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Mikrobiologische Spaltung razemischer Steroide. Synthese vond-Aldosteron

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Summary

A racemic intermediate in the total synthesis ofd, l-aldosterone, thed, l-20-oxo-pregnene derivative I, was converted by incubation with a mold hydroxylating in the 21-position into thed-20-oxo-21-hydroxy-pregnene derivative II, whereas thel-antipode of the starting material remained unchanged. This stereospecific microbiological reaction, comprising a separation of racemic modifications, represents the last remaining step in the synthesis of naturald-aldosterone.

Other microbiological conversions of racemic steroids, dehydrogenation and hydrogenation, were also shown to proceed only with thed-enantiomer, leaving thel-form of thed, l-substrate intact.

The advantages of this new microbiological method for the resolution of racemic modifications during the total synthesis of steroids are discussed.

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Authors and Affiliations

  1. Forschungslaboratorien der CIBA Aktiengesellschaft Basel, Pharmazeutische Abteilung, Switzerland

    E. Vischer, J. Schmidlin & A. Wettstein

Authors
  1. E. Vischer
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  2. J. Schmidlin
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  3. A. Wettstein
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Vischer, E., Schmidlin, J. & Wettstein, A. Mikrobiologische Spaltung razemischer Steroide. Synthese vond-Aldosteron. Experientia 12, 50–52 (1956). https://doi.org/10.1007/BF02164671

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