An efficient synthesis of pironetins employing a useful chiral building block, (1S, 5S, 6R)-5-hydroxybicyclo [4.1.0]heptan-2-one

Article abstract of DOI:10.1016/S0040-4020(99)00556-6

A convergent total synthesis of pironetin 1 and related compound 2 using a chiral building block, (IS, 5S, 6R)-5-hydroxybicyclo[4.1.0]heptan-2-one 5 is described. Both the dithiane 47 and the epoxide 32 with proper substituents were employed as coupling partners to construct the whole carbon skeleton 48, which was converted to (-)-pironetin 1 and (-)-2 in few steps. The usefulness of 5 for polyketide synthesis was demonstrated.