盖宝灵木生物碱 (-)-GB17 的全合成。
Total synthesis of the Galbulimima alkaloid (-)-GB17.
机构信息
Department of Chemistry, Northwestern University, 2145 Sheridan Rd, Evanston, IL 60208, USA.
出版信息
Angew Chem Int Ed Engl. 2012 Mar 5;51(10):2481-4. doi: 10.1002/anie.201108227. Epub 2012 Jan 27.
Abstract
The first enantioselective total synthesis of (−)-GB17 is reported. Construction of this unique naphthoquinolizinone skeleton was achieved by two stereoselective intramolecular Michael additions. The first of these Michael additions is controlled by the use of a chiral organocatalyst, while the second cyclization is under substrate control and proceeds with concomitant lactam formation.
摘要
首次报道了（-）-GB17 的对映选择性全合成。通过两个立体选择性的分子内迈克尔加成反应构建了这种独特的萘醌并里西啶骨架。第一个迈克尔加成反应由手性有机催化剂控制，而第二个环化反应受底物控制并伴随着内酰胺形成。
相似文献
1
Total synthesis of the Galbulimima alkaloid (-)-GB17.盖宝灵木生物碱 (-)-GB17 的全合成。
Angew Chem Int Ed Engl. 2012 Mar 5;51(10):2481-4. doi: 10.1002/anie.201108227. Epub 2012 Jan 27.
2
Total synthesis of 7'-desmethylkealiiquinone.7'-去甲基基拉烯醌的全合成。
Org Lett. 2012 May 4;14(9):2274-7. doi: 10.1021/ol300704w. Epub 2012 Apr 24.
3
Total Synthesis of the Galbulimima Alkaloids Himandravine and GB17 Using Biomimetic Diels-Alder Reactions of Double Diene Precursors.利用双烯前体的仿生狄尔斯-阿尔德反应全合成加布力米马生物碱喜马拉维宁和GB17
J Am Chem Soc. 2015 Sep 2;137(34):11197-204. doi: 10.1021/jacs.5b07710. Epub 2015 Aug 25.
4
Total synthesis of 7'-desmethylkealiiquinone, 4'-desmethoxykealiiquinone, and 2-deoxykealiiquinone.7'-去甲基基奎宁酮、4'-去甲氧基基奎宁酮和 2-脱氧基奎宁酮的全合成。
J Org Chem. 2014 Mar 21;79(6):2481-90. doi: 10.1021/jo4027337. Epub 2014 Mar 3.
5
Total syntheses and cytotoxicity of kealiiquinone, 2-deoxy-2-aminokealiiquinone and analogs.总合成与细胞毒性研究：基莱醌、2-脱氧-2-氨基基莱醌及类似物。
Bioorg Med Chem Lett. 2013 Nov 15;23(22):6183-7. doi: 10.1016/j.bmcl.2013.08.093. Epub 2013 Sep 6.
6
Synthesis and target annotation of the alkaloid GB18.生物碱 GB18 的合成及靶标注释。
Nature. 2022 Jun;606(7916):917-921. doi: 10.1038/s41586-022-04840-9. Epub 2022 May 12.
7
Extraction studies of Tabernanthe iboga and Voacanga africana.伊波加和非洲沃坎加的提取研究。
Nat Prod Lett. 2002 Feb;16(1):71-6. doi: 10.1080/1057563029001/4881.
8
Stereoselective synthesis of 2,6-disubstituted piperidines using the iridium-catalyzed allylic cyclization as configurational switch: asymmetric total synthesis of (+)-241 d and related piperidine alkaloids.以铱催化的烯丙基环化作为构型转换的2,6-二取代哌啶的立体选择性合成：(+)-241 d及相关哌啶生物碱的不对称全合成
Chemistry. 2009;15(9):2050-4. doi: 10.1002/chem.200802525.
9
Cyclopeptide alkaloids from Zizyphus sativa bark.来自枣属植物树皮的环肽生物碱。
Nat Prod Res. 2008 Feb 15;22(3):219-21. doi: 10.1080/14786410601133483.
10
Concise synthesis of heterocycle-fused naphthoquinones by employing sonogashira coupling and tandem addition-elimination/intramolecular cyclization.
Chem Pharm Bull (Tokyo). 2013;61(6):648-54. doi: 10.1248/cpb.c13-00102.
引用本文的文献
1
Synthesis of psychotropic alkaloids from .来自……的精神活性生物碱的合成
Tetrahedron. 2022 Nov 5;126. doi: 10.1016/j.tet.2022.133064. Epub 2022 Oct 5.
