镍（0）催化烯炔-环氧化合物还原偶联反应在（-）-cyatha-3,12-二烯合成中的策略性应用
Strategic use of nickel(0)-catalyzed enyne-epoxide reductive coupling towards the synthesis of (-)-cyatha-3,12-diene.
作者信息
Sparling Brian A, Simpson Graham L, Jamison Timothy F
机构信息
Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139, USA.
出版信息
Tetrahedron. 2009 Apr 18;65(16):3270-3280. doi: 10.1016/j.tet.2008.11.086.
Abstract
Various situations are explored in which the nickel(0)-catalyzed enyne-epoxide reductive coupling was utilized to access key intermediates towards the total synthesis of (-)-cyatha-3,12-diene (1). Enantioenriched 3,5-dien-1-ols with a variety of functionality were obtained in a straightforward manner from easily accessible 1,3-enynes and terminal epoxides.
摘要
研究了各种情况，其中利用镍(0)催化的烯炔-环氧化合物还原偶联反应来获得关键中间体，以用于(-)-杯伞-3,12-二烯(1)的全合成。通过简便的方法，从易于获得的1,3-烯炔和末端环氧化合物直接得到了具有多种官能团的对映体富集的3,5-二烯-1-醇。
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Strategic use of nickel(0)-catalyzed enyne-epoxide reductive coupling towards the synthesis of (-)-cyatha-3,12-diene.镍（0）催化烯炔-环氧化合物还原偶联反应在（-）-cyatha-3,12-二烯合成中的策略性应用
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Chem Commun (Camb). 2008 Mar 21(11):1347-9. doi: 10.1039/b717261c. Epub 2008 Jan 21.
2
Biomimetic total synthesis of (-)-erinacine E.（-）-海兔毒素E的仿生全合成。
J Am Chem Soc. 2008 Jan 30;130(4):1150-1. doi: 10.1021/ja7102795. Epub 2008 Jan 9.
3
Regioselectivity and enantioselectivity in nickel-catalysed reductive coupling reactions of alkynes.镍催化炔烃还原偶联反应中的区域选择性和对映选择性。
Chem Commun (Camb). 2007 Nov 21(43):4441-9. doi: 10.1039/b707737h. Epub 2007 Jul 3.
4
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J Org Chem. 2007 Sep 14;72(19):7451-4. doi: 10.1021/jo071132e. Epub 2007 Aug 14.
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Enantioselective total synthesis of cyathin A3.细胞松弛素A3的对映选择性全合成。
Org Lett. 2007 Jul 19;9(15):2843-6. doi: 10.1021/ol070994z. Epub 2007 Jun 20.
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