Abstract
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.
Original language | English (US) |
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Pages (from-to) | 615-620 |
Number of pages | 6 |
Journal | Journal of Fluorine Chemistry |
Volume | 125 |
Issue number | 4 |
DOIs | |
State | Published - Apr 2004 |
Externally published | Yes |
Bibliographical note
Funding Information:Financial support from the Herbert C. Brown Center for Borane Research [19] and Aldrich Chemical Company is greatly acknowledged.
Keywords
- "Allyl"boranes
- Epoxidation
- Hydrogenation
- Pentafluorobenzaldehyde
- Reduction
- Ring-closing metathesis
- α-Pinene