Navegar

Colección

Datos Estadísticas

Artículo

Estamos trabajando para incorporar este artículo al repositorio
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

Enantiomerically pure (4R)-4-hydroxymethyl-4-thiobutyro-1,4-lactone [(5R)-dihydro-5-(hydroxymethyl)-2(3H)-thiophenone (12)] and derivatives were synthesized by two enantiospecific sequences employing D-ribono-1,4-lactone (1) and L-glutamic acid (6) as chiral templates. The key step in the first approach was the SmI2-promoted 2,3-deoxygenation of a 4-thio-L-lyxono-1,4-lactone derivative, prepared from 1. The other strategy, which starts from 6, involves the (5S)-dihydro-5-(p-tolylsulfonyloxymethyl)-2-(3H)-furanone (8) as chiral precursor. This was converted into a 4,5-thiirane derivative via the corresponding 4,5-epoxide. Regioselective opening of the thiirane ring by acetate followed by O-deacetylation gave 12 (40% overall yield from 8). Copyright (C) 2000 Elsevier Science Ltd.

Registro:

Documento: Artículo
Título:Two approaches to the enantioselective synthesis of (4R)-(-)-4-hydroxymethyl-4-thiobutyro-1,4-lactone
Autor:Zunszain, P.A.; Varela, O.
Filiación:CIHIDECAR-CONICET, Depto. Quim. Organ., Fac. Cie. E., Buenos Aires, Argentina
Palabras clave:lactone derivative; thiolactone; article; drug synthesis; enantiomer; priority journal; stereospecificity
Año:2000
Volumen:11
Número:3
Página de inicio:765
Página de fin:771
DOI: http://dx.doi.org/10.1016/S0957-4166(99)00568-6
Título revista:Tetrahedron Asymmetry
Título revista abreviado:Tetrahedron Asymmetry
ISSN:09574166
CODEN:TASYE
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09574166_v11_n3_p765_Zunszain

Referencias:

