Stereocontrolled total syntheses of isodomoic acids G and H via a unified strategy

Journal of Organic Chemistry

Volumn 76, Issue 1, 2011, Pages 201-215

  Denmark, Scott E ^a   Liu, Jack Hung Chang ^a   Muhuhi, Joseck M ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL; CROSS COUPLING REACTIONS; CYCLIZATION PRODUCTS; DIASTEREOSELECTIVE; PYRROLIDINES; RHODIUM-CATALYZED; SIDE-CHAIN; SILICON-BASED; TARGET COMPOUND; TARGET MOLECULE; TOTAL SYNTHESIS;

REACTION INTERMEDIATES; RHODIUM; SILICON COMPOUNDS; SYNTHESIS (CHEMICAL);

CYCLIZATION;

ALKENYL GROUP; GLYCINE; ISODOMOIC ACID G; ISODOMOIC ACID H; PYRROLIDINE DERIVATIVE; RHODIUM; SILICON; SILICON DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CARBONYLATION; CROSS COUPLING REACTION; CYCLIZATION; DEPROTECTION REACTION; DIASTEREOISOMER; IODINATION; NONHUMAN; STEREOCHEMISTRY; SYNTHESIS;

ALKENES; CROSS-LINKING REAGENTS; CYCLIZATION; HEPTANOIC ACIDS; MOLECULAR STRUCTURE; SILICON; STEREOISOMERISM;

EID: 78650915590     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101790z     Document Type: Article

References (150)

