The synthesis of succinic acids and derivatives. A review

Organic Preparations and Procedures International

Volumn 34, Issue 4, 2002, Pages 337-366

  Arason, K M ^a   Bergmeier, S C ^a  

^a OHIO UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SUCCINIC ACIDS;

2,2 DIETHYL 4 [3 (7 FLUORO 2 QUINOLINYLMETHOXY)ANILINO] 4 OXOBUTYRIC ACID; ACETIC ACID; ACID; ANTIASTHMATIC AGENT; BILA 257 BS; CARBON; ESTER DERIVATIVE; MATRIX METALLOPROTEINASE INHIBITOR; RENIN INHIBITOR; SC 903; SUCCINIC ACID; SUCCINIC ACID DERIVATIVE;

ALKYLATION; CATALYSIS; CHEMICAL REACTION; CONJUGATE; CYCLOADDITION; DIMERIZATION; DRUG SYNTHESIS; ENANTIOMER; OXIDATION; POLYMERIZATION; REACTION ANALYSIS; REVIEW;

EID: 0036018617     PISSN: 00304948     EISSN: 19455453     Source Type: Journal    
DOI: 10.1080/00304940209458074     Document Type: Article

References (134)

1. A. S. Franklin, J. Chem. Soc., Perkin Trans. 1,2451 (1998).
2. A. S. Franklin, J. Chem. Soc., Perkin Trans. 1, 3537 (1999).
3. R. Ikan, V. Weinstein, and U. Ravid, Org. Prep. Proced. Int., 13,59 (1981).
4. P. C. Lee, W. G. Lee, S. Y. Lee, and H. N. Chang, Biotechnol. Bioeng., 72,41 (2001).
5. R. A. Wilkinson, G. Strobel, and A. Stierle, J. Nat. Prod., 62,358 (1999).
6. J. G. Zeikus, M. K. Jain, and P. Elankovan, Appi. Microbiol. Biotechnol., 51,545 (1999).
7. C. Fumagalli, in Encyclopedia of Chemical Technology, Vol. 22 (M. Howe-Grant, ed.), Wiley, New York, 1991, p. 1074.
8. E. Ranucci, Y. Liu, M. S. Lindblad, and A. Albertsson, Macromol. Rapid Comm., 21,680 (2000).
9. R. T. Pon, S. Yu, and Y. Sanghvi, Bioconjugate Chem., 10,1051 (1999).
10. W. Jiaang, P. Tseng, and S. Chen, Synlett, 797 (2000).
11. R. T. Pon and S. Yu, Tetrahedron Lett., 38, 3327 (1997).
12. A. von Sprecher, M. Gerspacher, A. Beck, S. Kimmei, H. Wiestner, G. P. Anderson, U. Niederhauser, N. Subramanian, and M. A. Bray, Bioorg. Med. Chem. Lett., 8,965 (1998).
13. K. Strupat, J. Kampmeier, and V. Homeffer, Int. J. Mass Spectrom., 169,43 (1997).
14. L. Ladrière, A. Laghmich, F. Malaisse-Lagae, H. Dannacher, F. Björkling, and W. Malaisse, Eur. J. Pharmacol., 344, 87 (1998).
15. A. Brandi, S. Cicchi, F. M. Cordero, R. Frignoli, A. Goti, S. Picasso, and P. Vogel, J. Org. Chem., 60,6806 (1995).
16. E. Juaristi, D. Quintana, and J. Escalante, Aldrichimica Acta, 27,3 (1994).
17. F. Sänchez-Sancho, S. Valverde, and B. Herradön, Tetrahedron: Asymmetry, 7,3209 (1996).
18. D. J. Critcher, S. Connolly, and M. Wills, J. Org. Chem., 62,6638 (1997).
19. F. J. Sardina and H. Rapoport, Chem. Rev., 96,1825 (1996).
20. S. Abele and S. Dieter, Eur. J. Org. Chem., 2000,1 (2000).
21. D. A. Evans, L. D. Wu, J. J. M. Wiener, J. S. Johnson, D. H. B. Ripin, and J. S. Tedrow, J. Org. Chem., 64,6411 (1999).
22. C. Palomo, M. Oiarbide, and S. Bindi, J. Org. Chem., 63, 2469 (1998).
23. P. L. Beaulieu, J. Gillard, M. Bailey, C. Beaulieu, J.-S. Duceppe, P. Lavallee, and D. Wemic, J. Org. Chem., 64,6622 (1999).
24. C. Xue, X. He, J. Roderick, W. F. DeGrado, R. J. Chemey, K. D. Hardman, D. J. Nelson, R. A. Copel, B. D. Jaffee, and C. P. Decicco, J. Med. Chem., 41,1745 (1998).
