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Stereoselective synthesis of 13Z retinoic acids via β-methylenealdehydes as synthons |
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| 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. |
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