Synthesis of an artificial HMG-CoA reductase inhibitor NK-104 via a hydrosilylation-cross-coupling reaction

Article abstract of DOI:10.1246/bcsj.68.2649

The hydrosilylation of t-butyl (3R,5S)-3,5-isopropylidenedioxy-6-heptynoate with ClMe₂SiH and a platinum catalyst, t-Bu₃P·Pt(CH₂ = CHSiMe₂)₂O, gave an (E)-vinylsilane in high yield with high regioselectivity. A subsequent cross-coupling reaction with an aryl halide afforded t-butyl (3R,5S,6E)-7-aryl-3,5-isopropylidene-dioxy-6-heptenoate. This sequence was applied to the synthesis of a potent HMC-CoA reductase inhibitor, NK-104.