  • Oishi, H., Noto, T., Sasaki, H., Suzuki, K., Hayashi, T., Okazaki, H., Ando, K., Sawada, M., (1982) J. Antibiotics, 35, p. 391. , (a)
  • Sasaki, H., Oishi, H., Hayashi, T., Matsuura, I., Ando, K., Sawada, M., (1982) J. Antibiotics, 35, p. 396. , (b)
  • Noto, T., Miyakawa, S., Oishi, H., Endo, H., Okazaki, H., (1982) J. Antibiotics, 35, p. 401. , (c)
  • Miyakawa, S., Suzuki, K., Noto, T., Harada, H., Okazaki, H., (1982) J. Antibiotics, 35, p. 411. , (d)
  • Omura, S., Iwai, Y., Nakagawa, A., Iwata, R., Takahashi, Y., Shimizu, H., Tanaka, H., (1983) J. Antibiotics, 36, p. 109. , (a) 11
  • Omura, S., Nakagawa, A., Iwata, R., Hatano, A., (1983) J. Antibiotics, 36, p. 1781. , (b)
  • Dolak, L.A., Castle, T.M., Truesdell, S.E., Sebek, O.K., (1986) J. Antibiotics, 39, p. 26
  • Panetta, J.A., Rapoport, H., (1982) J. Org. Chem., 47, p. 2626. , (a)
  • Li, A.-H., Moro, S., Forsyth, N., Melman, N., Ji, X.-D., Jacobson, K.A., (1999) J. Med. Chem., 42, p. 706. , (b)
  • Cruz-Almanza, R., Hernández-Quiroz, T., Breña-Valle, L.J., Pérez Flores, F., (1997) Tetrahedron Lett., 38, p. 183
  • Stevens, C.M., Tarbell, D.S., (1954) J. Org. Chem., 19, p. 1996
  • Sarpeshkar, A.M., Gossick, G.J., Wemple, J., (1979) Tetrahedron Lett., p. 703
  • Crich, D., (1988) Tetrahedron Lett., 29, p. 5805
  • Bhar, D., Chandrasekaran, S., (1997) Tetrahedron, 53, p. 11835
  • Bonini, B.F., Comes-Franchini, M., Fochi, M., Mazzanti, G., Ricci, A., (1999) Synlett, p. 486
  • Garbiras, B.J., Marburg, S., (1999) Synthesis, p. 270
  • Chambers, M.S., Thomas, E.J., (1989) J. Chem. Soc., Chem. Commun., p. 23
  • Yang, Z.Y., Xia, P., Cosentino, L.M., Lee, K.H., (1998) Bioorg. Med. Chem. Lett., 8, p. 1483
  • Stachel, H.-D., Schachtner, J., (1993) Tetrahedron, 49, p. 4871
  • Wang, C.-L., Salvino, J.M., (1984) Tetrahedron Lett., 25, p. 5243
  • Schachtner, J.E., Stachel, H.-D., Chatterjee, S.S., Hauer, H., Polborn, K., (1998) Eur. J. Med. Chem., 33, p. 665
  • Varela, O., Zunszain, P.A., (1993) J. Org. Chem., 58, p. 7860
  • Varela, O., Cicero, D., Lederkremer, R.M., (1989) J. Org. Chem., 54, p. 1884
  • Cicero, D., Varela, O., Lederkremer, R.M., (1990) Tetrahedron, 46, p. 1131
  • Cicero, D., Varela, O., Lederkremer, R.M., (1991) Carbohydr. Res., 211, p. 295
  • Cicero, D., Varela, O., (1990) Tetrahedron, 46, p. 8019
  • Zunszain, P.A., Varela, O., (1991) Carbohydr. Res., 222, p. 131
  • Inanaga, J., Katsuki, J., Yamaguchi, M., (1991) Chem. Lett., p. 1025
  • Hanessian, S., Girard, C., Chiara, J.L., (1992) Tetrahedron Lett., 33, p. 573
  • Zunszain, P.A., Varela, O., (1998) An. Asoc. Quím. Argent., 86, p. 151
  • Fujita, Y., Fukuzumi, S., Otera, J., (1997) Tetrahedron Lett., 38, p. 2121
  • Molander, G.A., Harris, C.R., (1998) Tetrahedron, 54, p. 334. , For a review on reactions of SmI2, see
  • Inanaga, J., Sakai, S., Handa, Y., Yamaguchi, M., Yokoyama, Y., (1991) Chem. Lett., p. 2117
  • Cabrera, A., Alper, H., (1992) Tetrahedron Lett., 33, p. 5007
  • Fukuzawa, S., Nakanishi, A., Fujinami, T., Sakai, S., (1988) J. Chem. Soc., Perkin Trans., 1, p. 1669
  • Ravid, U., Silverstein, R.M., Smith, L.R., (1978) Tetrahedron, 34, p. 1449
  • Kabalka, G.W., Varma, M., Varma, R.S., Srivastava, P.C., Knapp F.F., Jr., (1986) J. Org. Chem., 51, p. 2386
  • Ho, P.-T., Davies, N., (1983) Synthesis, p. 462

Citas:

---------- APA ----------
Zunszain, P.A. & Varela, O. (2000) . Two approaches to the enantioselective synthesis of (4R)-(-)-4-hydroxymethyl-4-thiobutyro-1,4-lactone. Tetrahedron Asymmetry, 11(3), 765-771.
http://dx.doi.org/10.1016/S0957-4166(99)00568-6
---------- CHICAGO ----------
Zunszain, P.A., Varela, O. "Two approaches to the enantioselective synthesis of (4R)-(-)-4-hydroxymethyl-4-thiobutyro-1,4-lactone" . Tetrahedron Asymmetry 11, no. 3 (2000) : 765-771.
http://dx.doi.org/10.1016/S0957-4166(99)00568-6
---------- MLA ----------
Zunszain, P.A., Varela, O. "Two approaches to the enantioselective synthesis of (4R)-(-)-4-hydroxymethyl-4-thiobutyro-1,4-lactone" . Tetrahedron Asymmetry, vol. 11, no. 3, 2000, pp. 765-771.
http://dx.doi.org/10.1016/S0957-4166(99)00568-6
---------- VANCOUVER ----------
Zunszain, P.A., Varela, O. Two approaches to the enantioselective synthesis of (4R)-(-)-4-hydroxymethyl-4-thiobutyro-1,4-lactone. Tetrahedron Asymmetry. 2000;11(3):765-771.
http://dx.doi.org/10.1016/S0957-4166(99)00568-6