Practical syntheses of 4-fluoroprolines

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• 作者：Mukund S. Chorghade ; Debendra K. Mohapatra ; Gokarneswar Sahoo ; Mukund K. Gurjar ; Manish V. M ; lecha ; Nitin Bhoite ; Santosh Moghe ; Ronald T. Raines
• 关键词：Collagen ; 4-Fluoroproline ; 4-Hydroxyproline ; Nonnatural amino acid ; Process-scale synthesis
• 刊名：Journal of Fluorine Chemistry
• 出版年：2008
• 出版时间：September 2008
• 年：2008
• 卷：129
• 期：9
• 页码：781-784
• 全文大小：250 K

文摘

4-Fluoroprolines are among the most useful nonnatural amino acids in chemical biology. Here, practical routes are reported for the synthesis of the 2S,4R, 2S,4S, and 2R,4S diastereomers of 4-fluoroproline. Each route starts with (2S,4R)-4-hydroxyproline, which is a prevalent component of collagen and hence readily available, and uses a fluoride salt to install the fluoro group. Hence, the routes provide process-scale access to these useful nonnatural amino acids.