Synthesis and Absolute Stereochemisty of a Cruciferous Phytoalexin, (−)-Spirobrassinin

Synthesis and Absolute Stereochemisty of a Cruciferous Phytoalexin, (−)-Spirobrassinin
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DOI:
10.1246/cl.2000.886
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发表时间:
2000-08
期刊:
影响因子:
1.6
通讯作者:
K. Monde;S. Ōsawa;N. Harada;M. Takasugi;M. Suchý;P. Kutschy;M. Dzurilla;E. Balentová
K. Monde;S. Ōsawa;N. Harada;M. Takasugi;M. Suchý;P. Kutschy;M. Dzurilla;E. Balentová
中科院分区:
化学4区
文献类型:
--
作者:
K. Monde;S. Ōsawa;N. Harada;M. Takasugi;M. Suchý;P. Kutschy;M. Dzurilla;E. Balentová

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合成的(±)-螺油菜素(1)通过手性辅助法拆分得到(+)-1和天然的(−)-1。(+)-1的(1‘-S,4’R)-龙脑酰衍生物的绝对构型由X-射线晶体学确证。因此,Natural(−)-1具有S构型。他们的CD光谱支持这一结果。
Synthetic (±)-spirobrassinin (1) was enantioresolved by a chiral auxiliary method giving (+)-1 and natural (−)-1. The absolute configuration was unambiguously determined by X-ray crystallography of a (1′S,4′R)-camphanoyl derivative of (+)-1. Consequently, natural (−)-1 has an S configuration. Their CD spectra supported this result.