title: Concise Approach to (ent)-14 β-Hydroxysteroids through Highly Diastereo-/Enantioselective Diels-Alder Reactions.
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.
authors.affiliation: Université de Strasbourg, Institut de Chimie - UMR 7177, 1 rue Blaise Pascal, BP296/R8-67008, Strasbourg Cedex, France.
authors.forename: Clovis
authors.initials: C
authors.lastname: Peter
authors.affiliation: Université de Strasbourg, Institut de Chimie - UMR 7177, 1 rue Blaise Pascal, BP296/R8-67008, Strasbourg Cedex, France.
authors.forename: Blandine
authors.initials: B
authors.lastname: Ressault
authors.affiliation: Université de Strasbourg, Institut de Chimie - UMR 7177, 1 rue Blaise Pascal, BP296/R8-67008, Strasbourg Cedex, France.
authors.forename: Philippe
authors.initials: P
authors.lastname: Geoffroy
authors.affiliation: Université de Strasbourg, Institut de Chimie - UMR 7177, 1 rue Blaise Pascal, BP296/R8-67008, Strasbourg Cedex, France. m.miesch@unistra.fr.
authors.forename: Michel
authors.initials: M
authors.lastname: Miesch
mesh_terms: D061565:Cycloaddition Reaction / Q000379:methods*; D006914:Hydroxysteroids / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D006914:Hydroxysteroids
keywords: Diels-Alder reactions; carvone; enantioselectivity; hydroxysteroids; parallel kinetic resolution