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通过级联环化进行亲电芳香异戊烯基化反应。

Electrophilic aromatic prenylation via cascade cyclization.

作者信息

Kodet John G, Topczewski Joseph J, Gardner Kevyn D, Wiemer David F

机构信息

Department of Chemistry, University of Iowa, Iowa City, Iowa 52242-1294 USA.

出版信息

Tetrahedron. 2013 Oct 4;69(44):9212-9218. doi: 10.1016/j.tet.2013.08.056.

DOI:10.1016/j.tet.2013.08.056
PMID:24610962
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3940164/
Abstract

To gain access to prenylated hexahydroxanthenes, tandem cascade cyclization-electrophilic aromatic substitution reactions have been studied on substrates bearing allylic and propargylic substituents. Both BF·OEt and TMSOTf can be used to initiate this reaction sequence, resulting in different ratios of the C-2 and C-6 substitution products. Even though allylic transposition is observed in some cases, the results of a crossover experiment are consistent with an intramolecular reaction sequence. Taken together, these studies now allow preparation of either the C-2 or C-6 prenylated hexahydroxanthene products.

摘要

为了获得异戊烯基化的六氢呫吨，已对带有烯丙基和炔丙基取代基的底物进行了串联级联环化-亲电芳香取代反应研究。BF·OEt和TMSOTf均可用于引发该反应序列，从而得到不同比例的C-2和C-6取代产物。尽管在某些情况下观察到了烯丙基重排，但交叉实验的结果与分子内反应序列一致。综上所述，这些研究现在使得制备C-2或C-6异戊烯基化的六氢呫吨产物成为可能。

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本文引用的文献

1
Α-mangostin and gambogic acid as potential inhibitors of the p53-MDM2 interaction revealed by a yeast approach.酵母双杂交法筛选的 p53-MDM2 相互作用潜在抑制剂：倒捻子素和藤黄酸。
J Nat Prod. 2013 Apr 26;76(4):774-8. doi: 10.1021/np400049j. Epub 2013 Mar 29.
2
Exploration of cascade cyclizations terminated by tandem aromatic substitution: total synthesis of (+)-schweinfurthin A.级联环化反应的探索，通过串联芳香取代反应终止：（+）-schweinfurthin A 的全合成。
J Org Chem. 2011 Feb 4;76(3):909-19. doi: 10.1021/jo1022102. Epub 2011 Jan 12.
3
Proteasome-inhibitory and cytotoxic constituents of Garcinia lateriflora: absolute configuration of caged xanthones.斜叶藤黄的蛋白酶体抑制和细胞毒性成分：笼形呫吨酮的绝对构型
Tetrahedron. 2010 Jul 17;66(29):5311-5320. doi: 10.1016/j.tet.2010.05.010.
4
Formal [4+3] epoxide cascade reaction via a complementary ambiphilic pairing strategy.通过互补的两性配对策略实现的[4+3]环氧化合物级联反应。
Org Lett. 2010 Mar 19;12(6):1216-9. doi: 10.1021/ol100035e.
5
Biomimetic total synthesis of tricycloillicinone and mechanistic studies toward the rearrangement of prenyl phenyl ethers.三环蒜藜芦碱酮的仿生全合成及异戊烯基苯基醚重排的机理研究
Tetrahedron Lett. 2008 Nov 3;49(45):6383-6385. doi: 10.1016/j.tetlet.2008.07.184.
6
A tandem cascade cyclization-electrophilic aromatic substitution: application in the total synthesis of (+)-angelichalcone.串联级联环化-亲电芳香取代反应：在（+）-当归根素全合成中的应用。
J Am Chem Soc. 2009 Oct 21;131(41):14630-1. doi: 10.1021/ja906468v.
7
Total synthesis of (+)-schweinfurthins B and E.(+)-schweinfurthins B 和 E 的全合成。
J Org Chem. 2009 Sep 18;74(18):6965-72. doi: 10.1021/jo901161m.
8
Biomimetic synthesis of dimeric metabolite acremine G via a highly regioselective and stereoselective Diels-Alder reaction.
Org Lett. 2009 Jul 16;11(14):2988-91. doi: 10.1021/ol901004e.
9
Selective isomerization of epoxides to allylic alcohols catalyzed by TiO2-supported gold nanoparticles.二氧化钛负载的金纳米颗粒催化环氧化物选择性异构化为烯丙醇
Angew Chem Int Ed Engl. 2009;48(17):3133-6. doi: 10.1002/anie.200805838.
10
Cytotoxic polyprenylated xanthones from the resin of Garcinia hanburyi.来自藤黄树脂的细胞毒性多异戊烯基呫吨酮
J Nat Prod. 2009 Jan;72(1):117-24. doi: 10.1021/np800460b.