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Paper | Special issue | Vol 79, No. 1, 2009, pp.681-693
Published online, 21st November, 2008
DOI: 10.3987/COM-08-S(D)35
Facile Syntheses of Three Ahp-Type Building Blocks with Complementary Reactivity

Wen Chen, Xiao Zheng, Yuan-Ping Ruan, and Pei-Qiang Huang*

*Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, China

Abstract

Two protected 3-amino-6-hydroxy-2-piperidone derivatives (Ahp, 12 and 6), as well as a thioether analogue (7) were synthesized starting from L-glutamic acid in four, five, and six steps respectively. The Ahp derivatives 12 and 6 are not only the structural feature found in many naturally occurring bioactive depsipeptides, but also precursors of the N-acyliminium such as D; while the (S)-thioether 7 was shown to be an effective synthetic equivalent of the novel 2-piperidone N-α-carbanion E via the lithium-naphthalenide (LN)-mediated reductive lithiation, capable of reacting with carbonyl compounds without an acidic α–position to give the α-hydroxyalkylation products.