25. J. L. Belletire and D. F. Fry, J. Org. Chem., 52,2549 (1987).
26. J. P. Kutney, N. Abdurahman, P. L. Quesne, E. Piers, and I. Vlattas, J. Am. Chem. Soc., 88,3656 (1966).
27. J. A. Girdwood and R. E. Shute, J. Chem. Soc., Chem. Commun., 2307 (1997).
28. P. Singh and S. Rangaswami, Tetrahedron Lett., 149 (1967).
29. A. Schoenfelder, A. Mann, and S. L. Coz, Synlett, 63 (1993).
30. A. Fadel and J. Salaün, Tetrahedron Lett., 29,6257 (1988).
31. R. P. Beckett, M. J. Crimmin, M. H. Davis, and Z. Spavold, Synlett, 137 (1993).
32. A.-F. Sevin, J. Seyden-Penne, and K. Boubekeur, Tetrahedron, 48,6253 (1992).
33. C. P. Decicco, D. J. Nelson, R. L. Corbett, and J. C. Dreabit, J. Org. Chem., 60,4782 (1995).
34. R. Hirayama, M. Yamamoto, T. Tsukida, K. Matsuo, Y. Obata, F. Sakamoto, and S. Ikeda, Bioorg. Med. Chem., 5,765 (1997).
35. C. P. Reddy and S. Tanimoto, J. Chem. Soc., Perkin Trans. 1,411 (1988).
36. I. Ojima, K. Yoshida, and S.-i. Inaba, Chemistry Lett., 429 (1977).
37. M.-Y. Chen and J.-M. Fang, J. Chem. Soc., Perkin Trans. 1,1737 (1993).
38. C. Mioskowski and G. Solladie, Tetrahedron, 36,227 (1980).
39. S. Brandange, S. Josephson, and S. Vallen, Acta Chem. Scand., 27,1084 (1973).
40. S. Brandange, S. Josephson, L. Morch, and S. Vallen, Acta Chem. Scand., B35,273 (1981).
41. I. C. Jacobson and G. P. Reddy, Tetrahedron Lett., 37, 8263 (1996).
42. R. W. Stevens and T. Mukaiyama, Chemistry Lett., 1799 (1983).
43. S. Kobayashi, Y. Fujishita, and T. Mukaiyama, Chemistry Lett., 2069 (1989).
44. D. A. Evans, M. C. Kozlowski, C. S. Burgey, and D. W. C. MacMillan, J. Am. Chem. Soc., 119, 7893 (1997).
45. D. A. Evans, C. S. Burgey, M. C. Kozlowski, and S. W. Tregay, J. Am. Chem. Soc., 121,686 (1999).
46. Y. Ito, M. Sawamura, H. Hamashima, T. Emura, and T. Hayashi, Tetrahedron Lett., 30,4681 (1989).
47. T. J. Brocksom, N. Petragnani, R. Rodrigues, and H. L. Teixeira, Synthesis, 396 (1975).
48. P. Renaud and M. A. Fox, J. Org. Chem., 53,3745 (1988).
49. N. Petragnani and M. Yonashiro, Synthesis, 521 (1982).
50. J. L. Belletire, E. G. Spletzer, and A. R. Pinhas, Tetrahedron Lett., 25,5969 (1984).
51. J. L. Belletire and D. F. Fry, J. Org. Chem., 53,4724 (1988).
52. J. L. Belletire and S. L. Fremont, Tetrahedron Lett., 27,127 (1986).
53. N. Kise, K. Tokioka, Y. Aoyama, and Y. Matsumura, J. Org. Chem., 60,1100 (1995).
54. N. A. Porter, Q. Su, J. J. Harp, I. J. Rosenstein, and A. T. McPhail, Tetrahedron Lett., 34,4457 (1993).
55. T. Langer, M. Illich, and G. Helmchen, Tetrahedron Lett., 36,4409 (1995).
56. I. Ojima, S. M. Brandstadter, and R. J. Donovan, Chemistry Lett., 1591 (1992).
57. S.-i. Inaba and I. Ojima, Tetrahedron Lett., 2009 (1977).
58. M. W. Rathke and A. Lindert, J. Am. Chem. Soc., 93,4605 (1971).
59. I. Kuwajima and Y. Doi, Tetrahedron Lett., 1163 (1972).
60. R. H. Frazier Jr. and R. L. Harlow, J. Org. Chem., 45,5408 (1980).
61. W. G. Kofion and C. R. Hauser, J. Org. Chem., 35,2085 (1970).
