含环胍天然产物的合成
Syntheses of Cyclic Guanidine-Containing Natural Products.
作者信息
Ma Yuyong, De Saptarshi, Chen Chuo
机构信息
Division of Chemistry, Department of Biochemistry, U T Southwestern Medical Center, 5323 Harry Hines Boulevard, Dallas, TX 75390-9038, USA.
出版信息
Tetrahedron. 2015 Feb 25;71(8):1145-1173. doi: 10.1016/j.tet.2014.11.056.
Abstract
Naturally occurring guanidine derivatives frequently display medicinally useful properties. Among them, the higher order pyrrole-imidazole alkaloids, the dragmacidins, the crambescidins/batzelladines, and the saxitoxins/tetradotoxins have stimulated the development of many new synthetic methods over the past decades. We provide here an overview of the syntheses of these cyclic guanidine-containing natural products.
摘要
天然存在的胍衍生物常常具有药用特性。其中，高阶吡咯 - 咪唑生物碱、龙涎香毒素、海兔毒素/石房蛤毒素在过去几十年间推动了许多新合成方法的发展。在此，我们概述这些含环状胍的天然产物的合成方法。
相似文献
1
Syntheses of Cyclic Guanidine-Containing Natural Products.
Tetrahedron. 2015 Feb 25;71(8):1145-1173. doi: 10.1016/j.tet.2014.11.056.
2
Polycyclic Guanidine Alkaloids from Poecilosclerida Marine Sponges.
Mar Drugs. 2016 Apr 9;14(4):77. doi: 10.3390/md14040077.
3
[Total synthesis of marine cyclic guanidine compounds and development of novel guanidine type asymmetric organocatalysts].
Yakugaku Zasshi. 2003 Jun;123(6):387-98. doi: 10.1248/yakushi.123.387.
4
Fused Tricyclic Guanidine Alkaloids: Insights into Their Structure, Synthesis and Bioactivity.
Mar Drugs. 2022 Sep 17;20(9):579. doi: 10.3390/md20090579.
5
Inhibition of HIV-1 envelope-mediated fusion by synthetic batzelladine analogues.
J Nat Prod. 2004 Aug;67(8):1319-24. doi: 10.1021/np049958o.
6
A Survey on the Synthesis of Variolins, Meridianins, and Meriolins-Naturally Occurring Marine (aza)Indole Alkaloids and Their Semisynthetic Derivatives.
Molecules. 2023 Jan 18;28(3):947. doi: 10.3390/molecules28030947.
7
Synthetic approaches to tetracyclic pyrrole imidazole marine alkaloids.
Nat Prod Commun. 2013 Jul;8(7):961-4.
8
Synthesis of marine guanidine alkaloids and their application as chemical/biological tools.
Chem Rec. 2003;3(4):201-11. doi: 10.1002/tcr.10064.
9
Chemistry and Biology of the Pyrrole-Imidazole Alkaloids.
Alkaloids Chem Biol. 2017;77:117-219. doi: 10.1016/bs.alkal.2016.12.001. Epub 2017 Jan 20.
10
Pyrrole carboxamide introduction in the total synthesis of pyrrole-imidazole alkaloids.
Org Biomol Chem. 2021 Mar 28;19(12):2603-2621. doi: 10.1039/d0ob02052d. Epub 2021 Mar 8.
引用本文的文献
1
Efficient construction of the hexacyclic ring core of palau'amine: the p concept for proceeding with unfavorable equilibrium reactions.
Chem Sci. 2021 Aug 11;12(36):12201-12210. doi: 10.1039/d1sc03260g. eCollection 2021 Sep 22.
2
Generation and Reactivity of 2-Amido-1,3-diaminoallyl Cations: Cyclic Guanidine Annulations via Net (3 + 2) and (4 + 3) Cycloadditions.
Org Lett. 2020 Feb 21;22(4):1407-1413. doi: 10.1021/acs.orglett.0c00019. Epub 2020 Feb 3.
