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

P. Veeraraghavan Ramachandran, Kamlesh J. Padiya, Vivek Rauniyar, M. Venkat Ram Reddy, Herbert C. Brown

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

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 languageEnglish (US)
Pages (from-to)615-620
Number of pages6
JournalJournal of Fluorine Chemistry
Volume125
Issue number4
DOIs
StatePublished - Apr 2004
Externally publishedYes

Bibliographical note

Funding Information:
Financial support from the Herbert C. Brown Center for Borane Research [19] and Aldrich Chemical Company is greatly acknowledged.

Copyright:
Copyright 2008 Elsevier B.V., All rights reserved.

Keywords

  • "Allyl"boranes
  • Epoxidation
  • Hydrogenation
  • Pentafluorobenzaldehyde
  • Reduction
  • Ring-closing metathesis
  • α-Pinene

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