ENANTIOSELECTIVE ROUTE TO ARYL(1,3-BUTADIEN-2-YL)METHANOLS: FORMAL SYNTHESIS OF (-)-SPOROCHNOL A

Ti(IV)-promoted reaction of the chiral acetals derived from aromatic aldehydes with 1-(tri-n-butyl)stannyl-2,3-butadiene followed by removal of the chiral auxiliary gave aryl(1,3-butadien-2-yl)methanols with high enantiomeric purity (>90% ee). The synthetic utility of this method was demonstrated by the formal synthesis of (-)-sporochnol A, a terpene possessing a chiral benzylic quaternary carbon center.