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

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

© 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 fluor...

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Main Authors: Teerachai Punirun, Darunee Soorukram, Chutima Kuhakarn, Vichai Reutrakul, Manat Pohmakotr
Other Authors: Mahidol University
Format: Article
Published: 2018
Subjects:
Chemistry
Online Access:https://repository.li.mahidol.ac.th/handle/123456789/35738
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spelling th-mahidol.357382018-11-23T16:55:53Z Stereoselective Synthesis of 1-Fluoro-exo,exo-2,6-diaryl-3,7-dioxabicyclo[3.3.0]octanes: Synthesis of (±)-1-Fluoromembrine Teerachai Punirun Darunee Soorukram Chutima Kuhakarn Vichai Reutrakul Manat Pohmakotr Mahidol University Chemistry © 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. 2018-11-23T09:55:53Z 2018-11-23T09:55:53Z 2015-08-21 Article Journal of Organic Chemistry. Vol.80, No.16 (2015), 7946-7960 10.1021/acs.joc.5b00970 15206904 00223263 2-s2.0-84939818413 https://repository.li.mahidol.ac.th/handle/123456789/35738 Mahidol University SCOPUS https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=84939818413&origin=inward
institution Mahidol University
building Mahidol University Library
continent Asia
country Thailand
Thailand
content_provider Mahidol University Library
collection Mahidol University Institutional Repository
topic Chemistry
spellingShingle Chemistry
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
description © 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.
author2 Mahidol University
author_facet Mahidol University
Teerachai Punirun
Darunee Soorukram
Chutima Kuhakarn
Vichai Reutrakul
Manat Pohmakotr
format Article
author Teerachai Punirun
Darunee Soorukram
Chutima Kuhakarn
Vichai Reutrakul
Manat Pohmakotr
author_sort Teerachai Punirun
title Stereoselective Synthesis of 1-Fluoro-exo,exo-2,6-diaryl-3,7-dioxabicyclo[3.3.0]octanes: Synthesis of (±)-1-Fluoromembrine
title_short Stereoselective Synthesis of 1-Fluoro-exo,exo-2,6-diaryl-3,7-dioxabicyclo[3.3.0]octanes: Synthesis of (±)-1-Fluoromembrine
title_full Stereoselective Synthesis of 1-Fluoro-exo,exo-2,6-diaryl-3,7-dioxabicyclo[3.3.0]octanes: Synthesis of (±)-1-Fluoromembrine
title_fullStr Stereoselective Synthesis of 1-Fluoro-exo,exo-2,6-diaryl-3,7-dioxabicyclo[3.3.0]octanes: Synthesis of (±)-1-Fluoromembrine
title_full_unstemmed Stereoselective Synthesis of 1-Fluoro-exo,exo-2,6-diaryl-3,7-dioxabicyclo[3.3.0]octanes: Synthesis of (±)-1-Fluoromembrine
title_sort stereoselective synthesis of 1-fluoro-exo,exo-2,6-diaryl-3,7-dioxabicyclo[3.3.0]octanes: synthesis of (±)-1-fluoromembrine
publishDate 2018
url https://repository.li.mahidol.ac.th/handle/123456789/35738
_version_ 1763497086263754752

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