A novel and efficient total synthesis of shikonin
A novel and efficient total synthesis of shikonin
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一种新颖高效的紫草素全合成方法
DOI：
10.1016/j.tetlet.2012.05.078
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发表时间：
2012-08-01
影响因子：
1.8
通讯作者：
Li, Shaoshun
中科院分区：
文献类型：
--
作者：
Wang, Rubing;Guo, Hui;Li, Shaoshun
报道了一种新颖有效的紫草素合成方法，该方法仅经六步反应，对映体过量（99.3%ee），总收率（47%）。该合成策略涉及有效的Ru（II）催化的不对称氢化，采用C-2-对称的平面手性二茂膦基恶唑啉配体（L-3），随后去除甲基保护基。同时，初步证实了紫草素的手性侧链很难同时具有立体选择性和α-区域选择性一步构建。(C)2012爱思唯尔有限公司保留所有权利。
A novel and efficient synthesis of shikonin was accomplished with excellent enantiomeric excess (99.3% ee) and high overall yield (47%) in only six steps. The synthetic strategy involved an efficient Ru(II)-catalyzed asymmetric hydrogenation employing C-2-symmetric planar chiral ruthenocene phosphinooxazoline ligand (L-3), followed by the subsequent removal of the methyl protecting groups. Meanwhile, it could be preliminarily confirmed that the chiral side chain of shikonin was difficult to be constructed in one step with both stereoselectivity and alpha-regioselectivity. (C) 2012 Elsevier Ltd. All rights reserved.