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 |
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Authors: | PVeeraraghavan Ramachandran Kamlesh J Padiya Vivek Rauniyar MVenkat Ram Reddy Herbert C Brown |
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Institution: | Department of Chemistry, Herbert. C. Brown Center for Borane Research, Purdue University, 560 Oval Drive, West Lafayette, IN 47907-2084, USA |
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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. |
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Keywords: | Pentafluorobenzaldehyde α-Pinene &ldquo Allyl&rdquo boranes Ring-closing metathesis Hydrogenation Epoxidation Reduction |
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