A novel total synthesis of aculeatin A via a stepwise approach

A novel total synthesis of aculeatin A via a stepwise approach
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一种新型的一步法全合成aculeatin A

DOI:
10.1039/c6ra27140e
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发表时间:
2017-01
期刊:
影响因子:
3.9
通讯作者:
Wang Xiaoji
Wang Xiaoji
中科院分区:
化学3区
文献类型:
--
作者:
Zhang Zhibin;Leng Xiao;Yang Shenkun;Liang Cheng;Huang Shuangping;Wang Xiaoji

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Aculeatin A是从针叶砂仁中分离得到的一种具有抗疟疾活性的双环化合物。本文介绍了一种以1-十四醛为原料,经九步反应合成针叶乙素A的新方法。该方法的主要特点包括酮和酰氯的Claisen缩合、环脱水和分子内氧-迈克尔加成反应合成2,3-二氢-4H-吡喃-4-酮。
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.
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