Development of a new approach for the synthesis of (+)-15-deoxy-Δ^12,14-prostaglandin J₂ methyl ester based on the [2+2]-cycloadduct of 5-trimethylsilylcyclopentadiene and dichloroketene

Abstract

An asymmetric total synthesis of 15-deoxy-Δ12,14-prostaglandin J2 methyl ester is presented. The synthesis begins with the preparation of enantiopure (3aR,6R,6aS)-6-(trimethylsilyl)-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]furan-1-one by an optical resolution of [2+2]-cycloadduct of easily available 5-trimethylcyclopentadiene...