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    Title: One-Pot Ethynylation and Catalytic Desilylation in Synthesis of Mestranol and Levonorgestrel
    Authors: Wen-Che Tseng
    Shih Hsien Chuang
    Yu-Hsiang Lin
    Shao-Kai Lin
    Jiann-Jyh Huang
    Fung Fuh Wong
    Date: 2011
    Issue Date: 2011-06-23 14:57:30 (UTC+8)
    Abstract: 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:[Pharmacy and Science] 2011 Taiwanese-Russian Organic, Medicinal and Bio Chemistry Interactions & PST Medicinal Chemistry Symposium

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