对映选择性全合成及 (+)-kibdelone A 和四羟基蒽酮类似物的生物评价。
Enantioselective total synthesis and biological evaluation of (+)-kibdelone A and a tetrahydroxanthone analogue.
机构信息
Department of Chemistry, Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
出版信息
J Org Chem. 2013 Aug 2;78(15):7617-26. doi: 10.1021/jo401169z. Epub 2013 Jul 23.
Abstract
The total synthesis of kibdelone A has been accomplished via In(III)-catalyzed arylation of a heterocyclic quinone monoketal and iodine-mediated oxidative photochemical electrocyclization for construction of the ABCD ring moiety. Enzymatic dihydroxylation of methyl 2-halobenzoate substrates was employed for synthesis of activated 2-halo-cyclohexene F-ring fragments. A one pot oxa-Michael/Friedel-Crafts process allowed access to the first simplified DEF ring analogues of the kibdelones.
摘要
通过 In(III)催化的杂环醌单缩酮的芳基化反应和碘介导的氧化光电化学环化反应，实现了 kibdelone A 的全合成，构建了 ABCD 环部分。采用酶促二羟基化甲基 2-卤代苯甲酸酯底物合成了活化的 2-卤代环己烯 F 环片段。一锅法的氧杂-Michael/Friedel-Crafts 过程可以得到 kibdelones 的第一个简化的 DEF 环类似物。
相似文献
1
Enantioselective total synthesis and biological evaluation of (+)-kibdelone A and a tetrahydroxanthone analogue.对映选择性全合成及 (+)-kibdelone A 和四羟基蒽酮类似物的生物评价。
J Org Chem. 2013 Aug 2;78(15):7617-26. doi: 10.1021/jo401169z. Epub 2013 Jul 23.
2
Enantioselective total synthesis of (-)-kibdelone C.对（-）-kibdelone C 的对映选择性全合成。
J Am Chem Soc. 2011 Jul 6;133(26):9956-9. doi: 10.1021/ja204040k. Epub 2011 Jun 15.
3
Synthesis and biological evaluation of ABCD ring fragments of the kibdelones.奇放线菌素ABCD环片段的合成及生物学评价
Angew Chem Int Ed Engl. 2011 Mar 7;50(11):2511-5. doi: 10.1002/anie.201007613. Epub 2011 Feb 18.
4
Organocatalytic enantioselective formal arylation of azlactones using quinones as the aromatic partner.以醌类作为芳香反应底物，通过有机催化实现恶唑烷酮的对映选择性形式芳基化反应。
Chem Commun (Camb). 2015 Jun 30;51(56):11280-2. doi: 10.1039/c5cc03677a.
5
Diversity Oriented Synthesis of Novel Xanthones Reveal Potent Doxorubicin-Inspired Analogs.新型黄烷酮的多样性导向合成揭示了具有强大多柔比星启发的类似物。
ChemMedChem. 2024 May 2;19(9):e202400055. doi: 10.1002/cmdc.202400055. Epub 2024 Feb 29.
6
Oxiranylmethyloxy or thiiranylmethyloxy-azaxanthones and -acridone analogues as potential topoisomerase I inhibitors.氧杂环丁烷甲基氧基或硫杂环丁烷甲基氧基-氮杂蒽酮和吖啶酮类似物作为潜在的拓扑异构酶 I 抑制剂。
Bioorg Med Chem Lett. 2009 Dec 1;19(23):6766-9. doi: 10.1016/j.bmcl.2009.09.091. Epub 2009 Sep 27.
7
Total synthesis and absolute stereochemical assignment of kibdelone C.kibdelone C 的全合成与绝对立体化学构型确定。
J Am Chem Soc. 2011 Jul 6;133(26):9952-5. doi: 10.1021/ja203642n. Epub 2011 Jun 15.
8
Evaluation of the pharmacophoric motif of the caged Garcinia xanthones.笼状藤黄素药效团模式评估。
Org Biomol Chem. 2009 Dec 7;7(23):4886-94. doi: 10.1039/b913496d. Epub 2009 Sep 24.
9
Tetrahydroxanthones by sequential Pd-catalyzed C-O and C-C bond construction and use in the identification of the "antiausterity" pharmacophore of the kigamicins.通过顺序 Pd 催化的 C-O 和 C-C 键构建得到四羟基蒽酮，并用于鉴定 kigamicins 的“抗紧缩”药效团。
Org Lett. 2011 Mar 4;13(5):1056-9. doi: 10.1021/ol103103n. Epub 2011 Jan 26.
10
Synthesis and antitumor activity evaluation of a novel series of xanthone derivatives.新型氧杂蒽酮衍生物系列的合成及抗肿瘤活性评价
J Asian Nat Prod Res. 2015;17(4):377-83. doi: 10.1080/10286020.2014.1003048. Epub 2015 Jan 28.
引用本文的文献
1
Naturally Occurring Organohalogen Compounds-A Comprehensive Review.天然有机卤代化合物综述。
Prog Chem Org Nat Prod. 2023;121:1-546. doi: 10.1007/978-3-031-26629-4_1.
