, 2657-2662.
3. (b) Harrington, P. J.; Hegedus, L. S.; McDaniel, K. F. J. Am. Chem. Soc. 1987, 109, 4335-4338.
4. For example, see: (a) Kozikowski, A. P.; Ma, D. Tetrahedron Lett. 1991, 32, 3317-3320.
5. (b) Kozikowski, A. P.; Ma, D.; Brewer, J.; Sun, S.; Costa, E.; Romeo, E.; Guidotti, A. J. Med. Chem. 1993, 36, 2908-2920.
6. (a) This reaction has extensive precedent, see: Itahara, T. J. Chem. Soc., Chem. Commun. 1981, 254-255.
7. (b) For additional examples, see: Li, J. J.; Gribble, G. W. Palladium in Heterocyclic Chemistry: A Guide for the Synthetic Chemist, 2nd ed.; Elsevier: San Diego, CA, 2007.
8. (c) For a microwave-mediated variant, see: Stuart, D. R.; Fagnou, K. Science 2007, 316, 1172-1175.
9. Bandini, M.; Melloni, A.; Tommasi, S.; Umani-Ronchi, A. Synlett 2005, 1199-1222.
10. Dyker, G. Handbook of C-H Transformations: Applications in Organic Synthesis;. Wiley-VCH: Weinheim, 2005; Vols. 1-2.
11. Baran, P. S.; Richter, J. M. J. Am. Chem. Soc. 2004, 126, 7450-7451.
12. Baran, P. S.; Richter, J. M.; Lin, D. W. Angew. Chem., Int. Ed. 2005, 44, 609-612.
13. (a) Baran, P. S.; Richter, J. M. J. Am. Chem. Soc. 2005, 127, 15394-15396.
14. (b) Baran, P. S.; Maimone, T. J.; Richter, J. M. Nature 2007, 446, 404-408.
15. For isolation see: (a) Moore, R. E.; Cheuk, C.; Yang, X.-Q. G.; Patterson, G. M. L.; Bonjouklian, R.; Smitka, T. A.; Mynderse, J. S.; Foster, R. S.; Jones, N. D.; Swartzendruber, J. K.; Deeter, J. B. J. Org. Chem. 1987, 52, 1036-1043.
16. (b) Stratmann, K.; Moore, R. E.; Bonjouklian, R.; Deeter, J. B.; Patterson, G. M. L.; Shaffer, S.; Smith, C. D.; Smitka, T. A. J. Am. Chem. Soc. 1994, 116, 9935-9942.
17. (c) Raveh, A.; Carmeli, S. J. Nat. Prod. 2007, 70, 196-201.
18. Fukuyama, T.; Chen, X. J. Am. Chem. Soc. 1994, 116, 3125-3126.
19. Vaillancourt, V.; Albizati, K. F. J. Am. Chem. Soc. 1993, 115, 3499-3502.
20. The coupling of the enol acetate of carvone with 3-bromo-N-TIPS- indole has been attempted using Albizati's conditions, and none of the desired product was obtained.
21. Barton, D. H. R.; Deflorin, A. M.; Edwards, O. E. J. Chem. Soc. 1956, 530-534.
22. Nicolaou, K. C.; Snyder, S. A. Angew. Chem., Int. Ed. 2005, 44, 1012-1044.
23. Anslyn, E. V.; Doughtery, D. A. Modern Physical Organic Chemistry; University Science Books: Sausalito, CA, 2006; pp 445-451.
24. Ivanoff, D.; Spassoff, A. Bull. Soc. Chim. Fr., Mem. 1935, 2, 76-78.
25. (a) Renaud, P.; Fox, M. A. J. Org. Chem. 1988, 53, 3745-3752.
26. (b) Chung, S. K.; Dunn, L. B., Jr. J. Org. Chem. 1983, 48, 1125-1127.
27. (c) Porter, N. A.; Jill, Q. S.; Harp, J. J.; Rosenstein, I. J.; McPhail, A. T. Tetrahedron Lett. 1993, 34, 4457-4460.
28. (d) Cohen, T.; McNamara, K.; Kuzemko, M. A.; Ramig, K.; Landi, J. J., Jr.; Dong, Y. Tetrahedron. 1993, 49, 7931-7942.
29. Kauffmann, T.; Beissner, G.; Berg, H.; Köppelmann, E.; Legier, J.; Schönfelder, M. Angew. Chem., Int. Ed. Engl. 1968, 7, 540-541.
