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

摘要

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.