Synthesis of Enantiopure 4-Hydroxypipecolate and 4-Hydroxylysine Derivatives from a Common 4,6-Dioxopiperidinecarboxylate Precursor

Journal of Organic Chemistry

Volumn 69, Issue 1, 2004, Pages 130-141

  Marin, J ^a,b   Didierjean, C ^c   Aubry, A ^c   Casimir, J R ^a,d   Briand, J P ^a   Guichard, G ^a  

^a INSTITUT DE BIOLOGIE MOLÉCULAIRE ET CELLULAIRE   (France)

^b Neosystem   (France)

^c UNIVERSITÉ DE LORRAINE   (France)

^d INSTITUT PASTEUR   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; REDUCTION; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

PRECURSORS; TETRAMIC ACIDS;

DERIVATIVES;

4 HYDROXY 6 OXO 1,2 PIPERIDINEDICARBOXYLATE; CARBOXYLIC ACID DERIVATIVE; HYDROXYLYSINE; PIPECOLIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REDUCTION; STEREOCHEMISTRY;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HYDROXYLYSINE; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; OXIDATION-REDUCTION; PIPECOLIC ACIDS; STEREOISOMERISM;

EID: 0346731103     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0353886     Document Type: Article

References (100)

1. Selected examples. (a) Adalinine: Lognay, G.; Hemptinne, J. L.; Chan, F. Y.; Gaspar, C. H.; Marlier, M.; Braekman, J. C.; Daloze, D.; Pasteels, J. M. J. Nat. Prod. 1996, 59, 510-511.
2. (b) Tasipeptins: Williams, P. G.; Yoshida, W. Y.; Moore, R. E.; Paul, V. J. J. Nat. Prod. 2003, 66, 620-624.
3. (c) Micropeptins: Reshef, V.; Carmeli, S. Tetrahedron 2001, 57, 2885-2894.
4. (d) Nostopeptins: Okino, T.; Qi, S.; Matsuda, H.; Murakami, M.; Yamaguchi, K. J. Nat. Prod. 1997, 60, 158-161.
5. (e) Nostocyclin: Kaya, K.; Sano, T.; Beattie, K. A.; Geoffrey, A. Tetrahedron Lett. 1996, 37, 6725-6728.
6. (f) Paraherquamides, brevianamides, and asperparalines: Williams, R. M.; Cox, R. J. Acc. Chem. Res. 2003, 36, 127-139.
7. (a) De Lucca, G. V. Bioorg. Med. Chem. Lett. 1997, 7, 501-504.
8. (b) Nishimura, Y.; Adachi, H.; Satoh, T.; Shitara, E.; Nakamura, H.; Kojima, F.; Takeuchi, T. J. Org. Chem. 2000, 65, 4871-4882.
9. (c) Minami, N. K.; Reiner, J. E.; Semple, J. E. Bioorg. Med. Chem. Lett. 1999, 9, 2625-2628.
10. (d) MacKenzie, A. R.; Marchington, A. P.; Middleton, D. S.; Newman, S. D.; Jones, B. C. J. Med. Chem. 2002, 45, 5365-5377.
11. (e) Chung, J. Y. L.; Hughes, D. L.; Zhao, D.; Song, Z.; Mathre, D. J.; Ho, G.-J.; McNamara, J. M.; Douglas, A. W.; Reamer, R. A.; Tsay, F.-R.; Varsolona, R.; McCauley, J.; Grabowski, E. J. J.; Reider, P. J. J. Org. Chem. 1996, 61, 215-222.
12. (a) Weber, K.; Ohnmacht, U.; Gmeiner, P. J. Org. Chem. 2000, 65, 7406-7416.
13. (b) Koulocheri, S. D.; Magiatis, P.; Haroutounian, S. A. J. Org. Chem. 2001, 66, 7915-7918.
14. (c) Al-Obeidi, F. A.; Micheli, B. J. M.; Barfield, M.; Padias, A. B.; Wei, Y.; Hall, H. K., Jr. Macromolecules 1999, 32, 6507-6516.
15. (d) Piró, J.; Rubiralta, M.; Giralt, E.; Diez, A. Tetrahedron Lett. 1999, 40, 4865-4868.
16. (e) De Laszlo, D. E.; Bush, B. L.; Doyle, J. J.; Greenlee, W. J.; Hangauer, D. G.; Halgren, T. A.; Lynch, R. J.; Schorn, T. W.; Siegl, P. K. S. J. Med. Chem. 1992, 35, 833-846.
17. (f) Kemp, S.; McNamara, P. E. J. Org. Chem. 1985, 50, 5834-5838.
