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A convergent total synthesis of pironetin1 and related compound2 using a chiral building block,(1S,5S,6R)-5-hydroxybicyclo[4.1.0]heptan-2-one5 is described. Both the dithiane47 and the epoxide32 with proper substituents were employed as coupling partners to construct the whole carbon skeleton48, which was converted to (−)-pironetin1 and (−)-2 in few steps. The usefulness of5 for polyketide synthesis was demonstrated.
Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan
Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan
Department of Chemical Synthesis Drugs Safety Res. Center Tokushima Res. Inst., Otsuka Pharmaceutical Co., Ltd., 463-10 Kagasuno, Kawauchi-cho, Tokushima 771-0130, Japan
Department of Chemical Synthesis Drugs Safety Res. Center Tokushima Res. Inst., Otsuka Pharmaceutical Co., Ltd., 463-10 Kagasuno, Kawauchi-cho, Tokushima 771-0130, Japan