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[摘要]：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-alpha-carbanion E via the lithium-naphthalenide (LN)-mediated reductive lithiation, capable of reacting with carbonyl compounds without an acidic alpha-proton to give the alpha-hydroxyalkylation products. |
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