Preparation of Phosphostatine Analogues From L-amino acids
DOI:
https://doi.org/10.29356/jmcs.v49i4.1321Keywords:
Phosphostatine, aminophosphonic acids, β-ketophosphonates, diastereoselective reductionAbstract
Abstract. Reduction of (3S)-N,N-dibenzylamino-2-ketophosphonates
9a-d derived from L-amino acids was carried out with catecholborane
at -20 °C to afford the (3S)-N,N-dibenzylamino-(2R)-hydroxy-phosphonates syn-10a-d, whereas the reduction of (3S)-N-benzylamino-2-ketophosphonates 13a-d with Zn(BH4)2 at -78 °C yield (3S)-N-benzylamino-(2S)-hydroxyphosphonates anti-14a-d. The reduction in both cases was in good chemical yields and with high diastereoselectivity. The hydrolysis and hydrogenolysis of 10a-d and 14a-d afford the (3S)-amino-(2R)-hydroxyphosphonic acids 6 and (3S)-amino-(2S)-hydroxyphosphonic acids 7, respectively, which are analogues of phosphostatine.
Resumen. La reducción de (3S)-N,N-dibencilamino-2-cetofosfonatos
9a-d preparados a partir de L-aminoácidos se llevó a cabo con catecolborano a -20 °C, obteniendo los (3S)-N,N-dibencilamino-(2R)-
hidroxifosfonatos syn-10a-d, mientras que la reducción de los (3S)-Nbencilamino-2-cetofosfonatos 13a-d con Zn(BH4)2 a -78 °C produce
los (3S)-N-bencilamino-(2S)-hidroxifosfonatos anti-14a-d. La reducción
en ambos casos procede con buen rendimiento químico y con una alta diastereoselectvidad. La hidrólisis e hidrógenolisis de los hidroxifosfonatos 10a-d y 14a-d proporciona a los ácidos (3S)-amino-(2R)-hidroxi-fosfónicos 6 y (3S)-amino-(2S)-hidroxifosfónicos 7, respectivamente, los cuales son análogos de la fosfoestatina.
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References
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11. The preparation of 2-ketophosphonates 9a-d have been described, although to the best of our knowledge no data given: see ref. 10d.
12. (a) Preliminar results have been described by us, see: Ordóñez, M.; De la Cruz-Cordero, R.; Fernández-Zertuche, M.; Muñoz- Hernández, M. A. Tetrahedron: Asymmetry 2002, 13, 559-562. (b) De la Cruz-Cordero, R.; Hernández-Núñez, E.; Fernández-Zertuche, M.; Muñoz-Hernández, M. A.; Ordóñez, M. ARKIVOC 2005 (vi), 277-286.
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18. The mixture of the diastereomers anti-14 and syn-15 was treated with benzyl bromide and K2CO3 in acetonitrile at room temperature to afford the mixture of the already known 3-N,N-dibenzylamino-
2-hydroxyphosphonates syn-10 and anti-11.
19. (a) Pikul, S.; Dunham, K. L. M.; Almstead, N. G.; De, B.; Natchus, M. G.; Anastasio, M. V.; McPhail, S. J.; Snider, C. E.; Taiwo, Y. O.; Chen, L.; Dunaway, C. M.; Gu, F.; Mieling, G. E. J. Med. Chem. 1999, 42, 87-94. (b) Paradisi, F.; Porzi, G.; Sandri, S. Tetrahedron: Asymmetry 2001, 12, 3319-3324. (c) Verardo,
G.; Geatti, P.; Pol, E.; Giumanini, A. G. Can. J. Chem. 2002, 80, 779-788.