2
Structures of New Alkaloids from Rain Forest Trees and in Papua New Guinea, Indonesia, and Northern Australia.来自巴布亚新几内亚、印度尼西亚和澳大利亚北部雨林树木的新生物碱结构
ACS Omega. 2018 Feb 14;3(2):1912-1921. doi: 10.1021/acsomega.7b02065. eCollection 2018 Feb 28.
3
Concise Enantioselective Synthesis of Oxygenated Steroids via Sequential Copper(II)-Catalyzed Michael Addition/Intramolecular Aldol Cyclization Reactions.通过连续的铜（II）催化迈克尔加成/分子内羟醛环化反应对氧化甾体进行简洁的对映选择性合成。
J Am Chem Soc. 2015 Nov 18;137(45):14341-8. doi: 10.1021/jacs.5b08528. Epub 2015 Nov 10.
4
Total Synthesis of the Galbulimima Alkaloids Himandravine and GB17 Using Biomimetic Diels-Alder Reactions of Double Diene Precursors.利用双烯前体的仿生狄尔斯-阿尔德反应全合成加布力米马生物碱喜马拉维宁和GB17
J Am Chem Soc. 2015 Sep 2;137(34):11197-204. doi: 10.1021/jacs.5b07710. Epub 2015 Aug 25.
本文引用的文献
1
Enantioselective total synthesis and studies into the configurational stability of bismurrayaquinone A.对双木脂醌 A 的对映选择性全合成及构象稳定性研究。
Angew Chem Int Ed Engl. 2011 Oct 10;50(42):9931-4. doi: 10.1002/anie.201104726. Epub 2011 Sep 7.
2
11-Step enantioselective synthesis of (-)-lomaiviticin aglycon.11 步对映选择性合成(-)-洛马维亭苷元。
J Am Chem Soc. 2011 May 18;133(19):7260-3. doi: 10.1021/ja200034b. Epub 2011 Jan 31.
3
Synthetic studies toward galbulimima alkaloid (-)-GB 13 and (+)-GB 16 and (-)-himgaline.针对 galbulimima 生物碱 (-)-GB 13 和 (+)-GB 16 以及 (-)-himgaline 的合成研究。
Chem Asian J. 2011 Feb 1;6(2):573-9. doi: 10.1002/asia.201000556. Epub 2010 Dec 14.
4
A convergent route to the Galbulimima alkaloids (-)-GB 13 and (+)-GB 16.一条通往加布力马生物碱（-）-GB 13和（+）-GB 16的汇聚合成路线。
Angew Chem Int Ed Engl. 2010 Aug 9;49(34):5887-90. doi: 10.1002/anie.201002299.
5
Total synthesis of (+/-)- and (-)-actinophyllic acid.(+/-)-和(-)-actinophyllic 酸的全合成。
J Am Chem Soc. 2010 Apr 7;132(13):4894-906. doi: 10.1021/ja100178u.
6
Total synthesis of alkaloid (+/-)-G. B. 13 using a Rh(I)-catalyzed ketone hydroarylation and late-stage pyridine reduction.利用 Rh(I)催化的酮氢芳基化反应和晚期吡啶还原反应，全合成生物碱 (+/-)-G. B. 13。
J Am Chem Soc. 2009 Sep 23;131(37):13244-5. doi: 10.1021/ja9063487.
7
Development of a merged conjugate addition/oxidative coupling sequence. Application to the enantioselective total synthesis of metacycloprodigiosin and prodigiosin R1.一种合并的共轭加成/氧化偶联序列的开发。其在间环原放线菌素和原放线菌素R1的对映选择性全合成中的应用。
J Am Chem Soc. 2009 Oct 14;131(40):14579-83. doi: 10.1021/ja906122g.
8
Total synthesis of (-)-himandrine.（-）-海芒果碱的全合成。
J Am Chem Soc. 2009 Jul 22;131(28):9648-50. doi: 10.1021/ja903790y.
9
Intermolecular enolate heterocoupling: scope, mechanism, and application.分子间烯醇化物杂偶联：范围、机理及应用
J Am Chem Soc. 2008 Aug 27;130(34):11546-60. doi: 10.1021/ja804159y. Epub 2008 Aug 5.
10
Discovery of a novel, orally active himbacine-based thrombin receptor antagonist (SCH 530348) with potent antiplatelet activity.发现一种新型的、口服活性的基于辛可宁的凝血酶受体拮抗剂（SCH 530348），具有强效抗血小板活性。
J Med Chem. 2008 Jun 12;51(11):3061-4. doi: 10.1021/jm800180e. Epub 2008 May 1.
Zotero 插件