1. For comprehensive reviews, see: Parsons, A. F. Tetrahedron 1996, 52, 4149-4174
2. Moloney, M. G. Nat. Prod. Rep. 1998, 15, 205-209
3. Moloney, M. G. Nat. Prod. Rep. 1999, 16, 485-498
4. Clayden, J.; Read, B.; Hebditch, K. R. Tetrahedron 2005, 61, 5713-5724
5. Murakami, S.; Takemoto, T.; Shimizu, Z. J. Pharm. Soc. Jpn. 1953, 73, 1026-1028
6. Takemoto, T.; Daigo, K. Chem. Pharm. Bull. 1958, 6, 578-580
7. Maeda, M.; Kodama, T.; Tanaka, T.; Yoshizumi, H.; Takemoto, T.; Nomoto, K.; Fujita, T. Chem. Pharm. Bull. 1986, 34, 4892-4895
8. Maeda, M.; Kodama, T.; Tanaka, T.; Yoshizumi, H.; Takemoto, T.; Nomoto, K.; Fujita, T. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1985, 27, 616-623
9. Maeda, M.; Kodama, T.; Tanaka, T.; Yoshizumi, H.; Takemoto, T.; Nomoto, K.; Fujita, T. Tetrahedron Lett. 1987, 28, 633-636
10. Wright, J. L. C.; Boyd, R. K.; De Freitas, A. S. W.; Falk, M.; Foxall, R. A.; Jamieson, W. D.; Laycock, M. V.; McCulloch, A. W.; McInnes, A. G.; Odense, P.; Pathak, V. P.; Quilliam, M. A.; Ragan, M. A.; Sim, P. G.; Thibault, P.; Walter, J. A.; Gilgan, M.; Richard, D. J. A.; Dewar, D. Can. J. Chem. 1989, 67, 481-490
11. Walter, J. A.; Falk, M.; Wright, J. L. C. Can. J. Chem. 1993, 72, 430-436
12. Walter, J. A.; Falk, M.; McInnes, A. G.; Wright, J. L. C. Can. J. Chem. 1990, 68, 22-25
13. Bates, S. S.; Bird, C. J.; De Freitas, A. S. W.; Foxall, R.; Gilgan, M.; Hanic, L. A.; Johnson, G. R.; McCulloch, A. W.; Odense, P. Can. J. Fish. Aquat. Sci. 1989, 46, 1203-1215
14. Zaman, L.; Arakawa, O.; Shimosu, A.; Onoue, Y.; Nishio, S.; Shida, Y.; Noguchi, T. Toxicon 1997, 35, 205-212
15. Ni, Y.; Amarasinghe, K. D.; Ksebati, B.; Montgomery, J. Org. Lett. 2003, 5, 3771-3773
16. Ni, Y.; Kassab, R. M.; Chevliakov, M. V.; Montgomery, J. J. Am. Chem. Soc. 2009, 131, 17714-17718
17. Kainic Acid as a Tool in Neurobiology; McGeer, E. G.; Olney, J. W.; McGeer, P. L., Eds.; Raven: New York, 1978.
18. Excitatory Amino Acids; Simon, R. P., Ed.; Thieme Medical: New York, 1992.
19. Excitatory Amino Acids and Synaptic Transmission; Wheal, H. V.; Thomson, A. M., Eds.; Academic: London, 1991.
20. Waring, R. H.; Steventon, G. B.; Mitchell, S. C. Molecules of Death; Imperial College: London, 2002.
21. Johnson, G. A. R.; Curtis, D. R.; Davis, J.; McCulloch, R. M. Nature 1974, 248, 804-805
22. Monaghan, D. T.; Bridges, R. J.; Cotman, C. W. Annu. Rev. Pharmacol. Toxicol. 1989, 29, 365-402
23. Hansen, J. J.; Krogsgaard-Larsen, P. Med. Res. Rev. 1990, 10, 55-94
24. Young, A. B.; Fagg, G. E. Trends Pharmacol. Sci. 1990, 11, 126-133
25. Ishida, M.; Shinozaki, H. Br. J. Pharmacol. 1991, 104, 873-878
26. Sommer, B.; Seeburg, P. H. Trends Pharmacol. Sci. 1992, 13, 291-296
27. Seeberg, P. H. Trends Neurosci. 1993, 16, 359-365
28. Hollmann, M.; Heinemann, S. Annu. Rev. Neurosci. 1994, 17, 31-108
29. Hashimoto, K.; Ohfune, Y.; Shirahama, H. Tetrahedron Lett. 1995, 36, 6235-6238
30. Tanaka, T.; Maeda, M.; Toshizumi, H.; Nomoto, K. Japanese patent 60188366, 1985.
31. Nomoto, K.; Takemoto, T.; Maeda, M.; In, Y.; Doi, M.; Inoue, M.; Ishida, T. Biochem. Biophys. Res. Commun. 1992, 187, 325-331
32. Tremblay, J.-F. Chem. Eng. News 2000, 78 (1) 14-15
33. Tremblay, J.-F. Chem. Eng. News 2000, 78 (10) 31
34. Tremblay, J.-F. Chem. Eng. News 2001, 79 (5) 19
35. Oppolzer, W.; Thirring, K. J. Am. Chem. Soc. 1982, 104, 4978-4979