20. Pelter, A.; Smith, K.; Brown, H. Borane Reagents, Academic Press, London, 1988, pp. 414.
2. For recent synthetic methodologies of statine and their analogues, see: (a) Yuste, F.; Diaz, A.; Ortiz, B.; Sánchez-Obregón, R.; Walls, F.; García-Ruano, J. L. Tetrahedron: Asymmetry 2003, 14, 549-554. (b) Yoo, D.; Oh, J. S.; Kim, Y. G. Org. Lett. 2002, 4, 1213-1215. (c) Kwon, S. J.; Ko, S. Y. Tetrahedron Lett. 2002, 43, 639-641. (d) Ko, S. Y. J. Org. Chem. 2002, 67, 2689-2691. (e) Pasenti, C.; Bravo, P.; Corradi, E.; Frigerio, M.; Meille, S. V.; Panzeri, W.; Viani, F.; Zanda, M. J. Org. Chem. 2001, 66, 5637-5640. (f) Travins, J. M.; Bursavich, M. G.; Veber, D. F.; Rich, D. H. Org. Lett. 2001, 3, 2725-2728. (g) Hoffman, R. V.; Tao, J. J. Org. Chem. 1997, 62, 2292-2297. (h) Sengupta, S.; Sarma, D. S. Tetrahedron: Asymmetry 1999, 10, 4633-4637. (i) Lee, K.-Y.; Kim, H.-Y.; Park, M.-S.; Oh, C.-Y.; Ham, W.-H. J. Org. Chem. 1999, 64, 9450-9458. (j) Alemay, C.; Bach, J.; Farras, J.; García, J. Org. Lett. 1999, 1, 1831-1834. (k) Reddy, G. V.; Rao, G. V.;
Iyengar, D. S. Tetrahedron Lett. 1999, 40, 775-776. (l) Aoyagi, Y.; Williams, R. M. Tetrahedron 1998, 54, 10419-10433. (m) Veeresha, G.; Datta, A. Tetrahedron Lett. 1997, 38, 5223-5224. (n) Gennari, C.; Moresca, D.; Vulpetti, A.; Pain, G. Tetrahedron 1997, 53, 5593-5608. (o) Ma, D.; Ma, J.; Ding, W.; Dai, L.
Tetrahedron: Asymmetry 1996, 7, 2365-2370.
3. Kukhar, V. P.; Hudson H. R., Eds. Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity. John Wiley: New York, 2000 and references therein.
4. (a) Nieschalk, J.; Batsanov, A. S.; O’Hagan, D.; Howard, J. A. K. Tetrahedron 1996, 52, 165. (b) Burke Jr. T. R.; Smyth, M. S.; Nomizu, M.; Otaka, A.; Roller, P. P. J. Org. Chem. 1993, 58, 1336-1340.
5. (a) Dellaria, J. F., Jr.; Maki, R. G.; Stein, H. H.; Cohen, J.; Whittern, D.; Marsh, K.; Hoffman, D. J.; Plattner, J. J.; Perum, T. J. J. Med. Chem. 1990, 33, 534-542. (b) Dellaria, J. F.; Maki, R. G. Tetrahedron Lett. 1986, 27, 2337-2340.
6. Chakravarty, P. K.; Greenlee, W. J.; Parsons, W. H.; Patchett, A. A.; Combs, P.; Roth, A.; Busch, R. D.; Melllin, T. N. J. Med. Chem. 1989, 32, 1886-1890.
7. (a) Drag, M.; Latjka, R.; Gumienna-Kontecka, E.; Kozlowski, H.; Kafarski, P. Tetrahedron: Asymmetry 2003, 14, 1837-1845. (b) Wróblewski, A. E.; Piotrowska, D. G. Tetrahedron: Asymmetry 2002, 13, 2509-2512 and references therein. (c) Hammerschmidt, F.; Wolfgang, W.; Wuggenig, F.; Zarbl, E. Tetrahedron: Asymmetry 2000, 11, 2955-2964. (d) Hammerschmidt, F.; Lindner, W.; Wuggenig, F.; Zarbl, E. Tetrahedron: Asymmetry 2000, 11, 2955-2964. (e) Barco, A.; Benetti, S.; Bergamini, P.;
De Risi, C.; Marchetti, P.; Pollini, G. P.; Zanirato, V. Tetrahedron Lett. 1999, 40, 7705-7708. (f) Thomas, A. A.; Sharpless, K. B. J. Org. Chem. 1999, 64, 8379-8385. (g) Gravotto, G.; Giovenzana, G. B.; Pagliarin, R.; Palmisano, G.; Sisti, M. Tetrahedron: Asymmetry 1998, 9, 745-748.