2
Applications of Friedel-Crafts reactions in total synthesis of natural products.傅-克反应在天然产物全合成中的应用。
RSC Adv. 2018 Dec 3;8(70):40061-40163. doi: 10.1039/c8ra07325b. eCollection 2018 Nov 28.
3
Assembly of multicyclic isoquinoline scaffolds from pyridines: formal total synthesis of fredericamycin A.由吡啶构建多环异喹啉骨架：弗雷德里卡霉素A的形式全合成
Chem Sci. 2021 Jun 28;12(30):10259-10265. doi: 10.1039/d1sc02442f. eCollection 2021 Aug 4.
4
The Synthesis of Conjugated Bis-Aryl Vinyl Substrates and Their Photoelectrocyclization Reactions towards Phenanthrene Derivatives.共轭双芳基乙烯基底物的合成及其向菲衍生物的光电子环化反应。
Synthesis (Stuttg). 2021;53(7):1200-1212. doi: 10.1055/s-0040-1706001. Epub 2021 Jan 11.
5
Benefits of Unconventional Methods in the Total Synthesis of Natural Products.非传统方法在天然产物全合成中的益处。
ACS Omega. 2018 Dec 31;3(12):17326-17340. doi: 10.1021/acsomega.8b02994. Epub 2018 Dec 14.
6
Synthesis and Biological Evaluation of Kibdelone C and Its Simplified Derivatives.Kibdelone C 及其简化衍生物的合成与生物评价。
J Am Chem Soc. 2016 Aug 24;138(33):10561-70. doi: 10.1021/jacs.6b05484. Epub 2016 Aug 9.
7
Synthesis of o-chlorophenols via an unexpected nucleophilic chlorination of quinone monoketals mediated by N,N'-dimethylhydrazine dihydrochloride.通过由盐酸N,N'-二甲基肼介导的醌单缩酮意外亲核氯化反应合成邻氯酚。
Org Biomol Chem. 2014 May 14;12(18):2854-8. doi: 10.1039/c4ob00391h.
本文引用的文献
1
Polycyclic xanthone natural products: structure, biological activity and chemical synthesis.多环酮类天然产物：结构、生物活性与化学合成。
Nat Prod Rep. 2013 Mar;30(3):382-91. doi: 10.1039/c3np20122h. Epub 2013 Jan 21.
2
Toward a visible light mediated photocyclization: Cu-based sensitizers for the synthesis of [5]helicene.可见光促进光环化反应：基于铜的敏化剂用于[5]螺旋芳烃的合成。
Org Lett. 2012 Jun 15;14(12):2988-91. doi: 10.1021/ol300983b. Epub 2012 May 29.
3
Xanthones from fungi, lichens, and bacteria: the natural products and their synthesis.来自真菌、地衣和细菌的氧杂蒽酮：天然产物及其合成。
Chem Rev. 2012 Jul 11;112(7):3717-76. doi: 10.1021/cr100446h. Epub 2012 May 22.
4
Toluene dioxygenase mediated oxidation of halogen-substituted benzoate esters.甲苯双加氧酶介导的卤代苯甲酸酯的氧化。
Org Biomol Chem. 2012 Jun 14;10(22):4407-16. doi: 10.1039/c2ob25202c. Epub 2012 May 4.
5
Enantioselective total synthesis of (-)-kibdelone C.对（-）-kibdelone C 的对映选择性全合成。
J Am Chem Soc. 2011 Jul 6;133(26):9956-9. doi: 10.1021/ja204040k. Epub 2011 Jun 15.
6
Total synthesis and absolute stereochemical assignment of kibdelone C.kibdelone C 的全合成与绝对立体化学构型确定。
J Am Chem Soc. 2011 Jul 6;133(26):9952-5. doi: 10.1021/ja203642n. Epub 2011 Jun 15.
7
Coupling of quinone monoacetals promoted by sandwiched Brønsted acids: synthesis of oxygenated biaryls.夹心布朗斯特酸促进的醌单缩醛偶联反应：含氧联芳基的合成
Angew Chem Int Ed Engl. 2011 Jun 27;50(27):6142-6. doi: 10.1002/anie.201101646. Epub 2011 May 23.
8
Synthesis and biological evaluation of ABCD ring fragments of the kibdelones.奇放线菌素ABCD环片段的合成及生物学评价
Angew Chem Int Ed Engl. 2011 Mar 7;50(11):2511-5. doi: 10.1002/anie.201007613. Epub 2011 Feb 18.
9
Tetrahydroxanthones by sequential Pd-catalyzed C-O and C-C bond construction and use in the identification of the "antiausterity" pharmacophore of the kigamicins.通过顺序 Pd 催化的 C-O 和 C-C 键构建得到四羟基蒽酮，并用于鉴定 kigamicins 的“抗紧缩”药效团。
Org Lett. 2011 Mar 4;13(5):1056-9. doi: 10.1021/ol103103n. Epub 2011 Jan 26.
10
Cationic iron-catalyzed intramolecular alkyne-hydroarylation with electron-deficient arenes.阳离子铁催化的缺电子芳环与炔烃的分子内芳基化反应。
Chem Commun (Camb). 2010 Mar 14;46(10):1748-50. doi: 10.1039/b920695g. Epub 2010 Jan 12.
Zotero 插件