36. Ohfune, Y.; Tomita, M. J. Am. Chem. Soc. 1982, 104, 3511-3513
37. Clayden, J.; Knowles, F. E.; Baldwin, I. R. J. Am. Chem. Soc. 2005, 127, 2412-2413
38. Denmark, S. E.; Liu, J. H.-C.; Muhuhi, J. M. J. Am. Chem. Soc. 2009, 131, 14188-14189
39. Denmark, S. E.; Liu, J. H.-C. J. Am. Chem. Soc. 2007, 129, 3737-3744
40. Ojima, I.; Vu, A. T.; Lee, S.-Y.; McCullagh, J. V.; Moralee, A. C.; Fujiwara, M.; Hoang, T. M. J. Am. Chem. Soc. 2002, 124, 9164-9174
41. Maerten, E.; Delerue, H.; Queste, M.; Nowicki, A.; Suisse, I.; Agbossou-Niedercorn, F. Tetrahedron: Asymmetry 2004, 15, 3019-3022
42. For reviews on silylcarbocyclization, see: Tamao, K.; Kobayashi, K.; Ito, Y. Synlett 1991, 539-546
43. Ojima, I.; Moralee, A. C.; Vassar, V. C. Top. Catal. 2002, 19, 89-99
44. Widenhoefer, R. A. Acc. Chem. Res. 2003, 35, 905-913
45. Varchi, G.; Ojima, I. Curr. Org. Chem. 2006, 10, 1341-1362
46. Widenhoefer, R. A.; Bender, C. F. In Comprehensive Organometallic Chemistry III
47. Crabtree, R. S.; Mingos, D. M. P., Eds.; Elsevier: Amsterdam; 2007; Chapter 11.11.
48. For reviews on silicon-based coupling, see: Hatanaka, Y.; Hiyama, T. J. Synth. Org. Chem. Jpn. 1990, 48, 834-843
49. Hatanaka, Y.; Hiyama, T. Synlett 1991, 845-853
50. Hiyama, T.; Hatanaka, Y. Pure. Appl. Chem. 1994, 66, 1471-1478
51. Hiyama, T. In Metal Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 10.
52. DeShong, P.; Handy, C. J.; Mowery, M. E. Pure Appl. Chem. 2000, 72, 1655-1658
53. Hiyama, T.; Shirakawa, E. Top. Curr. Chem. 2002, 219, 62-85
54. Denmark, S. E.; Sweis, R. F. Chem. Pharm. Bull. 2002, 50, 1531-1541
55. Denmark, S. E.; Sweis, R. F. Acc. Chem. Res. 2002, 35, 835-846
56. Denmark, S. E.; Ober, M. H. Aldrichim. Acta 2003, 36, 57-85
57. Denmark, S. E.; Sweis, R. F. In Metal Catalyzed Cross-Coupling Reactions: Second, Completely Revised and Enlarged Edition; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004; Chapter 4.
58. Tsuji, J. Palladium Reagents and Catalysts: New Perspectives for the 21st Century; Wiley: Wessex, England, 2004; pp 339 - 348.
59. Nakao, Y.; Sahoo, A. K.; Imanaka, H.; Yada, A.; Hiyama, T. Pure Appl. Chem. 2006, 78, 435-440
60. Denmark, S. E.; Baird, J. D. Chem.-Eur. J. 2006, 12, 4953-4963
61. Denmark, S. E.; Regens, C. S. Acc. Chem. Res. 2008, 41, 1486-1499
62. Denmark, S. E. J. Org. Chem. 2009, 74, 2915-3236
63. Denmark, S. E.; Liu, J. H.-C. Angew. Chem., Int. Ed. 2010, 49, 2978-2986
64. Denmark, S. E.; Pan, W. J. Organomet. Chem. 2002, 653, 98-104
65. Evans, D. A.; Ennis, M. D.; Mathre, D. J. J. Am. Chem. Soc. 1982, 104, 1737-1739
66. Lewis, N.; McKillop, A.; Taylor, R. J. K.; Watson, R. J. Synth. Commun. 1995, 25, 561-568
67. For a review of reductive amination, see: Baxter, E. W.; Reitz, A. B. Org. React. 2002, 59, 1-57
68. Grigg, R; Cooper, D. M.; Holloway, S.; McDonald, S.; Millington, E.; Sarker, M. A. B. Tetrahedron 2005, 61, 8677-8685
69. Afzali-Ardakani, A.; Rapoport, H. J. Org. Chem. 1980, 45, 4817-4820
70. Carrasco, M.; Jones, R. J.; Kamel, S.; Rapoport, H.; Truong, T. Organic Syntheses; Wiley: New York, 1998; Vol. 9, pp 63 - 66.
71. Krebs, A.; Ludwig, V.; Pfizer, J.; Dürner, G.; Göbel, M. W. Chem.-Eur. J. 2004, 10, 544-553
72. Kitamura, T.; Sato, Y.; Mori, M. Tetrahedron 2004, 60, 9649-9657
73. Bartley, D. B.; Coward, J. K. J. Org. Chem. 2005, 70, 6757-6774
74. Günter, M.; Gais, H.-J. J. Org. Chem. 2003, 68, 8037-8041
