SYNTHESES EN SERIE RACEMIQUE ET EN SERIE OPTIQUEMENT ACTIVE D'UNE FAMILLE DE DERIVES OXYGENES NATURELS DE L'OMBELLIFERONE. STRUCTURE SPATIALE DU (-)EPOXY-3',6' AURAPTENE.

Article abstract of DOI:10.1016/S0040-4020(01)85097-3

3',6'-Epoxyaurapten and marmin were synthesized by a stereocontrolled way in racemic then in optically active forms from a chiral precursors.The synthetic strategy is of biomimetic type.The reaction sequence involved a Sharpless asymmetric epoxydation as the key-step to induce chirality.E nantiomeric conversion gave rise to the opposite unnatural serie.The structural dimensions of (-)3'6'-epoxyaurapten have been ascertained by means of X-ray cristallography.This route allows the preparation of related molecules.