Synthesis of non-proteinogenic amino acids using Michael addition to unsaturated orthopyroglutamate derivative

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• 作者：Makoto Oba ; Tsuneki Saegusa ; Naohiro Nishiyama ; Kozaburo Nishiyama
• 关键词：Amino acids ; Pyroglutaminol ; Michael addition ; ABO ester
• 刊名：Tetrahedron
• 出版年：2009
• 出版时间：3 January 2009
• 年：2009
• 卷：65
• 期：1
• 页码：128-133
• 全文大小：251 K

文摘

Stereoselective synthesis of non-proteinogenic amino acids via Michael addition to 3,4-didehydropyroglutamate derivative in which the carboxyl function is protected as a 2,7,8-trioxabicyclo[3.2.1]octane (ABO ester) group is described. The obtained 3-substituted pyroglutamic ABO ester was directly converted to 3-substituted glutamic acids such as chlorpheg by acidic hydrolysis, whereas 3-substituted proline derivatives were obtained by chemoselective reduction of the lactam carbonyl group. A formal total synthesis of baclofen, a γ-aminobutyric acid (GABA) analogue, is also described.