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学科主题: 有机化学
题名: A Chiral Pool and Cross Metathesis Based Synthesis of Gingerdiols
其他题名: 姜二醇的一种基于手性元-烯碳互换反应的合成
作者: Wan ZL(万致力)1; Zhang GL(张国梁)1; Chen HJ(陈慧君)1; Wu YK(伍贻康)1; Li Y(李焰)1
通讯作者: 伍贻康 ; 李焰
刊名: Eur. J. Org. Chem.
发表日期: 2014
DOI: 10.1002/ejoc.201301727
卷: 2014, 期:10, 页:2128-2139
收录类别: SCI
英文摘要: Both (3R,5S)- and (3R,5R)-gingerdiols were synthesized. Their 1,3-diol motifs were derived from enantiopure epoxy chiral building blocks that were readily accessible from D-gluconolactone. The effect of deuterating the OH groups of the natural isomer on its optical rotation was also examined. In the course of the syntheses of the targets, an unexplored cross-metathesis (CM) reaction of unprotected 5-substituted pent-1-ene-3,5-diols was investigated, in which the CM product readily underwent an allylic epimerization and oxidation, as the starting diols rearranged into ketones with unprecedented ease. These problems were eventually resolved by performing the CM reaction in toluene in the presence of phenol. The cause of these unexpected, yet very interesting phenomena, was determined to be the presence of the unprotected OH group at C-5 of the 5-substituted pent-1-ene-3,5-diol. A mechanistic rationale is also presented.
语种: 英语
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/38941
Appears in Collections:生命有机化学国家重点实验室_期刊论文

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作者单位: 1.湖北大学
2.中科院上海有机化学研究所

Recommended Citation:
Wan ZL,Zhang GL,Chen HJ,et al. A Chiral Pool and Cross Metathesis Based Synthesis of Gingerdiols[J]. Eur. J. Org. Chem.,2014,2014(10):2128-2139.
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