A Chiral Pool and Cross Metathesis Based Synthesis of Gingerdiols

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	A Chiral Pool and Cross Metathesis Based Synthesis of Gingerdiols
	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
刊名	Eur. J. Org. Chem.
	2014
卷号	2014 期号:10 页码:2128-2139
其他题名	姜二醇的一种基于手性元-烯碳互换反应的合成
通讯作者	伍贻康 ; 李焰
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.
学科主题	有机化学
收录类别	SCI
原文出处	http://dx.doi.org/10.1002/ejoc.201301727
语种	英语
内容类型	期刊论文
源URL	[http://ir.sioc.ac.cn/handle/331003/38941]
专题	上海有机化学研究所_生命有机化学国家重点实验室
作者单位	1.湖北大学 2.中科院上海有机化学研究所
推荐引用方式 GB/T 7714	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.
APA	万致力,张国梁,陈慧君,伍贻康,&李焰.(2014).A Chiral Pool and Cross Metathesis Based Synthesis of Gingerdiols.Eur. J. Org. Chem.,2014(10),2128-2139.
MLA	万致力,et al."A Chiral Pool and Cross Metathesis Based Synthesis of Gingerdiols".Eur. J. Org. Chem. 2014.10(2014):2128-2139.