Efficient and Practical Synthesis of syn- and anti-b,g- Dihydroxyphosphonates Derived from (S)-Mandelic Acid
DOI:
https://doi.org/10.29356/jmcs.v51i4.1289Keywords:
Diastereoselective 1,2-induction, diastereoselective reduction, b,g-dihydroxyphosphonates, b-ketophosphonates, (S)-mandelic acidAbstract
Abstract: A new efficient and practical synthesis of syn- and antib, g-dihydroxyphosphonates 1 and 2 was developed in high diastereoselectivity via reduction of b-ketophosphonates readily obtained from (S)-mandelic acid. An example of “diastereoselective 1,2-induction” is showed and a mechanistic model to explain the stereochemical outcome is proposed. Assignment of the configuration at the new stereogenic centers was achieved by 1H NMR spectral data of their corresponding acetonides.
Resumen: Se describe una nueva síntesis eficiente y práctica de syny anti-b,g-dihidroxifosfonatos 1 y 2 mediante la reducción diastereoselectiva de b-cetofosfonatos fácilmente preparados a partir de ácido (S)-mandélico. Esta metodología representa un ejemplo de inducción “diastereoselectiva 1,2” y se propone un modelo mecanístico para explicar la alta diastereoselectividad. La configuración absoluta del nuevo centro estereogénico se llevó a cabo mediante el análisis de los espectros de RMN de 1H de sus correspondientes acetales cíclicos.
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References
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11. Huang, J.; Chen, R. Heteroatom Chem. 2000, 11, 480-492.
12. (a) Maier, L.; Diel, P. J. Phosphorous, Sulfur, Silicon 1994, 90, 259-279. (b) Maier, L.; Diel, P. J. Phosphorous, Sulfur, Silicon 1991, 57, 57-64.
13. Lavielle, G.; Hautefaye, P.; Schaeffer, C.; Boutin, J. A.; Cudennec, C. A.; Pierré, A. J. Med. Chem. 1991, 34, 1998-2003.
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15. (a) Kametani, T.; Kigasawa, K.; Hiiragi, M.; Wakisaka, K.; Kaga, S.; Sugi, H.; Tanigawa, K.; Suziki, Y.; Fukawa, K.; Irino, O.; Saita, O.; Yamabe, S. Heterocycles 1981, 16, 1205-1242. (b) Baylis, E. K.; Campbell, C. D.; Dingwall, J. G. J. Chem. Soc., Perkin Trans. 1 1984, 2845-2853. (c) Lejczak, B.; Kafarski, P.;
Sztajer, H.; Mastalerz, P. J. Med. Chem. 1986, 29, 2212-2217. (d) Okada, Y.; Iguchi, S.; Mimura, M.; Yagyu, M. Chem. Pharm. Bull. 1980, 28, 1320-1323.
16. (a) Hirschmann, R.; Smith, A. B.; Taylor, C. M.; Benkovic, P. A.; Taylor, S. D.; Yager, K. M.; Sprengler, P. A.; Benkovic, S. J. Science 1994, 265, 234-237. (b) Smith, A. B., III.; Taylor, C. M.; Bencovic, S. J.; Hirschmann, R. Tetrahedron Lett. 1994, 35, 6853-6856.
17. (a) Koh, Y.; Shim, J. H.; Wu, J. Z.; Zhong, W.; Hong, Z.; Girardet, J.-L. J. Med. Chem. 2005, 48, 2867-2875. (b) Kobayashi, Y.; William, A. D.; Tokoro, Y. J. Org. Chem. 2001, 66, 7903-7906. (c) Page, P.; Blonski, C.; Périé, J. Bioorg. Med. Chem. 1999, 7, 1403-1412.
18. (a) Nakamura, K.; Yamamura, S. Tetrahedron Lett. 1997, 38, 437- 438. (b) Li, Z.; Racha, S.; Dan, L.; El-Subbagh, H.; Abushanab, E. J. Org. Chem. 1993, 58, 5779-5783. (a) Racha, S.; Li, Z.; El-Subbagh, H.; Abushanab, E. Tetrahedron Lett. 1992, 33, 5491-5494.
19. (a) Kolodiazhna, A. O.; Kukhar, V. P.; Chernega, A. N.; Kolodiazhnyi, O. I. Tetrahedron: Asymmetry 2004, 15, 1961-1963. (b) Bongini, A.; Camerini, R.; Panunzio, M.; Bandini, E.; Martelli, G.; Spunta, G. Tetrahedron: Asymmetry 1996, 7, 3485- 3504. (c) Yokomatsu, T.; Yamagishi, T.; Shibuya, S. Tetrahedron: Asymmetry 1993, 4, 1779-1782.
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