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The Synthesis of D-Heteroannulated 3β-Hydroxy-13α-androst-5-ene Derivatives via α-Oxoketene Dithioacetal and α-Oxohydroxymethylidene Synthons

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Summary.

16-Ketene dithioacetal derivatives of 3β-hydroxy-13α-androst-5-en-17-one react with amidine, benzamidine, or guanidine to yield novel pyrimido-fused D-heteroannulated steroids. The reactions of 3β-hydroxy-16-hydroxymethylidene-13α-androst-5-en-17-one with N,N′-dinucleophiles furnish heterocycles containing a pyrazole ring fused to positions 16,17 of the sterane skeleton.

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Authors and Affiliations

  1. Department of Organic Chemistry, University of Szeged, Szeged, Hungary

    Ágota Szájli & János Wölfling

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  1. Ágota Szájli
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  2. János Wölfling
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Correspondence to János Wölfling.

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Szájli, Á., Wölfling, J. The Synthesis of D-Heteroannulated 3β-Hydroxy-13α-androst-5-ene Derivatives via α-Oxoketene Dithioacetal and α-Oxohydroxymethylidene Synthons. Monatsh. Chem. 137, 1431–1440 (2006). https://doi.org/10.1007/s00706-006-0544-7

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  • DOI: https://doi.org/10.1007/s00706-006-0544-7

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