62. S. K. Chung and L. B. Dunn Jr., J. Org. Chem., 48,1125 (1983).
63. J. H. Babler and S. J. Sarussi, J. Org. Chem., 52,3462 (1987).
64. Y. Kobayashi, T. Taguchi, T. Morikawa, E. Tokuno, and S. Sekiguchi, Chem. Pharm. Bull., 28, 262 (1980).
65. N. Kise, K. Kumada, Y. Terao, and N. Ueda, Tetrahedron, 54,2697 (1998).
66. Y. Matsumura, M. Nishimura, H. Hiu, M. Watanabe, and N. Kise, J. Org. Chem., 61,2809 (1996).
67. M. Tokuda, T. Shigei, and M. Itoh, Chemistry Lett., 621 (1975).
68. E. Balaux and R. Ruel, Tetrahedron Lett., 37, 801 (1996).
69. A. Yamada, S. Grossman, and O. Vogl, J. Polym. Sei., Polym. Chem. Ed., 18,1739 (1980).
70. R. Schlecker and D. Seebach, Helv. Chim. Acta, 60,1459 (1977).
71. Y. Endo and K. Shudo, Tetrahedron Lett., 32,4517 (1991).
72. I. V. Magedov and Y. I. Smushkevich, J. Chem. Soc., Chem. Cotnrnm., 1686 (1990).
73. Y. Endo, T. Uchida, S. Hizatate, and K. Shudo, Synthesis, 1096 (1994).
74. T. Uchida, Y. Endo, S. Hizatate, and K. Shudo, Chem. Pharm. Bull., 42,419 (1994).
75. S. J. Miller and C. D. Bayne, J. Org. Chem., 62,5680 (1997).
76. H. Wynberg and E. G. J. Staring, J. Am. Chem. Soc., 104,166 (1982).
77. J.-P. Depres, F. Coelho, and A. E. Greene, J. Org. Chem., 50,1972 (1985).
78. R. B. Davis and J. A. Ward Jr., Org. Syn. Coll. Vol., 4,392 (1963).
79. R. V. Whiteley Jr. and R. S. Marianelli, Synthesis, 392 (1978).
80. N. Dahuron and N. Langlois, Synlett, 51 (1996).
81. J. N. Freskos, S. A. Laneman, M. L. Reilly, and D. A. Ripin, Tetrahedron Lett., 35, 835 (1994).
82. K. Yamamoto, R. Deguchi, and J. Tsuji, Bull. Chem. Soc. Jpn., 58,3397 (1985).
83. J. Tsuji and T. Mandai, Angew. Chem. Int. Ed. Eng., 34,2589 (1995).
84. W. S. Johnson and G. H. Daub, Org. Reactions, 6,1 (1951).
85. A. Ramazani and A. Bodaghi, Tetrahedron Lett., 41,567 (2000).
86. A. Cabrera and H. Alper, Tetrahedron Lett., 33,5007 (1992).
87. R. Kuwano, M. Sawamura, and Y. Ito, Tetrahedron: Asymmetry, 6,2521 (1995).
88. L. Shao, S. Miyata, H. Muramatsu, H. Kawano, Y. Ishii, M. Saburi, and Y. Uchida, J. Chem. Soc., Perkin Trans. 1,1441 (1990).
89. H. Jendralla, R. Henning, B. Searing, J. Herden, B. Kulitzsher, and J. Wunner, Synlett, 155 (1993).
90. T. Morimoto, M. Chiba, and K. Achivva, Tetrahedron, 49,1793 (1993).
91. H. Kawano, Y. Ishii, T. Ikariya, M. Saburi, S. Yoshikawa, Y. Uchida, and H. Kumobayashi, Tetrahedron Lett., 28,1905 (1987).
92. U. Berens, M. Burk, A. Gerlach, and W. Hems, Angew. Chem. Int. Ed., 39,1981 (2000).
93. J. M. Harris, E. A. Bolessa, A. J. Mendonca, S. Feng, and J. C. Vederas, J. Chem. Soc., Perkin Trans. 1,1945 (1995).
94. N. R. Long and M. W. Rathke, Synth. Commun., 11,687 (1981).
95. M. P. Sibi and P. K. Deshpande, J. Chem. Soc., Perkin Trans. 1,1461 (2000).
96. G. Bashiardes, S. P. Collingwood, S. G. Davies, and S. C. Preston, J. Chem. Soc., Perkin Trans. 1,1162 (1989).
97. L. M. Pratt, S. A. Bowles, S. F. Courtney, C. Hidden, C. N. Lewis, F. M. Martin, and R. S. Todd, Synlett, 531 (1998).
98. S. Yoshida, T. Ogiku, H. Ohmizu, and T. Iwasaki, Synthesis, 1475 (1997).
