title: Stereoselective Synthesis of 1-Fluoro-exo,exo-2,6-diaryl-3,7-dioxabicyclo[3.3.0]octanes: Synthesis of (±)-1-Fluoromembrine.
abstract: 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 LiAlH4 or 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.
authors.affiliation: Center of Excellence for Innovation in Chemistry (PERCH-CIC) and Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.
authors.forename: Teerachai
authors.initials: T
authors.lastname: Punirun
authors.affiliation: Center of Excellence for Innovation in Chemistry (PERCH-CIC) and Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.
authors.forename: Darunee
authors.initials: D
authors.lastname: Soorukram
authors.affiliation: Center of Excellence for Innovation in Chemistry (PERCH-CIC) and Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.
authors.forename: Chutima
authors.initials: C
authors.lastname: Kuhakarn
authors.affiliation: Center of Excellence for Innovation in Chemistry (PERCH-CIC) and Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.
authors.forename: Vichai
authors.initials: V
authors.lastname: Reutrakul
authors.affiliation: Center of Excellence for Innovation in Chemistry (PERCH-CIC) and Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.
authors.forename: Manat
authors.initials: M
authors.lastname: Pohmakotr
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry*; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: C000603245:1-fluoromembrine; D019086:Bridged Bicyclo Compounds, Heterocyclic; D005663:Furans