One-pot facile conversion of Baylis-Hillman adduct into N-alkyl 3-(E)-alkylidene-5-substituted sulfonylpiperidine-2,6-dione.: Formal synthesis of tacamonine

被引：13
作者：
Chen, CY
Chang, MY [1 ]
Hsu, RT
Chen, ST
Chang, NC
机构：
[1] Natl Sun Yat Sen Univ, Dept Chem, Kaohsiung 804, Taiwan
[2] Natl Univ Kaohsiung, Dept Appl Chem, Kaohsiung 811, Taiwan
[3] Acad Sinica, Inst Biol Chem, Taipei 115, Taiwan
来源：
TETRAHEDRON LETTERS | 2003年 / 44卷 / 47期
关键词：
stepwise [3+3] strategy; Baylis-Hillman reaction; glutarimide; tacamonine;
D O I：
10.1016/j.tetlet.2003.08.053
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A stepwise [3+3] strategy to N-alkyl 3-(E)-alkylidene-5-substituted sulfonylpiperidine-2,6-dione 1 used various N-alkyl a-substituted sulfonylacetamides 2 and alpha,beta-unsaturated esters 3 as starting materials. alpha,beta-Unsaturated esters 3 were generated by Baylis-Hillman reaction. A ring closure mechanism was proposed for the reactions. This method provides a convenient formal synthesis of tacamonine. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码：8627 / 8630
页数：4
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