通过羟基导向胍基化的 (+)-瓜环酸的全合成。
Total Synthesis of (+)-Guadinomic Acid via Hydroxyl-Directed Guanidylation.
机构信息
Department of Chemistry and Biochemistry , University of California , Santa Barbara , California 93110 , United States.
出版信息
J Org Chem. 2018 Aug 17;83(16):9492-9496. doi: 10.1021/acs.joc.8b01214. Epub 2018 Jun 22.
Abstract
Protecting-group-free total synthesis of (+)-guadinomic acid is reported using δ-valerolactone as a readily available starting material. The protocol utilizes the recent hydroxyl-directed guanidylation of unactivated alkenes as an approach for direct stereoselective incorporation of the guanidine unit furnishing the natural product in 7 steps.
摘要
本文报道了一种使用 δ-戊内酯作为易得起始原料的、无保护基的（+）-瓜环酸的全合成方法。该方案利用最近报道的未活化烯烃的羟基导向胍基化反应作为直接立体选择性引入胍基单元的方法，以 7 步反应得到天然产物。
相似文献
1
Total Synthesis of (+)-Guadinomic Acid via Hydroxyl-Directed Guanidylation.通过羟基导向胍基化的 (+)-瓜环酸的全合成。
J Org Chem. 2018 Aug 17;83(16):9492-9496. doi: 10.1021/acs.joc.8b01214. Epub 2018 Jun 22.
2
Advances in catalytic and protecting-group-free total synthesis of natural products: a recent update.催化和无保护基全合成天然产物的最新进展综述。
Chem Commun (Camb). 2020 Aug 7;56(61):8569-8590. doi: 10.1039/d0cc02659j. Epub 2020 Jun 15.
3
2,2-Difunctionalization of alkenes via Pd(II)-catalyzed aza-Wacker reactions.通过 Pd(II)催化的氮杂 Wacker 反应实现烯烃的 2,2-双官能化。
Org Lett. 2011 Feb 18;13(4):728-31. doi: 10.1021/ol102956x. Epub 2011 Jan 18.
4
Stereodivergent synthesis of the LFA-1 antagonist BIRT-377 by porcine liver esterase desymmetrization and Curtius rearrangement.通过猪肝酯酶去对称化和库尔提斯重排立体发散合成LFA-1拮抗剂BIRT-377。
Org Biomol Chem. 2015 Feb 7;13(5):1463-9. doi: 10.1039/c4ob02303j.
5
Optical resolution of (+/-)-1,2-Bis(2-methylphenyl)ethylene-1,2-diamine as a chiral framework for 2-iminoimidazolidine with 2-methylphenyl pendant and the guanidine-catalyzed asymmetric michael reaction of tert-butyl diphenyliminoacetate and ethyl acrylate.将（±）-1,2-双（2-甲基苯基）乙烯-1,2-二胺作为带有2-甲基苯基侧基的2-亚氨基咪唑烷的手性骨架进行光学拆分，以及叔丁基二苯基亚氨基乙酸酯与丙烯酸乙酯的胍催化不对称迈克尔反应。
J Org Chem. 2008 Jan 4;73(1):133-41. doi: 10.1021/jo701923z. Epub 2007 Dec 7.
6
Fragmentation of trifluoromethylated alkenes and acetylenes by N,N-binucleophiles. Synthesis of imidazolines or imidazolidines (oxazolidines) controlled by substituent.N,N-双亲核试剂对三氟甲基化烯烃和炔烃的断裂反应。取代基控制的咪唑啉或咪唑烷（恶唑烷）的合成。
J Org Chem. 2010 Aug 20;75(16):5679-88. doi: 10.1021/jo101107t.
7
Total syntheses of codonopsinine and 4-epi-codonopsinine via gold-mediated tandem-catalyzed pyrrole synthesis.通过金介导的串联催化吡咯合成实现党参碱和4-表党参碱的全合成。
J Antibiot (Tokyo). 2016 Apr;69(4):253-8. doi: 10.1038/ja.2016.13. Epub 2016 Feb 17.
8
Total synthesis and determination of the absolute configuration of guadinomines B and C2.胍地诺明B和C2的全合成及绝对构型的确定
Chemistry. 2008;14(27):8220-38. doi: 10.1002/chem.200801024.
9
Stereoselective Synthesis of Cyclic Guanidines by Directed Diamination of Unactivated Alkenes.非活化烯烃的定向二胺化反应构建环状胍
Org Lett. 2016 Nov 4;18(21):5532-5535. doi: 10.1021/acs.orglett.6b02778. Epub 2016 Oct 25.
