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A novel total synthesis of aculeatin A via a stepwise approach†
RSC Advances ( IF 3.9 ) Pub Date : 2017-02-02 00:00:00 , DOI: 10.1039/c6ra27140e Zhibin Zhang 1, 2, 3, 4 , Xiao Leng 2, 3, 4, 5 , Shenkun Yang 1, 2, 3, 4 , Cheng Liang 1, 2, 3, 4 , Shuangping Huang 1, 2, 3, 4 , Xiaoji Wang 2, 3, 4, 6
RSC Advances ( IF 3.9 ) Pub Date : 2017-02-02 00:00:00 , DOI: 10.1039/c6ra27140e Zhibin Zhang 1, 2, 3, 4 , Xiao Leng 2, 3, 4, 5 , Shenkun Yang 1, 2, 3, 4 , Cheng Liang 1, 2, 3, 4 , Shuangping Huang 1, 2, 3, 4 , Xiaoji Wang 2, 3, 4, 6
Affiliation
Aculeatin A, isolated from the plant Amomum aculeatum, is a dispirocyclic compound having antimalarial activity. In this paper, we describe a novel synthetic approach to aculeatin A from 1-tetradecanal in nine steps via a stepwise strategy. The key features of this approach include the 1,3-diketone preparation from Claisen condensation of ketone and acyl chloride, cyclodehydration, and intramolecular oxa-Michael addition to 2,3-dihydro-4H-pyran-4-one.
中文翻译:
通过逐步的方法, 新的aculeatin A的全合成†
从植物砂仁中分离出的Aculeatin A是一种具有抗疟疾活性的双螺环化合物。在本文中,我们通过一种逐步策略,描述了一种从九-步骤中从1-十四烷中合成aculeatin A的新颖方法。该方法的关键特征包括由Claisen的酮与酰氯的Claisen缩合制备1,3-二酮,进行环脱水作用,以及向2,3-dihydro-4 H -pyran-4-one中添加分子内的oxa-Michael 。
更新日期:2017-02-02
中文翻译:
通过逐步的方法, 新的aculeatin A的全合成†
从植物砂仁中分离出的Aculeatin A是一种具有抗疟疾活性的双螺环化合物。在本文中,我们通过一种逐步策略,描述了一种从九-步骤中从1-十四烷中合成aculeatin A的新颖方法。该方法的关键特征包括由Claisen的酮与酰氯的Claisen缩合制备1,3-二酮,进行环脱水作用,以及向2,3-dihydro-4 H -pyran-4-one中添加分子内的oxa-Michael 。