Synthesis of 3β‐Hydroxy[21‐14C]‐5β‐pregn‐8(14)‐en‐20‐one from Chenodeoxycholic Acid
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 t...
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todo:paper_0018019X_v69_n8_p1844_Deluca2023-10-03T14:15:04Z Synthesis of 3β‐Hydroxy[21‐14C]‐5β‐pregn‐8(14)‐en‐20‐one from Chenodeoxycholic Acid Deluca, M.E. Seldes, A.M. Gros, E.G. 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 Fil:Deluca, M.E. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Seldes, A.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Gros, E.G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_0018019X_v69_n8_p1844_Deluca |
| institution |
Universidad de Buenos Aires |
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I-28 |
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R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| description |
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 |
| format |
JOUR |
| author |
Deluca, M.E. Seldes, A.M. Gros, E.G. |
| spellingShingle |
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 |
| author_facet |
Deluca, M.E. Seldes, A.M. Gros, E.G. |
| author_sort |
Deluca, M.E. |
| title |
Synthesis of 3β‐Hydroxy[21‐14C]‐5β‐pregn‐8(14)‐en‐20‐one from Chenodeoxycholic Acid |
| title_short |
Synthesis of 3β‐Hydroxy[21‐14C]‐5β‐pregn‐8(14)‐en‐20‐one from Chenodeoxycholic Acid |
| title_full |
Synthesis of 3β‐Hydroxy[21‐14C]‐5β‐pregn‐8(14)‐en‐20‐one from Chenodeoxycholic Acid |
| title_fullStr |
Synthesis of 3β‐Hydroxy[21‐14C]‐5β‐pregn‐8(14)‐en‐20‐one from Chenodeoxycholic Acid |
| title_full_unstemmed |
Synthesis of 3β‐Hydroxy[21‐14C]‐5β‐pregn‐8(14)‐en‐20‐one from Chenodeoxycholic Acid |
| title_sort |
synthesis of 3β‐hydroxy[21‐14c]‐5β‐pregn‐8(14)‐en‐20‐one from chenodeoxycholic acid |
| url |
http://hdl.handle.net/20.500.12110/paper_0018019X_v69_n8_p1844_Deluca |
| work_keys_str_mv |
AT delucame synthesisof3bhydroxy2114c5bpregn814en20onefromchenodeoxycholicacid AT seldesam synthesisof3bhydroxy2114c5bpregn814en20onefromchenodeoxycholicacid AT groseg synthesisof3bhydroxy2114c5bpregn814en20onefromchenodeoxycholicacid |
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1807318590746001408 |