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

doi:10.1016/j.jfluchem.2004.01.005

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 journal › Article › peer-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 language	English (US)
Pages (from-to)	615-620
Number of pages	6
Journal	Journal of Fluorine Chemistry
Volume	125
Issue number	4
DOIs	https://doi.org/10.1016/j.jfluchem.2004.01.005
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

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Ramachandran, P. V., Padiya, K. J., Rauniyar, V., Reddy, M. V. R., & Brown, H. C. (2004). 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. Journal of Fluorine Chemistry, 125(4), 615-620. https://doi.org/10.1016/j.jfluchem.2004.01.005

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. / Ramachandran, P. Veeraraghavan; Padiya, Kamlesh J.; Rauniyar, Vivek et al.
In: Journal of Fluorine Chemistry, Vol. 125, No. 4, 04.2004, p. 615-620.

Research output: Contribution to journal › Article › peer-review

Ramachandran, PV, Padiya, KJ, Rauniyar, V, Reddy, MVR & Brown, HC 2004, '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', Journal of Fluorine Chemistry, vol. 125, no. 4, pp. 615-620. https://doi.org/10.1016/j.jfluchem.2004.01.005

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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

Abstract

Bibliographical note

Keywords

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