18. For reviews on bicyclic lactams as conformationally constrained dipeptide units, see: (a) Halab, L.; Gosselin, F.; Lubell, W. D. Biopolymers 2000, 55, 101-122.
19. (b) Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789-12854.
20. Suh, Y.-G.; Kim, S.-A.; Jung, J.-K.; Shin, D.-Y.; Min, K.-H.; Koo, B.-A. ; Kim, H.-S. Angew. Chem., Int. Ed. 1999, 38, 3545-3547.
21. For a recent review, see: (a) Bailey, P. D.; Millwood, P. A.; Smith, P. D. J. Chem. Soc., Chem. Commun. 1998, 633-640.
22. For representative examples, see: (b) Micouin, L.; Varea, T.; Riche, C.; Chiaroni, A.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1994, 35, 2529-2532.
23. (c) Luker, T.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3592-3596.
24. (d) Toyooka, N.; Yoshida, Y.; Yotsui, Y.; Momose, T. J. Org. Chem. 1999, 64, 4914-4919.
25. (e) Davis, F. A.; Chao, B.; Fang, T.; Szewczyk, J. M. Org. Lett. 2000, 2, 1041-1043.
26. (f) Agami, C.; Dechoux, L.; Ménard, C.; Hebbe, S. J. Org. Chem. 2002, 67, 7573-7576.
27. (g) Hanessian, S.; van Otterlo, W. A. L.; Nilsson, I.; Bauer, U. Tetrahedron Lett. 2002, 43, 1995-1998.
28. (h) Vink, M. K. S.; Schortinghuis, C. A.; Luten, J.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. J. T. J. Org. Chem. 2002, 67, 7869-7871.
29. For representative examples, see: (a) Davis, F. A.; Fang, T.; Chao, B.; Burns, D. M. Synthesis 2000, 14, 2106-2112.
30. (b) Battistini, L.; Zanardi, F.; Rassu, G.; Spanu, P.; Pelosi, G.; Gasparri Fava, G.; Belicchi Ferrari, M.; Casiraghi, G. Tetrahedron: Asymmetry 1997, 8, 2975-2987.
31. (c) Koulocheri, S. D.; Magiatis, P.; Skaltsounis, A.-L.; Haroutounian, S. A. Tetrahedron 2002, 58, 6665-6671.
32. (d) Hanessian, S.; Reinhold, U.; Gentile, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 1881-1884.
33. For a recent review, see: Nemr, A. E. Tetrahedron 2000, 56, 8579-8629.
34. Rubiralta, M.; Diez, A.; Vila, C.; Troin, Y.; Feliz, M. J. Org. Chem. 1991, 56, 6292-6298.
35. For selected examples, see: (a) Casamitjana, N.; Amat, M.; Llor, N.; Carreras, M.; Pujol, X.; Fernández, M. M.; López, V.; Molins, E.; Miravitlles, C.; Bosch, J. Tetrahedron: Asymmetry 2003, 14, 2033-2039.
36. (b) Dias, L. C.; Fernandes, A. M. A. P.; Zukerman-Schpector, J. Synlett 2002, 1, 100-104.
37. (c) Allin, S. M.; Vaidya, D. G.; James, S. L.; Allard, J. E.; Smith, T. A. D.; McKee, V.; Martin, W. P. Tetrahedron Lett. 2002, 43, 3661-3663.
38. (d) Roussi, F.; Quirion, J.-C.; Tomas, A.; Husson, H.-P. Tetrahedron 1998, 54, 10363-10378.
39. (e) Torisawa, Y.; Nakagawa, M.; Hosaka, T.; Tanabe, K.; Lai, Z.; Ogata, K.; Nakata, T.; Oishi, T.; Hino, T. J. Org. Chem. 1992, 57, 5741-5747.
40. Kende, A. S.; Dong, H.-Q.; Mazur, A. W.; Ebetino, F. H. Tetrahedron Lett. 2001, 42, 6015-6018.
41. (b) Casimir, J. R.; Didierjean, C.; Aubry, A.; Rodriguez, M.; Briand, J.-P.; Guichard, G. Org. Lett. 2000, 2, 895-897.
42. (c) Muller, M.; Schoenfelder, A.; Didier, B.; Mann, A.; Wermuth, C.-G. Chem. Commun. 1999, 683-684.
43. (d) Karla, R.; Ebert, B.; Thorkildsen, C.; Herdeis, C.; Johansen, T. N.; Nielsen, B.; Krogsgaard-Larsen, P. J. Med. Chem. 1999, 42, 2053-2059.
44. (e) Rodriguez, M.; Aumelas, A.; Martinez, J. Tetrahedron Lett. 1990, 31, 5153-5156.
