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Paper | Special issue | Vol 90, No. 2, 2015, pp.1082-1093
Published online, 14th August, 2014
DOI: 10.3987/COM-14-S(K)77
Investigation of Pd(II)-Catalyzed Cyclization of Chiral θ-Hydroxy-α,β,γ,δ-unsaturated Dienol

Akiko Ida, Naoyuki Hoshiya, and Jun'ichi Uenishi*

*Pharmacetuical Chemistry, Kyoto Pharmaceutical University, 1 Shichono-cho, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan


PdCl2(MeCN)2 catalyzed intramolecular cyclization of optically pure θ–hydroxyl-α,β,γ,δ−dienylethanols 1 and 2 are described. cis and trans-2- Benzyloxymethyl-6-(1,3-pentadienyl)tetrahydropyrans 3 and 4 were produced stereoselectively with a ratio of 3:1 in excellent yield. No 1,5-chirality transfer was observed in the cyclization reaction.