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Communication | Special issue | Vol 77, No. 1, 2009, pp.249-253
Published online, 28th August, 2008
DOI: 10.3987/COM-08-S(F)58
Enantioselective Route to Aryl(1,3-butadien-2-yl)methanols: Formal Synthesis of (-)-Sporochnol A

Daisuke Yanagimoto, Kazuyuki Kawano, Keisuke Takahashi, Jun Ishihara, and Susumi Hatakeyama*

*Department of Pharmaceutical Sciences, Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan

Abstract

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.