45. For a recent review, see: Weintraub, P. M.; Sabol, J. S.; Kane, J. M.; Borcherding, D. R. Tetrahedron 2003, 59, 2953-2989.
46. Meyers, A. I.; Brengel, G. P. J. Chem. Soc., Chem. Commun. 1997, 1-7.
47. (b) Micouin, L.; Jullian, V.; Quirion, J.-C.; Husson, H.-P. Tetrahedron: Asymmetry 1996, 7, 2839-2846.
48. (c) Enders, D.; Bartzen, D. Liebigs Ann./Recl. 1997, 1115-1123.
49. (d) Enders, D.; Gröbner, R.; Raabe, G.; Runsink, J. Synthesis 1996, 941-948.
50. Marin, J.; Didierjean, C.; Aubry, A.; Briand, J.-P.; Guichard, G. J. Org. Chem. 2002, 67, 8440-8449.
51. For reviews on the allylic A(1,3) strain, see: (a) Hoffmann, R. H. Angew. Chem., Int. Ed. Engl. 1992, 31, 1124-1134.
52. (b) Hoffmann, R. H. Chem. Rev. 1989, 89, 1841-1860.
53. Flynn, D. L.; Zelle, R. E.; Grieco, P. A. J. Org. Chem. 1983, 48, 2424-2426.
54. For representative examples, see: (a) Jouin, P.; Castro, B. J. Chem. Soc., Perkin Trans. 1 1987, 1177-1182.
55. (b) Fehrentz, J.-A.; Bourdel, E.; Califano, J.-C.; Chaloin, O.; Devin, C.; Garrouste, P.; Lima-Leite, A.-C.; Llinares, M.; Rieunier, F.; Vizavonna, J. ; Winternitz, F.; Loffet, A.; Martinez, J. Tetrahedron Lett. 1994, 35, 1557-1560.
56. (c) Galeotti, N.; Poncet, J.; Chiche, L.; Jouin, P. J. Org. Chem. 1993, 58, 5370-5376.
57. (d) Decicco, C. P.; Grover, P. J. Org. Chem. 1996, 61, 3534-3541.
58. (d) Ma, D.; Ma, J.; Ding, W.; Dai, L. Tetrahedron: Asymmetry 1996, 7, 2365-2370.
59. Murray, P. J.; Starkey, I. D. Tetrahedron Lett. 1996, 37, 1875-1878.
60. (a) Mannaioni, G.; Alesiani, M.; Carlà, V.; Natalini, B.; Marinozzi, M.; Pellicciari, R.; Moroni, F. Eur. J. Pharmacol. 1994, 251, 201-207.
61. (b) Lamarre, D.; Croteau, G.; Wardrop, E.; Bourgon, L.; Thibeault, D.; Clouette, C.; Vaillancourt, M.; Cohen, E.; Pargellis, C.; Yoakim, C.; Anderson, P. C. Antimicrob. Agents Chemother. 1997, 41, 965-971.
62. (c) Letavic, M. A.; Axt, M. Z.; Barberia, J. T.; Carty, T. J.; Danley, D. E.; Geoghegan, K. F.; Halim, N. S.; Hoth, L. R.; Kamath, A. V.; Laird, E. R.; Lopresti-Morrow, L. L.; McClure, K. F.; Mitchell, P. G.; Natarajan, V.; Noe, M. C.; Pandit, J.; Reeves, L.; Schulte, G. K.; Snow, S. L.; Sweeney, F. J.; Tan, D. H.; Yu, C. H. Bioorg. Med. Chem. Lett. 2002, 12, 1387-1390
63. For previous syntheses of cis-4-hydroxypipecolates, see: (a) Reference 7a.
64. (b) Lloyd, R. C.; Smith, M. E. B.; Brick, D.; Taylor, S. J. C.; Chaplin, D. A.; McCague, R. Org. Process Res. Dev. 2002, 6, 762-766.
65. (c) Celestini, P.; Danieli, B.; Lesma, G.; Sacchetti, A.; Silvani, A.; Passarella, D.; Virdis, A. Org. Lett. 2002, 4, 1367-1370.
66. (d) Kulesza, A.; Mieczkowski, A.; Jurczak, J. Tetrahedron: Asymmetry 2002, 13, 2061-2069.
67. (e) Rutjes, F. P. J. T.; Veerman, J. J. N.; Meester, W. J. N.; Hiemstra, H.; Schoemaker, H. E. Eur. J. Org. Chem. 1999, 1127-1135.
68. (f) Brooks, C. A.; Comins, D. L. Tetrahedron Lett. 2000, 41, 3551-3553.
69. (g) Di Nardo, C.; Varela, O. J. Org. Chem. 1999, 64, 6119-6125.
70. (h) Haddad, H.; Larchevêque, M. Tetrahedron: Asymmetry 1999, 10, 4231-4237.
71. (i) Bousquet, Y.; Anderson, P. C.; Bogri, T.; Duceppe, J.S.; Grenier, L. ; Guse, I. Tetrahedron 1997, 53, 15671-15680.
