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Updated: Mar 21, 2026

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Concise Approach to (ent)-14 β-Hydroxysteroids through Highly Diastereo-/Enantioselective Diels-Alder Reactions
Clovis Peter1, Blandine Ressault1, Philippe Geoffroy1
1Université de Strasbourg, Institut de Chimie - UMR 7177, 1 rue Blaise Pascal, BP296/R8-67008, Strasbourg Cedex, France.
Abstract:
14β-Hydroxysteroids, especially 14β-hydroxyandrostane derivatives are closely related to the cardenolide skeletons. The latter were readily available through highly diastero/enantioselective Diels-Alder (DA) reactions requiring high pressure or Lewis acid activation. Moreover, in the presence of (R)- or (S)-carvone as a chiral dienophile, the DA-reaction takes place under chemodivergent parallel kinetic resolution control affording highly enantiomerically enriched 14β-hydroxysteroid derivatives or the corresponding (ent)-14β-hydroxysteroid derivatives.
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