Publication:
Stereoselective Synthesis of 1-Fluoro-exo,exo-2,6-diaryl-3,7-dioxabicyclo[3.3.0]octanes: Synthesis of (±)-1-Fluoromembrine

Issued Date

2015-08-21

Resource Type

Article

ISSN

15206904
00223263

DOI

10.1021/acs.joc.5b00970

Other identifier(s)

2-s2.0-84939818413

Rights

Mahidol University

Rights Holder(s)

SCOPUS

Bibliographic Citation

Journal of Organic Chemistry. Vol.80, No.16 (2015), 7946-7960

Suggested Citation

Teerachai Punirun, Darunee Soorukram, Chutima Kuhakarn, Vichai Reutrakul, Manat Pohmakotr Stereoselective Synthesis of 1-Fluoro-exo,exo-2,6-diaryl-3,7-dioxabicyclo[3.3.0]octanes: Synthesis of (±)-1-Fluoromembrine. Journal of Organic Chemistry. Vol.80, No.16 (2015), 7946-7960. doi:10.1021/acs.joc.5b00970 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/35738

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Title

Stereoselective Synthesis of 1-Fluoro-exo,exo-2,6-diaryl-3,7-dioxabicyclo[3.3.0]octanes: Synthesis of (±)-1-Fluoromembrine

Author(s)

Teerachai Punirun
 Darunee Soorukram
 Chutima Kuhakarn
 Vichai Reutrakul
 Manat Pohmakotr

Other Contributor(s)

Mahidol University

Abstract

© 2015 American Chemical Society. Stereoselective synthesis of 1-fluoro-exo,exo-2,6-diaryl-3,7-dioxabicyclo[3.3.0]octanes is described. The synthetic strategy involves stereoselective fluorination of 3,4-trans-4,5-cis-3-aroyl-5-arylparaconic esters using Selectfluor to afford the corresponding fluorinated paraconic esters in good yields as a single isomer, which are subjected to reduction employing LiAlH4or DIBALH followed by furofuran formation under acidic or Lewis acid conditions to afford a series of 1-fluoro-exo,exo-furofurans in moderate yields. The synthetic protocol also provides an access to (±)-1-fluoromembrine.

Keyword(s)

Chemistry

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URI

https://repository.li.mahidol.ac.th/handle/123456789/35738

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Scopus 2011-2015