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Abstract:

3β‐Hydroxy[21‐14C]5β‐pregn‐8(14)‐en‐20‐one (17) was prepared from chenodeoxycholic acid (1a). The synthetic sequence involved: (i) degradation of the bile‐acid side chain to an etianic acid; (ii) formation of the 8(14)‐double bond; (iii) inversion of the configuration at C(3); (iv) construction of the acetyl side chain at C(17) with the required isotopic label at C(21). Structures of all described products were confirmed by chemical and spectroscopic (IR, 1H‐NMR, 13C‐NMR, MS) methods. Copyright © 1986 Verlag GmbH & Co. KGaA, Weinheim

Registro:

Documento: Artículo
Título:Synthesis of 3β‐Hydroxy[21‐14C]‐5β‐pregn‐8(14)‐en‐20‐one from Chenodeoxycholic Acid
Autor:Deluca, M.E.; Seldes, A.M.; Gros, E.G.
Filiación:Departmento de Química Orgánica Y Umymfor, Facultad de Ciencias Exactas Y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, Buenos Aires, 1428, Argentina
Año:1986
Volumen:69
Número:8
Página de inicio:1844
Página de fin:1850
DOI: http://dx.doi.org/10.1002/hlca.19860690810
Título revista:Helvetica Chimica Acta
Título revista abreviado:Helv. Chim. Acta
ISSN:0018019X
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0018019X_v69_n8_p1844_Deluca

Referencias:

  • Tschesche, R., Kleff, U., (1973) Phytochemistry, 12, p. 2375. , and refs. cited therein
  • Tschesche, R., Führer, W., Zur Biosynthese von Steroidderivaten im Pflanzenreich, XXIV. Synthese von 3β-Hydroxy-5β-pregn-8(14)-en-20-on und 3β-Acetoxy-8,14-epoxy-5β-pregnan-20-on zur Aufklärung der 14β-Hydroxylierung bei der Cardenolid-Biosynthese (1979) Chemische Berichte, 112, p. 2692
  • Beloeil, J.C., Esnault, C., Fétizon, M., Henry, R., (1979) Steroids, 35, p. 281
  • Cocker, J.D., Henbest, H.B., Phillips, G.H., Slater, G.P., Thomas, D.A., (1965), p. 6. , J. Chem. Soc; Nakanishi, S., (1964) J. Med. Chem., 7, p. 106
  • Edward, J.T., Feland, J.M., STEREOCHEMICAL STUDIES: VII. HYDROGENATION OF SOME STEROIDAL KETONES OVER ADAMS' CATALYST (1966) Canadian Journal of Chemistry, 44, p. 1311
  • Danielsson, H., Eneroth, P., Hellström, K., Sjövall, J., (1962) J. Biol. Chem., 237, p. 3657
  • Bose, A.K., Lal, B., Hoffman, W.A., III, Manhas, M.S., (1973) Tetrahedron Lett., 18, p. 1619
  • Chang, F.C., (1979) J. Org. Chem., 44, p. 4567
  • Chang, F.C., (1958) J. Am. Chem. Soc., 80, p. 2906
  • Chang, F.C., Wood, N.F., Holton, W.G., (1965) J. Org. Chem., 30, p. 1718
  • Cahiez, G., (1981) Tetrahedron Lett., 22, p. 1239
  • Mac Phillamy, H.B., Scholz, C.R., (1949) J. Biol. Chem., 178, p. 37
  • Deluca, M.E., Seldes, A.M., Garraffo, H.M., Gros, E.G., (1985) Z. Naturforsch., B, 39, p. 1617
  • Beierbeck, H., Saunders, J.K., Apsimon, J.W., The semiempirical derivation of13C nuclear magnetic resonance chemical shifts. Hydrocarbons, alcohols, amines, ketones, and olefins (1977) Canadian Journal of Chemistry, 55, p. 2813
  • Beierbeck, H., Saunders, J.K., (1976) Can. J. Chem., 54, p. 2985
  • Kametani, T., Suzuki, K., Nemoto, H., (1982) J. Org. Chem., 47, p. 2331
  • Sigg, H.P., Reichstein, T., (1956) Helvetica Chimica Acta, 39, p. 1507

Citas:

---------- APA ----------
Deluca, M.E., Seldes, A.M. & Gros, E.G. (1986) . Synthesis of 3β‐Hydroxy[21‐14C]‐5β‐pregn‐8(14)‐en‐20‐one from Chenodeoxycholic Acid. Helvetica Chimica Acta, 69(8), 1844-1850.
http://dx.doi.org/10.1002/hlca.19860690810
---------- CHICAGO ----------
Deluca, M.E., Seldes, A.M., Gros, E.G. "Synthesis of 3β‐Hydroxy[21‐14C]‐5β‐pregn‐8(14)‐en‐20‐one from Chenodeoxycholic Acid" . Helvetica Chimica Acta 69, no. 8 (1986) : 1844-1850.
http://dx.doi.org/10.1002/hlca.19860690810
---------- MLA ----------
Deluca, M.E., Seldes, A.M., Gros, E.G. "Synthesis of 3β‐Hydroxy[21‐14C]‐5β‐pregn‐8(14)‐en‐20‐one from Chenodeoxycholic Acid" . Helvetica Chimica Acta, vol. 69, no. 8, 1986, pp. 1844-1850.
http://dx.doi.org/10.1002/hlca.19860690810
---------- VANCOUVER ----------
Deluca, M.E., Seldes, A.M., Gros, E.G. Synthesis of 3β‐Hydroxy[21‐14C]‐5β‐pregn‐8(14)‐en‐20‐one from Chenodeoxycholic Acid. Helv. Chim. Acta. 1986;69(8):1844-1850.
http://dx.doi.org/10.1002/hlca.19860690810