First total synthesis of longimicin D
First total synthesis of longimicin D
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DOI：
10.1002/ejoc.200500850
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发表时间：
2006-03
影响因子：
2.8
通讯作者：
Hiroaki Tominaga;N. Maezaki;Minori Yanai;N. Kojima;D. Urabe;R. Ueki;Tetsuaki Tanaka
中科院分区：
文献类型：
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作者：
Hiroaki Tominaga;N. Maezaki;Minori Yanai;N. Kojima;D. Urabe;R. Ueki;Tetsuaki Tanaka
我们首次完成了长米星 D (1) 的全合成，它对人胰腺癌细胞表现出有效的细胞毒性。带有拥挤立体中心的双 THF 核心是通过我们的聚 THF 核心合成方法构建的，该方法包括 C4 单元的不对称炔基化和立体发散的 THF 环形成。尽管我们计划加入 C9-C34 双 THF 核心片段 2 和 C1-C8 γ-内酯片段 3，但模型研究表明耦合很困难。我们通过将双 THF 醛 24 与代表从 C3 到 C12 位的多亚甲基链的官能化炔 19 进行不对称炔基化来解决这个问题。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 德国, 2006)
We have accomplished the first total synthesis of longimicin D (1), which displays potent cytotoxicity against human pancreatic carcinoma cells. The bis-THF core bearing congested stereocenters was constructed by our methodology for synthesis of poly-THF cores, which consists of asymmetric alkynylation with the C4 unit and stereodivergent THF ring formation. Although we had planned to join the C9–C34 bis-THF core segment 2 and the C1–C8 γ-lactone segment 3, a model study revealed that the coupling was difficult. We resolved the problem by applying asymmetric alkynylation of bis-THF aldehyde 24 with functionalized alkyne 19 respresenting the polymethylene chain from the C3 to C12 position. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)