托沃菲林B的全合成。
Total Synthesis of Tovophyllin B.
作者信息
Jeso Valer, Nicolaou K C
机构信息
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, and Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92037, USA.
出版信息
Tetrahedron Lett. 2009 Mar 18;50(11):1161-1163. doi: 10.1016/j.tetlet.2008.12.096.
Abstract
The first total synthesis of tovophyllin B (2), an antimicrobial xanthone derived from mangosteen, has been accomplished through a convergent strategy from building blocks 6 and 7 involving lithium-mediated coupling, dehydrative cyclization, and 6π electrocyclization as key steps.
摘要
托沃菲林B（2）是一种源自山竹果的具有抗菌活性的呫吨酮，其首次全合成已通过一种汇聚策略由构建模块6和7完成，该策略涉及锂介导的偶联、脱水环化和6π电环化作为关键步骤。
相似文献
1
Total Synthesis of Tovophyllin B.托沃菲林B的全合成。
Tetrahedron Lett. 2009 Mar 18;50(11):1161-1163. doi: 10.1016/j.tetlet.2008.12.096.
2
Concise total synthesis of calothrixins A and B.Calothrixins A 和 B 的简洁全合成。
Org Lett. 2011 Jul 1;13(13):3356-9. doi: 10.1021/ol201107a. Epub 2011 May 31.
3
Application of a 6pi-1-azatriene electrocyclization strategy to the total synthesis of the marine sponge metabolite ageladine A and biological evaluation of synthetic analogues.6π-1-氮杂三烯电环化策略在海洋海绵代谢产物阿吉拉定A全合成中的应用及合成类似物的生物学评价
J Org Chem. 2007 Jun 22;72(13):4892-9. doi: 10.1021/jo0707232. Epub 2007 Jun 1.
4
A thermal 6pi electrocyclization strategy towards taiwaniaquinoids. First enantiospecific synthesis of (-)-taiwaniaquinone G.一种用于台湾杉醌类化合物的热6π电环化策略。（-）-台湾杉醌G的首次对映体特异性合成。
Chem Commun (Camb). 2009 Feb 7(5):592-4. doi: 10.1039/b816812a. Epub 2008 Dec 5.
5
A new total synthesis of the zinc matrixmetalloproteinase inhibitor ageladine A featuring a biogenetically patterned 6pi-2-azatriene electrocyclization.一种新的锌基质金属蛋白酶抑制剂阿吉拉汀A的全合成方法，其具有生物生源模式的6π-2-氮杂三烯电环化反应。
Org Lett. 2007 Mar 1;9(5):853-5. doi: 10.1021/ol063038a. Epub 2007 Jan 30.
6
Pyridone annulation via tandem Curtius rearrangement/6π-electrocyclization: total synthesis of (-)-lyconadin C.通过串联 Curtius 重排/6π-电环化反应实现吡啶酮环化：(-)-lyconadin C 的全合成。
Org Lett. 2013 Aug 16;15(16):4226-9. doi: 10.1021/ol401954f. Epub 2013 Aug 2.
7
Terminal Alkynes as One-Carbon Donors in [5+1] Heteroannulation: Synthesis of Pyridines via Ynimine Intermediates and Application in the Total Synthesis of Anibamine B.终端炔作为[5+1]杂环芳构化的一碳供体：通过亚胺中间体合成吡啶及其在阿尼巴宾 B 全合成中的应用。
Angew Chem Int Ed Engl. 2023 May 22;62(22):e202303537. doi: 10.1002/anie.202303537. Epub 2023 Apr 21.
8
Total Synthesis of Gastrodinol via Photocatalytic 6π Electrocyclization.通过光催化 6π 电环化反应的全合成 Gastrodinol。
Org Lett. 2020 Sep 4;22(17):6822-6826. doi: 10.1021/acs.orglett.0c02335. Epub 2020 Aug 24.
9
Convergent Synthesis of Kibdelone C.Kibdelone C 的汇聚合成。
Org Lett. 2018 May 18;20(10):2872-2875. doi: 10.1021/acs.orglett.8b00901. Epub 2018 May 8.
10
Asymmetric Total Synthesis of the Rearranged Steroid Phomarol Enabled by a Biomimetic S2' Cyclization.通过仿生S2'环化实现重排甾体化合物Phomarol的不对称全合成。
J Am Chem Soc. 2023 Apr 26;145(16):9354-9363. doi: 10.1021/jacs.3c02817. Epub 2023 Apr 12.
引用本文的文献
1
Ethyl 2-amino-4-(4-methyl-1,3-thia-zol-5-yl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carboxyl-ate.2-氨基-4-(4-甲基-1,3-噻唑-5-基)-5-氧代-4H,5H-吡喃并[3,2-c]色烯-3-羧酸乙酯
Acta Crystallogr Sect E Struct Rep Online. 2013 Aug 10;69(Pt 9):o1411-2. doi: 10.1107/S1600536813021703. eCollection 2013.