72. (j) Gillard, J.; Abraham, A.; Anderson, P. C.; Beaulieu, P. L.; Bogri, T.; Bousquet, Y.; Grenier, L.; Guse, I.; Lavallee, P. J. Org. Chem. 1996, 61, 2226-2231.
73. (k) Nin, A. P.; Varela, O.; de Lederkremer, R. M. Tetrahedron 1993, 49, 9459-9464.
74. For an earlier synthesis of compound 4b, see ref 18.
75. Didierjean, C.; Marin, J.; Wenger, E.; Briand, J. P.; Aubry, A.; Guichard, G. Acta Crystallogr. 2003, in press.
76. Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N.-L. Angew. Chem. Int. Ed. Engl. 1995, 34, 1555-1573.
77. 4 in the absence of AcOH.
78. In contrast, the hydroxyl and isobutyl groups in the crystal structure of 2c assume an equatorial orientation (ref 22).
79. Hutchins, R. O.; Su, W. Y.; Sivakumar, R.; Cistone, F.; Stercho, Y. P. J. Org. Chem. 1983, 48, 3412-3422.
80. For another route to δ-lactam 9 from 5a in 74% yield. see ref 14.
81. 3 has been described as an excellent reagent for the reduction of β-hydroxy ketones. Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560-3578.
82. 3 resulted in a clean deprotection of the Boc group to give 4,6-dioxopiperidine 8c in 84% yield. Didierjean, C.; Marin, J.; Wenger, E.; Briand, J. P.; Aubry, A.; Guichard, G. Acta Crystallogr. 2003, in press.
83. For recent examples, see: (a) Oba, M.; Miyakawa, A.; Nishiyama, K. J. Org. Chem. 1999, 64, 9275-9278.
84. (b) Oba, M.; Terauchi, T.; Miyakawa, A.; Nishiyama, K. Tetrahedron: Asymmetry 1999, 10, 937-945.
85. (c) Escribano, A.; Carreño, C.; Garcìa Ruano, J. L. Tetrahedron Lett. 1994, 35, 2053-2056.
86. 2, see: (a) Courcambeck, J.; Bihel, F.; De Michelis, C.; Quévéler, G.; Kraus, J.-L. J. Chem. Soc., Perkin Trans. 1 2001, 1421-1430.
87. (b) Moody, C. M.; Young, D. W. J. Chem. Soc., Perkin Trans. 1 1997, 3519-3530.
88. (c) Herdeis, C.; Hubmann, H. P. Tetrahedron: Asymmetry 1994, 5, 351-354.
89. (d) Moody, C. M.; Young, D. W. Tetrahedron Lett. 1994, 35, 7277-7280.
90. (e) Moody, C. M.; Starkmann, B. A.; Young, D. W. Tetrahedron Lett. 1994, 35, 5485-5488.
91. (f) Heffner, R. J.; Joullié, M. M. Tetrahedron Lett. 1989, 30, 7021-7024.
92. Mitsunobu, O. Synthesis 1981, 1-28.
93. Enantiopure N-acylated 2-substituted 4,5-unsaturated 6-oxopiperidines are useful building blocks, which can be further transformed in a stereocontrolled manner to give the corresponding 4-substituted derivatives. For the conjugate addition of organocuprate reagents, see refs 6h and 11c. For the conjugate addition of nitroalkanes, see: (a) Hanessian, S.; Seid, M.; Nilsson, I. Tetrahedron Lett. 2002, 43, 1991-1994.
94. Bellier, B.; Da Nascimento, S.; Meudal, H.; Gincel, E.; Roques, B. P.; Garbay, C. Bioorg. Med. Chem. Lett. 1998, 8, 1419-1424.
95. The inversion reaction in the presence of formic acid (ref 34) gave a lower yield of the corresponding trans-hydroxypipecolate.
96. (a) Meldal, M.; Juliano, M. A.; Jansson, A. M. Tetrahedron Lett. 1997, 38, 2531-2534.
97. (b) Lundquist, J. T.; Pelletier, J. C. Org. Lett. 2001, 3, 781-783.
98. Mathias, L. J. Synthesis 1979, 561-576.
99. (b) Bergmeier, S. C.; Cobas, A. A.; Rapoport, H. J. Org. Chem. 1993, 58, 2369-2376.
100. Podlech, J.; Seebach, D. Liebigs Ann. 1995, 1217-1228.