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A new synthesis of alkaloid (S)-3-hydroxypiperidin-2-one and its O-TBS protected derivative
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : March 2007 , DOI: 10.1002/jhet.5570440239 Pei-Qiang Huang , Guo Chen , Xiao Zheng
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : March 2007 , DOI: 10.1002/jhet.5570440239 Pei-Qiang Huang , Guo Chen , Xiao Zheng
From the known lactone (S)-4, easily derived from L-glutamic acid, a scalable approach to chiral building block O-silylated 3-hydroxypiperidin-2-one 3 and alkaloid 1 was achieved in five and six-steps respectively. The key steps are a chemoselective amidation of lactone-ester 5 and a one-pot reductive borane-decomplexation, N-debenzylation and cyclization.
中文翻译:
生物碱(S)-3-羟基哌啶-2-酮及其O - TBS保护衍生物的新合成
从容易衍生自L-谷氨酸的已知内酯(S)-4,分别通过五个步骤和六个步骤实现了可扩展的手性结构单元O-甲硅烷基化的3-羟基哌啶-2-酮3和生物碱1的方法。关键步骤是内酯5的化学选择性酰胺化反应以及一锅还原硼烷分解,N-脱苄基化和环化反应。
更新日期:2017-01-31
中文翻译:
生物碱(S)-3-羟基哌啶-2-酮及其O - TBS保护衍生物的新合成
从容易衍生自L-谷氨酸的已知内酯(S)-4,分别通过五个步骤和六个步骤实现了可扩展的手性结构单元O-甲硅烷基化的3-羟基哌啶-2-酮3和生物碱1的方法。关键步骤是内酯5的化学选择性酰胺化反应以及一锅还原硼烷分解,N-脱苄基化和环化反应。