Synthesis and Structural Revision of Phomopsin B, a Novel Polyketide Carrying a 10-Membered Cyclic-Ether Ring
Synthesis and Structural Revision of Phomopsin B, a Novel Polyketide Carrying a 10-Membered Cyclic-Ether Ring
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DOI：
10.1021/ol2011117
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发表时间：
2011-07-01
期刊：
影响因子：
5.2
通讯作者：
Takahashi, Shunya
中科院分区：
文献类型：
--
作者：
Izuchi, Yuko;Koshino, Hiroyuki;Takahashi, Shunya
通过分子内的烯烃歧化反应作为关键步骤，实现了所提出的结构2的全合成。然而，光谱数据与报道的天然产物的光谱数据不匹配。通过对已报道的核磁共振数据的重新检查，得到了已知的多硫瑞酮A 18的结构。多硫瑞酮A的R构型是通过与手性烯烃19的交叉歧化反应通过全合成确定的。
Total synthesis of the proposed structure 2 for phomopsin B was achieved by using an intramolecular olefin metathesis as a key step. The spectral data, however, did not match with those of the natural product reported. Re-examination of the reported NMR data led to the structural revision of phomopsin B to known dothiorelone A 18. The R configuration of dothiorelone A was determined by total synthesis through a cross-metathesis with a chiral olefin 19.