8. Yamagishi, T.; Fujii, K.; Shibuya, S.; Yokomatsu, T. Synlett, 2004, 2505-2508.
9. (a) Ordóñez, M.; González-Morales, A.; Ruiz, C.; De la Cruz-Cordero, R.; Fernández-Zertuche, M. Tetrahedron: Asymmetry 2003, 14, 1775-1779. (b) Ordóñez, M.; González-Morales, A.; Salazar-Fernández, H. Tetrahedron: Asymmetry 2004, 15, 2719-2725.
10. (a) Reetz, M. T.; Drewes, M. W.; Schmitz, A. Angew. Chem. Int. Ed. Engl. 1987, 26, 1141-1143. (b) Cooke, J. W. B.; Davies, S. G.; Naylon, A. Tetrahedron 1993, 49, 7955-7966. (c) Beaulieu, P. L.; Wernic, D. J. Org. Chem. 1996, 61, 3635-3645. (d) Chung, S.-K.; Kang, D.-H. Tetrahedron: Asymmetry 1997, 8, 3027-3030.
11. The preparation of 2-ketophosphonates 9a-d have been described, although to the best of our knowledge no data given: see ref. 10d.
12. (a) Preliminar results have been described by us, see: Ordóñez, M.; De la Cruz-Cordero, R.; Fernández-Zertuche, M.; Muñoz- Hernández, M. A. Tetrahedron: Asymmetry 2002, 13, 559-562. (b) De la Cruz-Cordero, R.; Hernández-Núñez, E.; Fernández-Zertuche, M.; Muñoz-Hernández, M. A.; Ordóñez, M. ARKIVOC 2005 (vi), 277-286.
13. (a) Cherest, M.; Felkin, H. Tetrahedron Lett. 1968, 18, 2199-2200. (b) Cherest, M.; Felkin, H. Tetrahedron Lett. 1968, 18, 2205-2208. (c) Anh, N. T.; Eisenstein, O. Nouv J. Chem. 1977, 1, 61. (d) For an excellent summary, see: Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; John Wiley and Sons: New York, 1994: pp 876.
14. Barluenga, J.; Baragaña, B.; Concellón, J. M. J. Org. Chem. 1995, 60, 6696-6699.
15. (a) Hoffmann, R. V.; Maslouh, N.; Cervantes-Lee, F. J. Org. Chem. 2002, 67, 1045. (b) Reetz, M. T.; Schmitz, A. Tetrahedron Lett. 1999, 40, 2741-2742.
16. Concellón, J. M.; Bernard, P. L.; Riego, E.; García-Granda, S.; Forcén-Acebal, A. J. Org. Chem. 2001, 66, 2764-2768.
17. Preliminary results have been reported by us, see: Ordóñez. M.; De la Cruz-Cordero, R.; Quiñónes, C.; González-Morales, A. J. Chem. Soc. Chem. Commun. 2004, 672-673.
18. The mixture of the diastereomers anti-14 and syn-15 was treated with benzyl bromide and K2CO3 in acetonitrile at room temperature to afford the mixture of the already known 3-N,N-dibenzylamino-
2-hydroxyphosphonates syn-10 and anti-11.
19. (a) Pikul, S.; Dunham, K. L. M.; Almstead, N. G.; De, B.; Natchus, M. G.; Anastasio, M. V.; McPhail, S. J.; Snider, C. E.; Taiwo, Y. O.; Chen, L.; Dunaway, C. M.; Gu, F.; Mieling, G. E. J. Med. Chem. 1999, 42, 87-94. (b) Paradisi, F.; Porzi, G.; Sandri, S. Tetrahedron: Asymmetry 2001, 12, 3319-3324. (c) Verardo,
G.; Geatti, P.; Pol, E.; Giumanini, A. G. Can. J. Chem. 2002, 80, 779-788.
20. Pelter, A.; Smith, K.; Brown, H. Borane Reagents, Academic Press, London, 1988, pp. 414.
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