Systematic synthesis of diastereomeric THF ring cores and total synthesis of anti-tumor annonaceous acetogenins
Systematic synthesis of diastereomeric THF ring cores and total synthesis of anti-tumor annonaceous acetogenins
复制标题
DOI：
10.1055/s-2006-939688
复制
发表时间：
2006-05-03
期刊：
影响因子：
2
通讯作者：
Tanaka, Tetsuaki
中科院分区：
文献类型：
--
作者：
Maezaki, Naoyoshi;Kojima, Naoto;Tanaka, Tetsuaki
我们已经开发了一个系统的合成的多-THF环核心的抗肿瘤番荔枝内酯，通过利用不对称炔基化和随后的立体分散的THF环的形成作为关键步骤。α-羟基醛和α-四烯丙基呋喃醛与（S）-3-丁炔-1，2-二醇衍生物的不对称炔基化反应以良好的产率和非常高的非对映选择性进行。这些加合物通过两种不同的方法转化成单-和双-THF核，包括一锅THF环形成。应用该方法完成了对人肿瘤细胞具有细胞毒活性的murisolin、16，19-cis-murisolin和longimicin D的全合成。
We have developed a systematic synthesis of the poly-THF ring cores of anti-tumor Annonaceous acetogenins by utilizing asymmetric alkynylation and subsequent stereodivergent THF ring formation as key steps. The asymmetric alkynylation of alpha-oxyaldehyde and alpha-tetrallydrofuranic aldehyde with an (S)-3-butyne-1,2diol derivative proceeded in good yield with very high diastereo-selectivity. These adducts were converted into rnono- and bis-THF cores by two different methods involving one-pot THF ring formation. The total syntheses of murisolin, 16,19-cis-murisolin, and longimicin D, which show cytotoxic activity against the human tumor cell, were accomplished by applying this methodology.