30. Rathke, M. W.; Lindert, A. J. Am. Chem. Soc. 1971, 93, 4605-4606.
31. (a) Ito, Y.; Konoike, T.; Saegusa, T. J. Am. Chem. Soc. 1975, 97, 2912-2914.
32. (b) Ito, Y.; Konoike, T.; Harada, T.; Saegusa, T. J. Am. Chem. Soc. 1977, 99, 1487-1493.
33. (a) Kauffman, T.; Beissner, G.; Köppelmann, E.; Kuhlmann, D.; Schott, A.; Schrecken, H. Angew. Chem., Int. Ed. Engl. 1968, 7, 131-132.
34. (b) Kobayashi, Y.; Taguchi, T.; Tokuno, E. Tetrahedron Lett. 1977, 18, 3741-3742.
35. (c) Paquette, L. A.; Snow, R. A.; Muthard J. L.; Cynkowski, T. J. Am. Chem. Soc. 1978, 100, 1600-1602.
36. (d) Kobayashi, Y.; Taguchi, T.; Morikawa, T. Tetrahedron Lett. 1978, 19, 3555-3556.
37. (e) Paquette, L. A.; Snow, R. A.; Muthard, J. L.; Cynkowski, T. J. Am. Chem. Soc. 1979, 101, 6991-6996.
38. (f) Kobayashi, Y.; Taguchi, T.; Morikawa, T.; Tokuno, E.; Sekiguchi, S. Chem. Pharm. Bull. 1980, 28, 262-267.
39. (g) Babler, J. H.; Sarussi, S. J. J. Org. Chem. 1987, 52, 3462-3464.
40. (h) Quermann, R.; Maletz, R.; Schäfer, H. J. Liebigs Ann. Chem. 1993, 1219-1223.
41. (i) Studer, A.; Hintermann, T.; Seebach, D. Helv. Chim. Acta 1995, 78, 1185-1206.
42. (a) Frazier, R. H., Jr.; Harlow, R. L. J. Org. Chem. 1980, 45, 5408-5411.
43. (b) Poupart, M.-A.; Paquette, L. A. Tetrahedron Lett. 1988, 29, 269-272.
44. (c) Paquette, L. A.; Bzowej, E. I.; Branan, B. M.; Stanton, K. J. J. Org. Chem. 1995, 60, 7277-7283.
45. (d) Langer, T.; Illich, M.; Helmchen, G. Synlett. 1996, 1137-1139.
46. (e) Schmittel, M.; Söllner, R. Chem. Ber./Recl. 1997, 130, 771-777.
47. (f) Jahn, U. J. Org. Chem. 1998, 63, 7130-7131.
48. (g) Nguyen, P. Q.; Schäfer, H. J. Org. Lett. 2001, 3, 2993-2995.
49. (a) Beroza, M.; Schechter, M. S. J. Am. Chem. Soc. 1956, 78, 1242-1247.
50. (b) Mosby, W. L. J. Chem. Soc. 1957, 3997-4003.
51. (c) Charles, R. G. Org. Synth. 1959, 39, 61-62.
52. (d) Brocksom, T. J.; Petragnani, N.; Rodrigues, H.; Teixeira, L. S. Synthesis 1975, 396-397.
53. (e) Hampton, K. G.; Christie, J. J. J. Org. Chem. 1975, 40, 3887-3889.
54. (f) Tamaru, Y.; Harada, T.; Yoshida, Z.-i. J. Am. Chem. Soc. 1978, 100, 1923-1925.
55. (g) Pelter, A.; Ward, R. S.; Watson, D. J.; Jack, I. R. J. Chem. Soc., Perkin Trans. 1 1982, 183-190.
56. (h) Shatzmiller, S.; Lidor, R. Synthesis 1983, 590-593.
57. (i) Belletire, J. L.; Spletzer, E. G.; Pinhas, A. R. Tetrahedron Lett. 1984, 25, 5969-5972.
58. (j) Belletire, J. L.; Spletzer, E. G. Tetrahedron Lett. 1986, 27, 131-134.
59. (k) Belletire, J. L.; Spletzer, E. G. Synth. Commun. 1987, 17, 1701-1707.
60. (l) Drewes, S. E.; Hogan, C. J.; Kaye, P. T.; Roos, G. H. P. J. Chem. Soc., Perkin Trans. 1 1989, 1585-1591.
