金催化促进的瑞香烷/大戟烷三环核心的快速合成
Gold Catalysis-Facilitated Rapid Synthesis of the Daphnane/Tigliane Tricyclic Core.
作者信息
Li Yong, Wei Mufeng, Dai Mingji
机构信息
Department of Chemistry and Center for Cancer Research, Purdue University, West Lafayette, Indiana, IN 47907, United States.
Department of Chemistry, Tsinghua University, Beijing, 100084, China.
出版信息
Tetrahedron. 2017 Jul 20;73(29):4172-4177. doi: 10.1016/j.tet.2016.11.005. Epub 2016 Nov 3.
Abstract
A concise approach to synthesize the 5-7-6 tricyclic carbon skeleton of the daphnane/tigliane diterpene natural products has been accomplished a sequential gold-catalyzed furan formation and furan-allene [4+3] cycloaddition. This work provides new avenues for rapid and diverted synthesis of the medicinally important daphnane/tigliane diterpenes and their unnatural analogues.
摘要
通过金催化的呋喃形成和呋喃-丙二烯[4+3]环加成的顺序反应，已经实现了一种简洁的方法来合成瑞香烷/大戟烷二萜天然产物的5-7-6三环碳骨架。这项工作为快速且多样化地合成具有重要药用价值的瑞香烷/大戟烷二萜及其非天然类似物提供了新途径。
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本文引用的文献
1
Diastereocontrol in the Synthesis of Models of Rings C and D of Phorbol: Directing Effect of an Ether Substituent on Lithium Carbenoid Mediated Cyclopropanation.
Angew Chem Int Ed Engl. 2001 Jun 18;40(12):2311-2313. doi: 10.1002/1521-3773(20010618)40:12<2311::AID-ANIE2311>3.0.CO;2-T.
2
Concise, Enantioselective, and Versatile Synthesis of (-)-Englerin A Based on a Platinum-Catalyzed [4C+3C] Cycloaddition of Allenedienes.基于铂催化的[4C+3C]环加成反应，简洁、对映选择性和多功能合成(-)-岩白菜素 A。
Angew Chem Int Ed Engl. 2016 Nov 7;55(46):14359-14363. doi: 10.1002/anie.201607348. Epub 2016 Oct 13.
3
Nineteen-step total synthesis of (+)-phorbol.（+）-佛波醇的十九步全合成
Nature. 2016 Apr 7;532(7597):90-3. doi: 10.1038/nature17153. Epub 2016 Mar 23.
4
Gold catalysis in total synthesis - recent achievements.金催化在全合成中的应用——最新进展。
Chem Soc Rev. 2016 Mar 7;45(5):1331-67. doi: 10.1039/c5cs00721f.
5
Total Synthesis of Crotophorbolone.克罗托波醇的全合成。
Angew Chem Int Ed Engl. 2015 Nov 23;54(48):14457-61. doi: 10.1002/anie.201509160. Epub 2015 Oct 23.
6
Synthesis of the Tricyclic Ring Structure of Daphnanes via Intramolecular [4 + 3] Cycloaddition/SmI2-Pinacol Coupling.通过分子内[4+3]环加成/SmI2-频哪醇偶联合成达普那烷三环结构。
Org Lett. 2015 Jun 5;17(11):2672-5. doi: 10.1021/acs.orglett.5b01054. Epub 2015 May 21.
7
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Chem Soc Rev. 2014 May 7;43(9):2904-15. doi: 10.1039/c4cs00024b. Epub 2014 Mar 18.
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