75. Brummond, K. M.; Mitasev, B. Org. Lett. 2004, 6, 2245-2248
76. Angle, S. R.; Henry, R. M. J. Org. Chem. 1998, 63, 7490-7497
77. Mastalerz, H.; Gavai, A. V.; Fink, B.; Struzynski, C.; Tarrant, J.; Vite, G. D.; Wong, T. W.; Zhang, G.; Vyas, D. M. Can. J. Chem. 2006, 84, 528-533
78. Tiecco, M.; Testaferri, L.; Temperini, A.; Terlizzi, R.; Bagnoli, L.; Marini, F.; Santi, C. Org. Biomol. Chem. 2007, 5, 3510-3519
79. Hoffman, T.; Waibel, R.; Gmeiner, P. J. Org. Chem. 2003, 68, 62-69
80. Li, L.-S.; Rader, C.; Matsushita, M.; Das, S.; Barbas, C. F., III; Lerner, R. A.; Sinha, S. J. Med. Chem. 2004, 47, 5630-5640
81. Vallee, E.; Loemba, F.; Etheve-Quelquejeu, M.; Valéry, J.-M. Tetrahedron Lett. 2006, 47, 2191-2195
82. Pellicciari, R.; Natalini, B.; Marinozzi, M. Synth. Commun. 1988, 18, 1715-1721
83. Bartley, D. M.; Coward, J. K. J. Org. Chem. 2005, 70, 6757-6774
84. Feng, Y.; Coward, J. K. J. Med. Chem. 2006, 49, 770-788
85. Bajgrowicz, J. A.; El Hallaoui, A.; Jacquier, R.; Pigière, C.; Viallefont, P. Tetrahedron Lett. 1984, 25, 2231-2234
86. Baldwin, J. E.; North, M.; Flinn, A. Tetrahedron 1988, 44, 637-642
87. Koch, T.; Buchardt, O. Synthesis 1993, 1065-1067
88. Wang, M.-C.; Zhang, Q.-J.; Zhao, W.-X.; Wang, X.-D.; Ding, X.; Jing, T.-T.; Song, M.-P. J. Org. Chem. 2008, 73, 168-176
89. Kricheldorf, H. R. Angew. Chem., Int. Ed. Engl. 1979, 18, 689-690
90. Kolb, M.; Barth, J. Synth. Commun. 1981, 11, 763-767
91. Schmidt, A. H.; Russ, M. Chem. Ber. 1981, 114, 1099-1110
92. Larchevêque, M.; Henrot, S. Tetrahedron Lett. 1987, 28, 1781-1782
93. Labrouillère, M.; Le Roux, C.; Ousaid, A.; Gaspard-Iloughmane, H.; Dubac, J. Bull. Soc. Chim. Fr. 1995, 32, 511-530
94. Barton, D. H. R.; Chrich, D.; Hervé, Y.; Potier, P.; Thierry, J. Tetrahedron 1985, 41, 4347-4357
95. Pedersen, M. L.; Berkowitz, D. B. J. Org. Chem. 1993, 58, 6966-6975
96. Itaya, T.; Shimizu, S.; Nakagawa, S.; Morisue, M. Chem. Pharm. Bull. 1994, 42, 1927-1930
97. Berkowitz, D. B.; Smith, M. K. Synthesis 1996, 39-41
98. Siebum, A. H. G.; Woo, W. S.; Raap, J.; Lugtenburg, J. Eur. J. Org. Chem. 2004, 2905-2913
99. Trost, B. M.; Machacek, M. R.; Ball, Z. T. Org. Lett. 2003, 5, 1895-1898
100. Trost, B. M.; Ball, Z. T. J. Am. Chem. Soc. 2005, 127, 17644-17655
101. Denmark, S. E.; Tymonko, S. A. J. Am. Chem. Soc. 2005, 127, 8004-8005
102. Trost, B. M.; Machacek, M. R.; Faulk, B. D. J. Am. Chem. Soc. 2006, 128, 6745-6754
103. For a review on Pinnick oxidation, see: Raach, A.; Reiser, O. J. Prakt. Chem. 2000, 342, 605-608
104. For the synthesis of 3, see the Supporting Information.
105. Zakarian, A.; Batch, A.; Holton, R. A. J. Am. Chem. Soc. 2003, 125, 7822-7824
106. Fuwa, H.; Ebine, M.; Sasaki, M. J. Am. Chem. Soc. 2006, 128, 9648-9650
107. Fuwa, H.; Ebine, M.; Bourdelais, A. J.; Baden, D. G.; Sasaki, M. J. Am. Chem. Soc. 2006, 128, 16989-16999
108. Lu, C.-D.; Zakarian, A. Org. Lett. 2007, 9, 3161-3163
109. The Pinnick oxidation of 25 and the subsequent methylation following previously developed procedures proceeded well, but the separation of the diastereomers proved difficult at every stage along this route.
110. See the Supporting Information for full details of the structural assignment.
111. Murphy, P. J.; Spencer, J. L.; Proctor, G. Tetrahedron Lett. 1990, 31, 1051-1054
112. Kahle, K.; Murphy, P. J.; Scott, J.; Tamagni, R. J. Chem. Soc., Perkin Trans. 1 1997, 997-999
