Total synthesis of (±)-bruguierol A via an intramolecular [3+2] cycloaddition of cyclopropane 1,1-diester
Total synthesis of (±)-bruguierol A via an intramolecular [3+2] cycloaddition of cyclopropane 1,1-diester
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DOI：
10.1016/j.tet.2010.05.057
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发表时间：
2010-07-24
期刊：
影响因子：
2.1
通讯作者：
Wang, Zhongwen
中科院分区：
文献类型：
--
作者：
Hu, Bao;Xing, Siyang;Wang, Zhongwen
天然产物（+/-）-bruguierol A经10步全合成，总收率16.8%。该天然产物中嵌入的独特的8-氧杂双环[3.2.1]辛烷核心骨架是通过本实验室最近开发的新型Sc（OTf）（3）催化的环丙烷分子内[3+2]环加成反应构建的。这种通用的合成策略可以潜在地应用于合成广泛的结构相关的天然产物。(C)2010爱思唯尔有限公司保留所有权利。
Total synthesis of natural product (+/-)-bruguierol A was accomplished in 10-steps and with an overall 16.8% yield. The embedded unique 8-oxabicyclo[3.2.1]octane core skeleton in this natural product was constructed via a novel Sc(OTf)(3)-catalyzed intramolecular [3+2] cycloaddition of cyclopropane, which was developed recently in this laboratory. This general synthetic strategy can be potentially applied to the synthesis of a broad range of structurally related natural products. (C) 2010 Elsevier Ltd. All rights reserved.