61. (m) Langer, T.; Illich, M.; Helmchen, G. Tetrahedron Lett. 1995, 36, 4409-4412.
62. (n) Wu, A.; Zhao, Y.; Chen, N.; Pan, X. Synth. Commun. 1997, 27, 331-336.
63. (o) Alvarez-Ibarra, C.; Csáky, A. G.; Colmenero, B.; Quiroga, M. L. J. Org. Chem. 1997, 62, 2478-2482.
64. Kawabata, T.; Sumi, K.; Hiyama, T. J. Am. Chem. Soc. 1989, 111, 6843-6845.
65. (a) Seveno, A.; Morel, G.; Foucaud, A.; Marchand, E. Tetrahedron Lett. 1977, 18, 3349-3352.
66. (b) Yan, J.; Zhong, L.-R.; Chen, Z.-C. J. Org. Chem. 1991, 56, 459-461.
67. (c) Kim, J. W.; Lee, J.-J.; Lee, S.-H.; Ahn, K.-H. Synth. Commun. 1998, 28, 1287-1292.
68. (d) Kise, N.; Ueda, T.; Kumada, K.; Terao, Y.; Ueda, N. J. Org. Chem. 2000, 65, 464-468.
69. Aurell, M. J.; Gil, S.; Tortajada, A.; Mestres, R.; García-Raso, A. Tetrahedron Lett. 1988, 29, 6181-6182.
70. (a) Ojima, I.; Brandstadter, S. M.; Donovan, R. J. Chem. Lett. 1992, 1591-1594.
71. (b) Kise, N.; Tokioka, K.; Aoyama, Y.; Matsumura, Y. J. Org. Chem. 1995, 60, 1100-1101.
72. (c) Matsumura, Y.; Nishimura, M.; Hiu, H.; Watanabe, M.; Kise, N. J. Org. Chem. 1996, 61, 2809-2812.
73. (d) Kise, N.; Kumada, K.; Terao, Y.; Ueda, N. Tetrahedron. 1998, 54, 2697-2708.
74. (e) Csáky, A. G.; Mula, M. B.; Mba, M.; Plumet, J. Tetrahedron: Asymmetry 2002, 13, 753-757.
75. Kaiser, E. M. J. Am. Chem. Soc. 1967, 89, 3659-3660.
76. (a) Okubo, T.; Tsutsumi, S. Bull. Chem. Soc. Jpn. 1964, 37, 1794-1797.
77. (b) Brettle, R.; Parkin, J. G. J. Chem. Soc. C 1967, 1352-1355.
78. (c) Brettle, R.; Parkin, J. G.; Seddon, D. J. Chem. Soc. C 1970, 1317-1320.
79. (d) VandenBorn, H. W.; Evans, D. H. J. Am. Chem. Soc. 1974, 96, 4296-4301.
80. (e) Tokuda, M.; Shigei, T.; Itoh, M. Chem. Lett. 1975, 621-624.
81. (f) Peek, R.; Streukens, M.; Thomas, H. G.; Vanderfuhr, A.; Wellen, U. Chem. Ber. 1994, 127, 1257-1262.
82. (a) Kofron, W. G.; Hauser, C. R. J. Org. Chem. 1970, 35, 2085-2086.
83. (b) Enders, D.; Müller, P.; Klein, D. Synlett 1998, 43-44.
84. Kise, N.; Fujimoto, A.; Ueda, N. Tetrahedron: Asymmetry 2002, 13, 1845-1847.
85. Belletire, J. L.; Spletzer, E. G. Synth. Commun. 1986, 16, 575-584.
86. Maryanoff, C. A.; Maryanoff, B. E.; Tang, R.; Mislow, K. J. Am. Chem. Soc. 1973, 95, 5839.
87. Ishikawa, H.; Takayama, H.; Aimi, N. Tetrahedron Lett. 2002, 43, 5637-5639.
88. For reviews that are completely or partially devoted to oxidative enolate coupling, see: (a) Weinberg, N. L.; Weinberg, H. R. Chem. Rev. 1968, 68, 449-523.
89. (b) Kauffmann, T. Angew. Chem., Int. Ed. Engl. 1974, 13, 291-356.
90. (c) Csáky, A. G.; Plumet, J. Chem. Soc. Rev. 2001, 30, 313-320.
