A new synthesis of alkaloid (S)??3??hydroxypiperidin??2??one and its O??TBS protected derivative

PQ Huang, G Chen, X Zheng

文献索引：Huang, Pei-Qiang; Chen, Guo; Zheng, Xiao Journal of Heterocyclic Chemistry, 2007 , vol. 44, # 2 p. 499 - 501

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被引用次数: 7

摘要

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.