Total synthesis and structure confirmation of the annonaceous acetogenins 30(S)-hydroxybullatacin, uvarigrandin a, and 5(R)-uvarigrandin a (narumicin I?).
Total synthesis and structure confirmation of the annonaceous acetogenins 30(S)-hydroxybullatacin, uvarigrandin a, and 5(R)-uvarigrandin a (narumicin I?).
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DOI：
10.1021/jo0266137
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发表时间：
2003-02
期刊：
影响因子：
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通讯作者：
J. Marshall;Arnaud Piettre;M. Paige;F. Valeriote
中科院分区：
文献类型：
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作者：
J. Marshall;Arnaud Piettre;M. Paige;F. Valeriote
本发明描述了通过应用先前公开的四组分模块化方法合成双四氢呋喃番荔枝内酯30(S)-羟基布拉他星、紫草甜素A和5(R)-紫草甜素A，其中延伸的核心片段偶联到C4-或C5-羟基丁烯内酯末端。丁烯内酯末端片段由(S)-或(R)-苹果酸制备。合成的30(S)-羟基布拉沙星和紫草甜素A及其Mosher酯衍生物的光谱性质与报道的天然物质的值非常一致。合成的5(R)-uvargrandin A可能与纳鲁米星I相同，但已报道的核磁共振谱中的细微差异阻碍了对这一点的明确评估。
A synthesis of the bistetrahydrofuran Annonaceous acetogenins 30(S)-hydroxybullatacin, uvarigrandin A, and 5(R)-uvarigrandin A through application of a previously disclosed four-component modular approach is described in which extended core segments are coupled to a C4- or C5-hydroxy butenolide terminus. The butenolide termini segments were prepared from (S)- or (R)-malic acid. Spectral properties of synthetic 30(S)-hydroxybullatacin and uvarigrandin A, as well as their Mosher ester derivatives, were in close agreement to the reported values for the natural substances. The synthetic 5(R)-uvarigrandin A is possibly identical to narumicin I, but subtle differences in the reported NMR spectra prevented an unambiguous assessment of this point.