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A Chiral Pool and Cross Metathesis Based Synthesis of Gingerdiols
Alternative Title姜二醇的一种基于手性元-烯碳互换反应的合成
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
Source PublicationEur. J. Org. Chem.
AbstractBoth (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.
Subject Area有机化学
Indexed BySCI
Citation statistics
Cited Times:8[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Corresponding AuthorWu YK(伍贻康); Li Y(李焰)
Recommended Citation
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.
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