91. (d) Baran, P. S.; Ainbhaikar, N. A.; Guerrero, C. A.; Hafensteiner, B. D.; Lin, D. W.; Richter, J. M. Arkivoc. 2006, vii, 310-325.
92. (a) Belletire, J. L.; Fremont, S. L. Tetrahedron Lett. 1986, 27, 127-130.
93. (b) Belletire, J. L.; Fry, D. F. J. Org. Chem. 1987, 52, 2549-2555.
94. (c) Belletire, J. L.; Fry, D. F. J. Org. Chem. 1988, 53, 4724-4729.
95. (d) Ramig, K.; Kuzeinko, M. A.; McNamara, K.; Cohen, T. J. Org. Chem. 1992, 57, 1968-1969.
96. (e) Paquette, L. A.; Poupart, M.-A. J. Org. Chem. 1993, 58, 4245-4253.
97. Narasaka, K.; Okauchi, T.; Tanaka, K.; Murakami, M. Chem. Lett. 1992, 2099-2102.
98. For a catalytic version, see: (a) Sibi, M. P.; Hasegawa, M. J. Am. Chem. Soc. 2007, 129, 4124-4125.
99. (b) Beeson, T. D.; Mastracchio, A.; Hong, J.-B.; Ashton, K.; MacMillan, D. W. C. Science 2007, 316, 582-585.
100. (c) Jang, H.-Y.; Hong, J.-B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2007, 129, 7004-7005.
101. Dessau, R. M.; Heiba, E. I. J. Org. Chem. 1974, 39, 3457-3459.
102. Ito, Y.; Konoike, T.; Saegusa, T. J. Am. Chem. Soc. 1975, 97, 649-651.
103. (a) Inaba, S.-i.; Ojima, I. Tetrahedron Lett. 1977, 18, 2009-2012.
104. (b) Hirai, K.; Ojima, I. Tetrahedron Lett. 1983, 24, 785-788.
105. (c) Totten, G. E.; Wenke, G.; Rhodes, Y. E. Synth. Commun. 1985, 15, 291-300.
106. (a) Baciocchi, E.; Civitarese, G.; Ruzziconi, R. Tetrahedron Lett. 1987, 28, 5357-5360.
107. (b) Baciocchi, E.; Casu, A.; Ruzziconi, R. Tetrahedron Lett. 1989, 30, 3707-3710.
108. (c) Paolobelli, A. B.; Latini, D.; Ruzziconi, R. Tetrahedron Lett. 1993, 34, 721-724.
109. Moeller, K. D.; Tinao, L. V. J. Am. Chem. Soc. 1992, 114, 1033-1041.
110. (a) Fujii, T.; Hirao, T.; Ohshiro, Y. Tetrahedron Lett. 1992, 33, 5823-5826.
111. (b) Ryter, K.; Livinghouse, T. J. Am. Chem. Soc. 1998, 120, 2658-2659.
112. Schmittel, M.; Burghart, A.; Malisch, W.; Reising, J.; Söllner, R. J. Org. Chem. 1998, 63, 396-400.
113. (a) Whitehead, C. R.; Sessions, E. H.; Ghiviriga, I.; Wright, D. L. Org. Lett. 2002, 4, 3763-3765.
114. (b) Mihelcic, J.; Moeller, K. D. J. Am. Chem. Soc. 2004, 126, 9106-9111.
115. (c) Miller, A. K.; Hughes, C. C.; Kennedy-Smith, J. J.; Gradl, S. N.; Trauner, D. J. Am. Chem. Soc. 2006, 128, 17057-17062.
116. (a) Itahara, T.; Ikeda, M.; Sakakibara, T. J. Chem. Soc., Perkin Trans. 1 1983, 1361-1363.
117. (b) Itahara, T.; Kawasaki, K.; Ouseto, F. Synthesis 1984, 236-237.
118. (c) For additional references, see ref 4b, pp 90-96.
119. The experimental procedure involved immediately transferring the flask containing the reaction mixture and the oxidant at -78°C into a bath of the desired temperature (i.e., -20°C in this entry) and allowing the reaction to stir for 10 min before quenching.
120. It was found that opening the reaction flask to the ambient atmosphere for the time required for addition was not detrimental to the reaction yield. Comparison studies were performed in which the reaction was performed under meticulous Schlenk technique (degassed, rigorously dry, and the oxidant was added as a solution in THF) and an identical yield of the product was obtained.
