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Biomimetic Synthesis of 5,6-dihydro-glaucogenin C: Construction of the Disecopregnane Skeleton by Iron(II)-Promoted Fragmentation of an α-Alkoxy Hydroperoxide

Authors

  • Jinghan Gui,

    1. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China), Fax: (+86) 21-5492-5176
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  • Dr. Dahai Wang,

    1. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China), Fax: (+86) 21-5492-5176
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  • Prof. Dr. Weisheng Tian

    Corresponding author
    1. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China), Fax: (+86) 21-5492-5176
    • Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China), Fax: (+86) 21-5492-5176
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Abstract

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Radikale Lösung: Eine biomimetische Synthese der natürlichen Titelverbindung gelang in 19 Stufen mit 6.4 % Gesamtausbeute. Die Eisen(II)-vermittelte Fragmentierung eines α-Alkoxyhydroperoxids mit anschließendem Abfangen des resultierenden tertiären Kohlenstoffradikals durch Iod führte dabei zu dem anspruchsvollen 13,14:14,15-Disecopregnan-Gerüst (siehe Schema; TBDPS=tert-Butyldiphenylsilyl).

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