99. W. G. Kofron and L. G. Wideman, J. Org. Chem., 37, 555 (1972).
100. G. Calderari and D. Seebach, Hetv. Chim. Acta, 68,1592 (1985).
101. S. C. Bergmeier and K. A. Ismail, Synthesis, 1369 (2000).
102. C. P. Decicco, Y. Song, and D. A. Evans, Org. Lett., 3,1029 (2001).
103. L. I. Krimen, Org. Synth., 50,1 (1970).
104. J. S. Bajwa and M. J. Miller, J. Org. Chem., 48,1114 (1983).
105. D. Wasmuth, D. Arigoni, and D. Seebach, Helv. Chim. Acta, 65,344 (1982).
106. D. Seebach, J. D. Aebi, and D. Wasmuth, Org. Synth., 63,109 (1985).
107. K. K. Mahalanabis, M. Mumtaz, and V. Snieckus, Tetrahedron Lett., 23,3975 (1982).
108. K. K. Mahalanabis, M. Mumtaz, and V. Snieckus, Tetrahedron Lett., 23,3971 (1982).
109. A. Misumi, K. Iwanaga, K. Furuta, and H. Yamamoto, J. Am. Chem. Soc., 107,3343 (1985).
110. S. B. Hoyt and L. E. Overman, Org. Lett., 2,3241 (2000).
111. L. E. Overman, J. F. Larrow, B. A. Steams, and J. M. Vance, Angew. Chem. Int. Ed., 39,213 (2000).
112. M. Bella, F. D’Onofrio, R. Margarita, L. Parianti, G. Piancatelli, and A. Mangoni, Tetrahedron Lett., 38,7917(1997).
113. R. Eck and H. Simon, Tetrahedron, 50,13641 (1994).
114. M. S. Gulzar, M. Akhtar, and D. Gani, J. Chem. Soc., Perkin Trans. 1,649 (1997).
115. J. E. Macor, D. H. Blank, K. Ryan, and R. J. Post, Synthesis, 443 (1997).
116. H. Hansen, S. R. Jensen, and J. Munch-Petersen, Acta Chem. Scand., 26,1190 (1972).
117. A. Bernardi, S. Cardani, G. Poli, and C. Scolastico, J. Org. Chem., 51,5041 (1986).
118. A. Bernardi, S. Cardani, T. Pilati, G. Poli, C. Scolastico, and R. Villa, J. Org. Chem, 53,1600 (1988).
119. S. Cardani, G. Poli, C. Scolastico, and R. Villa, Tetrahedron, 44,5929 (1988).
120. I. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley, London, 1980, p. 87.
121. M. C. Kloetzel, Org. Reactions, 4,1 (1948).
122. W. Oppolzer, in Comprehensive Organic Synthesis: Selectivity, Strategy and Efficiency in Modem Organic Chemistry, Vol. 5 (B. M. Trost and I. Fleming, eds.), Pergamon Press, Oxford, England, 1991, p. 315.
123. W. Carruthers, Cycloaddition Reactions in Organic Synthesis, Pergamon Press, Elmsford, New York, 1990.
124. K. L. Williamson, Macroscale and Microscale Organic Experiments, D. C. Heath and Co., Lexington, MA, 1989, p. 322.
125. T. Durst, E. C. Kozma, and J. L. Charlton, J. Org. Chem., 50,4829 (1985).
126. D. H. Kim and S. Chung, Tetrahedron: Asymmetry, 10, 376 (1999).
127. J. R. Casimir, L. Ettouati, and J. Paris, Lett. Pept. Sei., 5,13 (1998).
128. J. K. Whitesell, K. Nabona, and D. Deyo, J. Org. Chem., 54, 2258 (1989).
129. S. V. Frye and E. L. Eliel, Tetrahedron Lett., 26,3907 (1985).
130. G. J. Dawson, J. M. J. Williams, and S. J. Coote, Tetrahedron: Asymmetry, 6, 2535 (1995).
131. N. Kurose, T. Takahashi, and T. Koizumi, J. Org. Chem., 62,4562 (1997).
132. S. J. Brown, S. Corr, and J. M. Percy, Tetrahedron Lett., 41,5269 (2000).
133. I. W. Lawston and T. D. Inch, J. Chem. Soc., Perkin Trans. 1, 2629 (1983).
134. S. Yang, W. Hayden, K. Faber, and H. Gringl, Synthesis, 365 (1992).