Concise Approach to (ent)‐14 β‐Hydroxysteroids through Highly Diastereo‐/Enantioselective Diels–Alder Reactions |
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Authors: | Clovis Peter Dr Blandine Ressault Dr Philippe Geoffroy Dr Michel Miesch |
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Institution: | Université de Strasbourg, Institut de Chimie - UMR 7177, Strasbourg Cedex, France |
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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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Keywords: | carvone hydroxysteroids Diels– Alder reactions enantioselectivity parallel kinetic resolution |
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