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
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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
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Año: | 1986
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Volumen: | 69
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Número: | 8
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Página de inicio: | 1844
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Página de fin: | 1850
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DOI: |
http://dx.doi.org/10.1002/hlca.19860690810 |
Título revista: | Helvetica Chimica Acta
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Título revista abreviado: | Helv. Chim. Acta
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ISSN: | 0018019X
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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
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- Chang, F.C., (1979) J. Org. Chem., 44, p. 4567
- Chang, F.C., (1958) J. Am. Chem. Soc., 80, p. 2906
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- 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
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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