121. See Supporting Information for a detailed general procedure.
122. Several of the adducts listed in Table 2 would be difficult or nearly impossible to obtain so quickly in any other fashion.
123. Sassa, T.; Yoshida, N.; Haruki, E. Agric. Biol. Chem. 1989, 53, 3105-3107.
124. Yoshida, N.; Sassa, Y. Agric. Biol. Chem. 1990, 54, 2681-2683.
125. See Supporting Information for preparation.
126. Isolation; Ciminiello, P.; Dell'Aversano, C.; Fattorusso, E.; Forino, M.; Magno, S.; Ianaro, A.; Di Rosa, M. Eur. J. Org. Chem. 2001, 49-53.
127. For a previous synthesis, see: Couladouros, E. A.; Moutsos, V. I.; Pitsinos, E. N. Tetrahedron Lett. 2004, 45, 7779-7781.
128. It should be noted that enolate alkylation is expected to proceed with this configuration, but it was unknown if a similar stereochemical outcome would predominate with the indole coupling reaction.
129. See Supporting Information for preparation.
130. House, H. O.; Umen, M. J. J. Org. Chem. 1973, 38, 1000-1003.
131. Baran, P. S.; DeMartino, M. P. Angew. Chem., Int. Ed. 2006, 45, 7083-7086.
132. Joule, J. A.; Mills, K. Heterocyclic Chemistry, 4th ed.; Blackwell Science: Maiden, MA, 2004.
133. See Supporting Information for a detailed general procedure.
134. (a) Closs, G. L.; Schwartz, G. M. J. Org. Chem. 1961, 26, 2609.
135. (b) Jones, R. L.; Rees, C. W. J. Chem. Soc. C 1969, 2249-2251.
136. Chen, Q.; Wang, T.; Zhang, Y.; Wang, Q.; Ma, J. Synth. Commun. 2002, 32, 1031-1040.
137. Denmark, S. E.; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479-3486.
138. (a) Muchowski, J. M. Adv. Med. Chem. 1992, 1, 109-135.
139. (b) Harrington, P. J.; Khatri, H. N.; Schloemer, G. C. U.S. Patent 6197976, 2001, and references therein.
140. Guzmán, A.; Yuste, F.; Toscano, R. A.; Young, J. M.; Van Horn, A. R.; Muchowski, J. M. J. Med. Chem. 1986, 29, 589-591.
141. Ketorolac is still marketed as a racemate, despite the fact that one enantiomer is known to be more active than the other.
142. Li, J.-H.; Snyder, J. K. J. Org. Chem. 1993, 58, 516-519.
143. (a) Jahn, U.; Hartmann, P. Chem. Commun. 1998, 209-210.
144. (b) Jahn, U. J. Org. Chem. 1998, 63, 7130-7131.
145. (c) Jahn, U.; Muller, M.; Aussieker, S. J. Am. Chem. Soc. 2000, 122, 5212-5213.
146. (d) Jahn, U.; Hartmann, P. J. Chem. Soc., Perkin Trans. 1 2001, 2277-2282.
147. (e) Jahn, U.; Hartmann, P.; Dix, I.; Jones, P. G. Eur. J. Org. Chem. 2001, 3333-3355.
148. (f) Jahn, U.; Hartmann, P.; Dix, I.; Jones, P. G. Eur. J. Org. Chem. 2002, 718-735.
149. Benzoylation effectively removes electron density from and, thereby, stabilizes the pyrrole.
150. Muchowski, J. M.; et. al. J. Med. Chem. 1985, 28, 1037-1049.
151. Hasegawa, T.; Yamamoto, H. Synlett 1998, 882-884.
152. r = mmol starting carvone placed in the reaction.
153. Swain, C. G.; Lupton, E. C., Jr. J. Am. Chem. Soc. 1968, 90, 4328-4337.
154. (a) Baran, P. S.; Guerrero, C. A.; Ambhaikar, N. A.; Hafensteiner, B. D. Angew. Chem., Int. Ed. 2005, 44, 606-609.
155. (b) Baran, P. S.; Guerrero, C. A.; Hafensteiner, B. D.; Ambhaikar, N. A. Angew. Chem., Int. Ed. 2005, 44, 3892-3895.
156. (c) Baran, P. S.; Hafensteiner, B. D.; Ambhaikar, N. A.; Guerrero, C. A.; Gallagher, J. D. J. Am. Chem. Soc. 2006, 128, 8678-8693.