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Issue 0, 1985
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Reduction of α-diazo-β-hydroxy esters to β-hydroxy esters: application in one of two convergent syntheses of a (22S)-22-hydroxy bile acid from fish bile and its (22R)-epimer

Roberto Pellicciari,  Benedetto Natalini,  Sergio Cecchetti  and  Renata Fringuelli 

Abstract

α-Diazo-β-hydroxy esters (3) prepared by condensation of aldehydes (1) with ethyl (lithio) diazoacetate (2) are reduced with 5% palladium over charcoal in methanol into the corresponding β-hydroxy esters (5) in high yield. This sequence is applied to a new synthesis of haemulcholic acid (14c), a (22S)-22-hydroxy bile acid from fish bile and its (22R)-epimer (14d). A convergent synthesis of (14c), a (22S)-22-hydroxy bile acid from fish bile and its (22R)-epimer (14d). A convergent synthesis of (14c) and (14d) involves, as a key step, the dirhodium (II) tetra-acetate conversion of (12) into the corresponding β-keto ester (13).

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Article type: Paper
DOI: 10.1039/P19850000493
Citation: J. Chem. Soc., Perkin Trans. 1, 1985,0, 493-497
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    Reduction of α-diazo-β-hydroxy esters to β-hydroxy esters: application in one of two convergent syntheses of a (22S)-22-hydroxy bile acid from fish bile and its (22R)-epimer

    R. Pellicciari, B. Natalini, S. Cecchetti and R. Fringuelli, J. Chem. Soc., Perkin Trans. 1, 1985, 0, 493
    DOI: 10.1039/P19850000493

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