异叶茴芹不规则二萜类化合物绝对构型的测定：圆二色光谱和核磁共振方法的应用
Determination of the absolute configuration of Anisotome irregular diterpenes: application of CD and NMR methods.
作者信息
Van Klink John W, Baek Seung-Hwa, Barlow Anna J, Ishii Hideki, Nakanishi Koji, Berova Nina, Perry Nigel B, Weavers Rex T
机构信息
Crop and Food Research, Department of Chemistry, Otago University, Dunedin, New Zealand.
出版信息
Chirality. 2004 Oct;16(8):549-58. doi: 10.1002/chir.20074.
Several Anisotome diterpene derivatives were synthesized in an attempt to obtain a crystalline compound for X-ray analysis. Although we were unable to obtain a suitable crystal, the absolute configuration of the irregular diterpene skeleton was determined using two other techniques: a circular dichroism (CD) protocol based on a tetraarylporphyrin molecular tweezer that allowed prediction of the absolute stereochemistry on a microscale level, and a method employing differences in NMR shifts from derivatization of the naturally occurring acid 1 with enantiomers of a phenylglycine methyl ester (PGME) chiral anisotropic reagent. The excellent agreement between the CD and NMR methods led to the assignment of a 2S-absolute configuration for anisotomenoic acid 1.
为了获得用于X射线分析的晶体化合物，合成了几种异叶苣苔二萜衍生物。尽管我们未能获得合适的晶体，但使用另外两种技术确定了不规则二萜骨架的绝对构型：一种基于四芳基卟啉分子镊子的圆二色性（CD）方法，该方法能够在微观尺度上预测绝对立体化学；另一种方法是利用天然存在的酸1与苯基甘氨酸甲酯（PGME）手性各向异性试剂的对映体衍生化产生的NMR位移差异。CD方法和NMR方法之间的出色一致性使得异叶苣苔酸1的绝对构型被确定为2S。
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