Asymmetric "allyl"boration of pentafluorobenzaldehyde with various α-pinene based "allyl"boranes provides homoallylic alcohols in high de and ee; the alcohols have been converted into δ-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.
Bibliographical noteFunding Information:
Financial support from the Herbert C. Brown Center for Borane Research  and Aldrich Chemical Company is greatly acknowledged.
Copyright 2008 Elsevier B.V., All rights reserved.
- Ring-closing metathesis