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Studies on the construction of the 2-isooctyl side chain in 17-azasteroids

Untersuchungen zum Aufbau der 2-Isooctyl-Seitenkette in 17-Azasteroiden

  • Organische Chemie Und Biochemie
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Summary

The transformations of (20R)- and (20S)-3β-hydroxy-16-oxo-24-nor-17-azachol-5-eno-23-nitriles towards the 17-aza analogue of cholesterol are described. Attempts of a direct addition of a four carbon atom fragment to nitriles were unsuccessful. Alternately, nitriles were transformedvia carboxylic acids, methyl esters and primary alcohols into iodides. The coupling reaction of (20S)-iodide with (i-Bu)2CuLi afforded the desired product in low yield but failed in the case of the 20R epimer.

Zusammenfassung

Die Umsetzungen von (20R)- und (20S)-3β-Hydroxy-16-oxo-24-nor-17-azachol-5-eno-23-nitril zum 17-aza-Analogon von Cholesterin werden beschrieben. Versuche einer direkten Addition eines 4-Atom-Fragments an Nitrile verliefen erfolglos. Als Ausweg wurden die Nitrile über Carbonsäuren, Methylester und primäre Alkohole zu den lodiden umgesetzt. Die Kupplungsreaktion von (20S)-lodid mit (i-Bu)2CuLi ergab das gewünschte Produkt in niedriger Ausbeute; das (20R)-Epimere reagierte nicht.

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Authors and Affiliations

  1. Institute of Chemistry, University of Warsaw, Bialystok Branch, PL-15443, Bialystok, Poland

    J. W. Morzycki & Z. Łotowski

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  1. J. W. Morzycki
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  2. Z. Łotowski
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Morzycki, J.W., Łotowski, Z. Studies on the construction of the 2-isooctyl side chain in 17-azasteroids. Monatsh Chem 126, 119–128 (1995). https://doi.org/10.1007/BF00811765

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  • DOI: https://doi.org/10.1007/BF00811765

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