Publication: Synthesis of gem -difluoromethylenated polycyclic cage compounds
Issued Date
2015-02-06
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ISSN
15206904
00223263
00223263
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2-s2.0-84922719394
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Mahidol University
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SCOPUS
Bibliographic Citation
Journal of Organic Chemistry. Vol.80, No.3 (2015), 1577-1592
Suggested Citation
Chonticha Masusai, Darunee Soorukram, Chutima Kuhakarn, Patoomratana Tuchinda, Chaveng Pakawatchai, Saowanit Saithong, Vichai Reutrakul, Manat Pohmakotr Synthesis of gem -difluoromethylenated polycyclic cage compounds. Journal of Organic Chemistry. Vol.80, No.3 (2015), 1577-1592. doi:10.1021/jo502501v Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/35758
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Title
Synthesis of gem -difluoromethylenated polycyclic cage compounds
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Abstract
© 2015 American Chemical Society. The synthesis of gem-difluoromethylenated polycyclic cage compounds, utilizing PhSCF2SiMe3 as a gem-difluoromethylene building block, is described. The fluoride-catalyzed nucleophilic addition of PhSCF2SiMe3 to both maleic anhydride-cyclopentadiene and maleic anhydride-cyclohexadiene adducts was accomplished with high stereoselectivity to provide the corresponding adducts that were treated with Grignard reagents, followed by acid-catalyzed lactonization to afford the corresponding γ-butyrolactones, each as a single isomer. These γ-butyrolactones underwent intramolecular radical cyclization to give the corresponding tetracyclic cage γ-butyrolactones, which were employed as precursors for the synthesis of gem-difluoromethylenated tetracyclic cage lactols or tetracyclic cage furans, upon treatment with Grignard reagents.