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Stereoselective synthesis of 13Z retinoic acids via β-methylenealdehydes as synthons
Authors:Alain Valla  Zo Andriamialisoa  Michel Giraud  Virginie Prat  Alain Laurent  Pierre Potier
Institution:

aChimie et Biologie de Substances Actives, UMR 175 associée au CNRS et au MNHN, 6, rue de l'Université 29000, Quimper, France

bInstitut de Chimie des Substances Naturelles, UPR 2301, CNRS, Avenue de la terrasse 91198, Gif-sur-Yvette, France

Abstract:A stereoselective synthesis of 13Z retinoic acids via β-methylenealdehydes is described. In methylene-de-oxo-bisubstitution reactions (Knoevenagel, Stobbe, etc.), these new synthons produce stereoselectively E olefins. Hence, a synthesis of 13Z retinoic acids is described, via a stereospecific monodecarboxylation of carboxy-14-retinoic acids.
Keywords:
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