10
Rhodium(II)-catalysed tandem aziridination and ring-opening: stereoselective synthesis of functionalised tetrahydrofurans.铑（II）催化的串联氮杂环丙烷化和开环反应：官能化四氢呋喃的立体选择性合成
Chem Commun (Camb). 2014 Oct 7;50(77):11393-6. doi: 10.1039/c4cc05159a.
引用本文的文献
1
Stereoselective Synthesis and Structural Confirmation of the Specialized Pro-Resolving Mediator Resolvin E4.特殊促消退介质解炎素E4的立体选择性合成与结构确证
J Org Chem. 2021 Feb 19;86(4):3535-3545. doi: 10.1021/acs.joc.0c02913. Epub 2021 Feb 3.
2
Unraveling Plant Natural Chemical Diversity for Drug Discovery Purposes.解析植物天然化学多样性以用于药物发现
Front Pharmacol. 2020 Apr 7;11:397. doi: 10.3389/fphar.2020.00397. eCollection 2020.
3
Male-Produced (-)-δ-Heptalactone, Pheromone of Fruit Fly (Diptera: Tephritidae), a Sea Buckthorn Berries Pest.雄性果蝇（双翅目：实蝇科）产生的（-）-δ-庚内酯，沙棘浆果害虫的性信息素
Insects. 2020 Feb 23;11(2):138. doi: 10.3390/insects11020138.
4
Generation and Reactivity of 2-Amido-1,3-diaminoallyl Cations: Cyclic Guanidine Annulations via Net (3 + 2) and (4 + 3) Cycloadditions.2-酰胺基-1,3-二氨基烯丙基阳离子的生成与反应性：通过净（3 + 2）和（4 + 3）环加成的环状胍环化。
Org Lett. 2020 Feb 21;22(4):1407-1413. doi: 10.1021/acs.orglett.0c00019. Epub 2020 Feb 3.
本文引用的文献
1
Short Total Synthesis of [N]-Cylindrospermopsins from NHCl Enables Precise Quantification of Freshwater Cyanobacterial Contamination.[NHCl]介导的[ N]-柱胞藻素的短全合成法可精确量化淡水蓝藻污染。
J Am Chem Soc. 2018 May 9;140(18):6027-6032. doi: 10.1021/jacs.8b03071. Epub 2018 Apr 25.
2
Stereoselective Synthesis of Cyclic Guanidines by Directed Diamination of Unactivated Alkenes.非活化烯烃的定向二胺化反应构建环状胍
Org Lett. 2016 Nov 4;18(21):5532-5535. doi: 10.1021/acs.orglett.6b02778. Epub 2016 Oct 25.
3
Cutting-Edge and Time-Honored Strategies for Stereoselective Construction of C-N Bonds in Total Synthesis.全合成中立体选择性构建C-N键的前沿与传统策略
Chem Rev. 2016 Apr 13;116(7):4441-557. doi: 10.1021/acs.chemrev.5b00712. Epub 2016 Mar 25.
4
The chemistry and biology of guanidine natural products.胍类天然产物的化学和生物学。
Nat Prod Rep. 2016 Mar;33(3):456-90. doi: 10.1039/c5np00108k. Epub 2015 Dec 22.
5
Syntheses of Cyclic Guanidine-Containing Natural Products.含环胍天然产物的合成
Tetrahedron. 2015 Feb 25;71(8):1145-1173. doi: 10.1016/j.tet.2014.11.056.
6
Copper-catalyzed oxidative three-component synthesis of N, N',N″-trisubstituted guanidines.铜催化氧化三组分合成 N,N',N″-三取代胍。
Org Lett. 2013 Dec 20;15(24):6124-7. doi: 10.1021/ol4029622. Epub 2013 Nov 22.
7
Molecular insights into the biosynthesis of guadinomine: a type III secretion system inhibitor.胍丁胺生物合成的分子机制研究：一种 III 型分泌系统抑制剂。
J Am Chem Soc. 2012 Oct 24;134(42):17797-806. doi: 10.1021/ja308622d. Epub 2012 Oct 10.
8
Chlorotrimethylsilane activation of acylcyanamides for the synthesis of mono-N-acylguanidines.三甲基氯硅烷活化酰基氰酰胺合成单 N-酰基胍。
J Org Chem. 2011 Aug 19;76(16):6967-71. doi: 10.1021/jo201264j. Epub 2011 Jul 19.
9
A more comprehensive and highly practical solution to enantioselective aldehyde crotylation.一种更全面、更实用的对映选择性醛烯丙基化方法。
J Am Chem Soc. 2011 May 4;133(17):6517-20. doi: 10.1021/ja200712f. Epub 2011 Apr 12.
10
Total synthesis and determination of the absolute configuration of guadinomines B and C2.胍地诺明B和C2的全合成及绝对构型的确定
Chemistry. 2008;14(27):8220-38. doi: 10.1002/chem.200801024.
Zotero 插件