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First Synthesis of (+)-2,14-Deoxyalatol from -Santonin

First Synthesis of (+)-2,14-Deoxyalatol from α-Santonin

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【作者】 夏吾炯孙良东史雷张书宇涂永强

【Author】 XIA, Wu-Jiong SUN, Liang-Dong SHI, Lei ZHANG, Shu-Yu TU, Yong-Qiang* Department of Chemistry & State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China

【机构】 Department of Chemistry & State Key Laboratory of Applied Organic ChemistryLanzhou UniversityLanzhou University LanzhouGansu 730000ChinaLanzhouChina

【Abstract】 A novel and general approach for synthesis of the multi-oxygenated dihydrofuran sesquiterpenes has been de-veloped starting from santonin. The key steps involve: the strategic acid-catalyzed double-bond shifting affording 4, the novel base-promoted epoxide rearrangement of 5 generating two key functionals (the C5-OH and the D7,11 dou-ble bond), and the stereoselective cyclization of tetrahydrofuran ring without pre-controlling the stereochemistry of C-7. As an example of this approach, synthesis of (+)-2,14-deoxyalatol was described in detail.

【基金】 theNationalNaturalScienceFoundationofChina(Nos.29925205;30271488;20021001and203900501).
  • 【文献出处】 Chinese Journal of Chemistry ,中国化学(英文版) , 编辑部邮箱 ,2004年04期
  • 【分类号】O621
  • 【下载频次】8
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