Convenient synthesis of substituted piperidinones from α,β-unsaturated amides:: Formal synthesis of deplancheine, tacamonine, and paroxetine

被引：54

作者：

Takasu, K ^{[1
]}

Nishida, N ^{[1
]}

Tomimura, A ^{[1
]}

Ihara, M ^{[1
]}

机构：

[1] Tohoku Univ, Grad sch Pharmaceut Sci, Dept Organ Chem, Sendai, Miyagi 9808578, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 10期

关键词：

D O I：

10.1021/jo050261x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An intermolecular aza-double Michael reaction leading to functionalized piperidin-2-ones from simple starting materials has been developed. The method allows alpha,beta-unsaturated amides to be used as a synthon of the piperidine nucleus. In addition, the utility of this methodology is demonstrated by its application to a formal synthesis of the indolo[2,3-a]quinolizidine alkaloids, (+/-)-deplancheine, (+/-)-tacamonine, and the antidepressant paroxetine.

引用

页码：3957 / 3962

页数：6

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[1] A TOTAL SYNTHESIS OF THE ALKALOID DEPLANCHEINE [J].