2
Total Syntheses of Proposed (±)-Trichodermatides B and C.拟（±）-木霉肽B和C的全合成
Tetrahedron Lett. 2013 Oct 9;54(41). doi: 10.1016/j.tetlet.2013.07.137.
3
Constructing the Architecturally Distinctive ABD-Tricycle of Phomactin A through an Intramolecular [3 + 3] Annulation Strategy.通过分子内[3 + 3]环化策略构建具有独特结构的福马菌素A的ABD-三轮车结构。
Tetrahedron. 2011 Dec 30;67(52):10105-10118. doi: 10.1016/j.tet.2011.09.111.
4
Ethyl 2-amino-4-(4-fluoro-phen-yl)-6-meth-oxy-4H-benzo[h]chromene-3-carboxyl-ate.2-氨基-4-（4-氟苯基）-6-甲氧基-4H-苯并[h]色烯-3-羧酸乙酯
Acta Crystallogr Sect E Struct Rep Online. 2012 Jun 1;68(Pt 6):o1803-4. doi: 10.1107/S1600536812021939. Epub 2012 May 19.
5
Total syntheses of graphisin A and sydowinin B.Graphisin A 和 Sydowinin B 的全合成。
Org Lett. 2012 Jun 1;14(11):2862-5. doi: 10.1021/ol301107m. Epub 2012 May 23.
6
Total synthesis of (±)-phomactin A. Lessons learned from respecting a challenging structural topology.（±）-phomactin A 的全合成。从尊重具有挑战性的结构拓扑中学到的经验教训。
J Org Chem. 2011 Sep 2;76(17):7027-39. doi: 10.1021/jo200936r. Epub 2011 Aug 5.
本文引用的文献
1
"Biomimetic" Cascade Reactions in Organic Synthesis: Construction of 4-Oxatricyclo[4.3.1.0]decan-2-one Systems and Total Synthesis of 1-O-Methylforbesione via Tandem Claisen Rearrangement/Diels-Alder Reactions.有机合成中的“仿生”级联反应：通过串联克莱森重排/狄尔斯-阿尔德反应构建4-氧杂三环[4.3.1.0]癸烷-2-酮体系及1-O-甲基福布斯酮的全合成
Angew Chem Int Ed Engl. 2001 Nov 19;40(22):4264-4268. doi: 10.1002/1521-3773(20011119)40:22<4264::AID-ANIE4264>3.0.CO;2-1.
2
Asymmetric total synthesis of B-ring modified (-)-epicatechin gallate analogues and their modulation of beta-lactam resistance in Staphylococcus aureus.B 环修饰的 (-)-表儿茶素没食子酸酯类似物的不对称全合成及其对金黄色葡萄球菌β-内酰胺抗性的调节作用
Tetrahedron. 2005 Aug 8;61(32):7703-7711. doi: 10.1016/j.tet.2005.05.086.
3
Biomimetic total synthesis of gambogin and rate acceleration of pericyclic reactions in aqueous media.藤黄菌素的仿生全合成及水相中周环反应的速率加速
Angew Chem Int Ed Engl. 2005 Jan 21;44(5):756-61. doi: 10.1002/anie.200462211.
4
Unified synthesis of caged Garcinia natural products based on a site-selective Claisen/Diels-Alder/Claisen rearrangement.基于位点选择性克莱森/狄尔斯-阿尔德/克莱森重排的笼状藤黄属天然产物的统一合成。
Proc Natl Acad Sci U S A. 2004 Aug 17;101(33):12030-5. doi: 10.1073/pnas.0401932101. Epub 2004 Jun 21.
5
Biomimetically inspired total synthesis and structure activity relationships of 1-O-methyllateriflorone. 6 pi electrocyclizations in organic synthesis.1-O-甲基侧花酮的仿生全合成及构效关系。有机合成中的6π电环化反应。
J Am Chem Soc. 2004 May 5;126(17):5493-501. doi: 10.1021/ja040037+.
6
Total synthesis of 1-O-methyllateriflorone.1-O-甲基侧花酮的全合成。
Angew Chem Int Ed Engl. 2003 Sep 15;42(35):4225-9. doi: 10.1002/anie.200351805.
7
Biological activities of alpha-mangostin derivatives against acidic sphingomyelinase.
Bioorg Med Chem Lett. 2003 Oct 6;13(19):3151-3. doi: 10.1016/s0960-894x(03)00719-4.
8
Antimycobacterial activity of prenylated xanthones from the fruits of Garcinia mangostana.山竹果实中异戊烯基氧杂蒽酮的抗分枝杆菌活性
Chem Pharm Bull (Tokyo). 2003 Jul;51(7):857-9. doi: 10.1248/cpb.51.857.
9
Effect of Calcium Reagents on Aldol Reactions of Phenolic Enolates with Aldehydes in Alcohol.钙试剂对酚烯醇盐与醛在醇中进行的羟醛反应的影响
J Org Chem. 1996 Oct 4;61(20):6768-6769. doi: 10.1021/jo961352k.
Zotero 插件