Total Synthesis of Murisolins and Evaluation of Tumor‐Growth Inhibitory Activity.
Total Synthesis of Murisolins and Evaluation of Tumor‐Growth Inhibitory Activity.
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Murisolins 的全合成和肿瘤生长抑制活性的评价。
DOI：
10.1002/chin.200615211
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发表时间：
2006
期刊：
影响因子：
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通讯作者：
T. Yamori
中科院分区：
文献类型：
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作者：
N. Maezaki;Hiroaki Tominaga;N. Kojima;Minori Yanai;D. Urabe;R. Ueki;Tetsuaki Tanaka;T. Yamori
以α-四氢呋喃醛为原料，通过二炔的不对称炔基化反应和Sonogashira与γ-内酯的偶联反应，实现了murisolin（1）、天然16，19-cis-murisolin 2和非天然16，19-cis-murisolin 3的收敛全合成。合成了高光学纯度的α-四氢呋喃醛的立体异构体，并以较高的产率和高的非对映选择性进行了它们与1，6-庚二炔的不对称炔基化反应。还研究了合成化合物1 - 3的细胞生长抑制特征和比较分析。
Convergent total syntheses of murisolin (1), natural 16,19‐cis‐murisolin2, and unnatural 16,19‐cis‐murisolin3were accomplished by asymmetric alkynylation of α‐tetrahydrofuranic aldehyde with a diyne and Sonogashira coupling with a γ‐lactone segment as the key steps. Stereoisomers of α‐tetrahydrofuranic aldehyde were synthesized with high optical purity and the asymmetric alkynylation of these with 1,6‐heptadiyne proceeded in good yield and with high diastereoselectivity. The cell‐growth inhibition profile and COMPARE analysis of the synthetic compounds1–3were also investigated.