Total Synthesis of Quinolizidine (-)-217A
Total Synthesis of Quinolizidine (-)-217A
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DOI：
10.1021/jo101668k
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发表时间：
2010-11-19
影响因子：
3.6
通讯作者：
Mouries-Mansuy, Virginie
中科院分区：
文献类型：
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作者：
Fellah, Mouloud;Santarem, Marco;Mouries-Mansuy, Virginie
我们在此报道了通过还原胺化序列对合适的官能化哌啶进行分子内环化来构建喹诺里西啶环系统。该反应在 C4 处进行完全立体控制。哌啶前体的制备基于通过醛醇缩合或维蒂希反应对哌啶醛进行链延长。我们将第二种路线应用于从 (S)-甲基全合成喹诺里西啶 (-)-217A 2-((S)-1-((R)-1-苯乙基)哌啶-2-基)丙酸酯 5
We report here the construction of quinolizidine ring systems by intramolecular cyclization of suitable functionalized pipendines via a reductive amination sequence This reaction proceeds with a total stereocontrol at C4 The preparation of the piperidine precursors is based on a chain elongation of a piperidine aldehyde either by aldolization or by Wittig reaction We applied this second route to the total synthesis of quinolizidine (-)-217A from (S)-methyl 2-((S)-1-((R)-1-phenylethyl)pipendin-2-yl)propanoate 5