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Synthesis of 3β-Hydroxy[21-14C]-5β-pregn-8(14)-en-20-one from Chenodeoxycholic Acid (1986)

Deluca, MóNica E. ; Seldes, Alicia M. ; Gros, Eduardo G.

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 69 (1986), S. 1844-1850

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ISSN: 0018-019X

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: 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.

Additional Material: 1 Tab.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/hlca.19860690810

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