A Chiral Pool and Cross Metathesis Based Synthesis of Gingerdiols
A Chiral Pool and Cross Metathesis Based Synthesis of Gingerdiols
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基于手性池和交叉复分解的姜二醇合成
DOI：
10.1002/ejoc.201301727
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发表时间：
2014-04
影响因子：
2.8
通讯作者：
Li Yan
中科院分区：
文献类型：
--
作者：
Wan Zhi-Li;Zhang Guo-Liang;Chen Hui-Jun;Wu Yikang;Li Yan
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.
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DOI：
10.3891/acta.chem.scand.34b-0161
发表时间：
1980
期刊：
Acta Chemica Scandinavica
影响因子：
--
作者：
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通讯作者：
J. Gierer;O. Lindeberg;K. Daasvatn;J. Krane;H. Glaumann
影响因子：
6.7
作者：
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通讯作者：
D. K. Reddy;V. Shekhar;P. Prabhakar;B. Chinna Babu;B. Siddhardha;U. S. N. Murthy;Y. Venkateswarlu
影响因子：
--
作者：
J. Yadav;S. Das;A. Mishra
通讯作者：
J. Yadav;S. Das;A. Mishra
影响因子：
1.7
作者：
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通讯作者：
T. Murata;M. Shinohara;M. Miyamoto
DOI：
10.1055/s-2008-1067089
发表时间：
2008-05
期刊：
Synthesis
影响因子：
--
作者：
J. Yadav;Veerjala Naveen Kumar;R. Rao;P. Srihari
通讯作者：
J. Yadav;Veerjala Naveen Kumar;R. Rao;P. Srihari