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    Please use this identifier to cite or link to this item: http://ir.cnu.edu.tw/handle/310902800/24243

    標題: One-Pot Ethynylation and Catalytic Desilylation in Synthesis of Mestranol and Levonorgestrel
    作者: Wen-Che Tseng
    Shih Hsien Chuang
    Yu-Hsiang Lin
    Shao-Kai Lin
    Jiann-Jyh Huang
    Fung Fuh Wong
    日期: 2011
    上傳時間: 2011-06-23 14:57:30 (UTC+8)
    摘要: A-pot ethylnylation and catalytic desilylation reaction was developed for the synthesis of mestranol and levonorgestrel. Addition of trimethylsilylacetylide to the carbonyl group at C-17 of the steroids yielded the C-17a-trimethylsilylacetylenyl adducts, which were desilylated with a catalytic amount of TBAF (0.050 equiv) in one pot to provide the corresponding mestranol and levonorgestrel both in 90% yields. A plausible mechanism was proposed for the catalytic desilylation through regeneration of the fluoride ion from the reaction of alkoxide on the steroid with Me3SiF. The one-pot ethynylation and catalytic desilylation methodology provided an alternative route and avoided the traditional use of flammable and explosive acetylene toward the synthesis 01 mestranoi ana levonorgestrel.
    Appears in Collections:[藥理學院] 2011年台俄有機、藥物與生物化學交流暨藥物化學研討會

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