113. Arsenyan, P.; Oberte, K.; Rubina, K.; Belyakov, S. Tetrahedron Lett. 2005, 46, 1001-1003
114. Lowe, J. T.; Youngsaye, W.; Panek, J. S. J. Org. Chem. 2006, 71, 3639-3642
115. Su, Q.; Dakin, L. A.; Panek, J. S. J. Org. Chem. 2007, 72, 2-24
116. Kanomata, N.; Maruyama, S.; Tomono, K.; Anada, S. Tetrahedron Lett. 2003, 44, 3599-3603
117. Fairlamb, I. J. S.; Kapdi, A. R.; Lee, A. F. Org. Lett. 2004, 6, 4435-4438
118. Landini, D.; Maia, A.; Rampoldi, A. J. Org. Chem. 1989, 54, 328-332
119. Albanese, D.; Ladini, D.; Penso, M. J. Org. Chem. 1998, 63, 9587-9589
120. The structures of hydrated tetraalkylammonium ions have been the subject of careful investigation for many years. A continuum of structures has been identified (depending upon ion structure and hydration level) that ranges from pure anions clathrates through framework structures through hydrogen bonded networks and finally to discrete polyhedral cluster anions; see: Jeffrey, G. A.; Mak, T. C. W. Science 1965, 149, 178-179
121. McLean, W. J.; Jeffrey, G. A. J. Chem. Phys. 1967, 47, 414-417
122. Gennick, I.; Harmon, K. M.; Potvin, M. M. Inorg. Chem. 1977, 16, 2033-2040
123. Yoo, S.-E.; Lee, S.-H.; Jeong, N.; Cho, I. Tetrahedron Lett. 1993, 34, 3435-3438
124. Yoo, S.-E.; Lee, S. H. J. Org. Chem. 1994, 59, 6968-6972
125. Miyata, O.; Ozawa, Y.; Nonmiya, I.; Naito, T. Synlett 1997, 275-276
126. Scott, M. E.; Lautens, M. Org. Lett. 2005, 7, 3045-3047
127. Pyne, S. G.; Hensel, M. J.; Byrn, S. R.; McKenzie, A. T.; Fuchs, P. L. J. Am. Chem. Soc. 1980, 102, 5962-5964
128. Pyne, S. G.; Hensel, M. J.; Fuchs, P. L. J. Am. Chem. Soc. 1982, 104, 5719-5728
129. Yamada, H.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1991, 56, 4569-4574
130. Castro, B. R. Org. React. 1983, 29, 1-162
131. Hughes, D. L. Org. React. 1992, 42, 335-656
132. Ojima, I.; McCullagh, J. V.; Shay, W. R. J. Organomet. Chem. 1996, 521, 421-423
133. Stamos, D. P.; Taylor, A. G.; Kishi, Y. Tetrahedron Lett. 1996, 37, 8647-8650
134. Kahn, S. D.; Pau, C. F.; Chamberlin, A. R.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 650-663
135. Lambert, J. B.; Wang, G.-T.; Finzel, R. B.; Teramura, D. H. J. Am. Chem. Soc. 1987, 109, 7838-7845
136. Lambert, J. B.; Chelius, E. C. J. Am. Chem. Soc. 1990, 112, 8120-8126
137. Lambert, J. B. Tetrahedron 1990, 46, 2677-2689
138. Lambert, J. B.; Liu, X. J. Organomet. Chem. 1996, 521, 203-210
139. Lambert, J. B.; Zhao, Y.; Emblidge, R. W.; Salvador, L. A.; Liu, X.; So, J. H.; Chelius, E. C. Acc. Chem. Res. 1999, 32, 183-190
140. For a review on the β-effect, see: White, J. M.; Clark, C. I. Top. Stereochem. 1999, 22, 137-200
141. Denmark, S. E.; Sweis, R. F.; Wehrli, D. J. Am. Chem. Soc. 2004, 126, 4865-4875
142. Denmark, S. E.; Pan, W. Org. Lett. 2001, 3, 61-64
143. Denmark, S. E.; Pan, W. Org. Lett. 2001, 3, 4163-4166
144. Denmark, S. E.; Pan, W. Org. Lett. 2001, 3, 1119-1122
145. Denmark, S. E.; Yang, S.-M. Org. Lett. 2001, 3, 1749-1752
146. Denmark, S. E.; Yang, S.-M. Tetrahedron 2004, 60, 9695-9708
147. Halpern, M.; Sasson, Y.; Rabinovitz, M. Tetrahedron 1982, 38, 3183-3187
148. Pliego, J. R., Jr.; Piló-Veloso, D. Phys. Chem. Chem. Phys. 2008, 10, 1118-1124
149. Denmark, S. E.; Sweis, R. F. Org. Lett. 2002, 4, 3771-3774
150. Denmark, S. E.; Muhuhi, J. M. J. Am. Chem. Soc. 2010, 132, 11768-11778