Asymmetric synthesis of 6-(2′,3′,4′,5′,6′-pentafluorophenyl)-δ-lactones via "allyl"boranes:: application for the synthesis of fluorinated analog of key pharmacophore of statin drugs

Asymmetric "allyl"boration of pentafluorobenzaldehyde with various alpha-pinene based "allyl"boranes provides homoallylic alcohols in high de and ee; the alcohols have been converted into delta-lactones via acryloylation, ring-closing metathesis and hydrogenation. Pentafluorophenyl analog of key pharmacophore of statin drugs has been synthesized using diastereoselective epoxidation and regioselective reduction as key steps. (C) 2004 Elsevier B.V. All rights reserved.