3
Copper-Hydride-Catalyzed Enantioselective Processes with Allenyl Boronates. Mechanistic Nuances, Scope, and Utility in Target-Oriented Synthesis.
J Am Chem Soc. 2019 Jul 31;141(30):12087-12099. doi: 10.1021/jacs.9b05465. Epub 2019 Jul 17.
4
Synthesis of N-H Bearing Imidazolidinones and Dihydroimidazolones Using Aza-Heck Cyclizations.
Angew Chem Int Ed Engl. 2018 Sep 10;57(37):12081-12085. doi: 10.1002/anie.201806295. Epub 2018 Aug 19.
5
A Nitrone Dipolar Cycloaddition Strategy toward an Enantioselective Synthesis of Massadine.
Org Lett. 2018 Jul 6;20(13):3883-3887. doi: 10.1021/acs.orglett.8b01464. Epub 2018 Jun 13.
6
Total Synthesis of (+)-Guadinomic Acid via Hydroxyl-Directed Guanidylation.
J Org Chem. 2018 Aug 17;83(16):9492-9496. doi: 10.1021/acs.joc.8b01214. Epub 2018 Jun 22.
7
Thio acid-mediated conversion of azides to amides - exploratory studies en route to oroidin alkaloids.
Tetrahedron Lett. 2017 Oct 11;58(41):3913-3918. doi: 10.1016/j.tetlet.2017.08.050. Epub 2017 Aug 24.
8
Rapid access to the core skeleton of the [3 + 2]-type dimeric pyrrole-imidazole alkaloids by triplet ketone-mediated C-H functionalization.
Tetrahedron. 2018 Feb 22;74(8):769-772. doi: 10.1016/j.tet.2017.12.027. Epub 2017 Dec 15.
9
Natural products as inspiration for the development of new synthetic methods.
J Chin Chem Soc. 2018 Jan;65(1):43-59. doi: 10.1002/jccs.201700134. Epub 2017 Aug 9.
10
Batzella, Crambe and Monanchora: Highly Prolific Marine Sponge Genera Yielding Compounds with Potential Applications for Cancer and Other Therapeutic Areas.
Nutrients. 2018 Jan 2;10(1):33. doi: 10.3390/nu10010033.
本文引用的文献
1
An approach for the synthesis of nakamuric acid.
Tetrahedron. 2015 Jun 3;71(22):3690-3693. doi: 10.1016/j.tet.2014.10.027.
2
Asymmetric syntheses of sceptrin and massadine and evidence for biosynthetic enantiodivergence.
Science. 2014 Oct 10;346(6206):219-24. doi: 10.1126/science.1255677.
3
Synthesis of 5- and 8-deoxytetrodotoxin.
Chem Asian J. 2014 Jul;9(7):1922-32. doi: 10.1002/asia.201402202. Epub 2014 May 26.
4
Dimeric pyrrole-imidazole alkaloids: synthetic approaches and biosynthetic hypotheses.
Chem Commun (Camb). 2014 Aug 14;50(63):8628-39. doi: 10.1039/c4cc02290d. Epub 2014 May 15.
5
Saxitoxin.
Angew Chem Int Ed Engl. 2014 Jun 2;53(23):5760-84. doi: 10.1002/anie.201308235. Epub 2014 Apr 25.
6
A dual-catalysis approach to enantioselective [2 + 2] photocycloadditions using visible light.
Science. 2014 Apr 25;344(6182):392-6. doi: 10.1126/science.1251511.
7
Synthesis and identification of proposed biosynthetic intermediates of saxitoxin in the cyanobacterium Anabaena circinalis (TA04) and the dinoflagellate Alexandrium tamarense (Axat-2).
Org Biomol Chem. 2014 May 21;12(19):3016-20. doi: 10.1039/c4ob00071d.
8
Visualizing dermal permeation of sodium channel modulators by mass spectrometric imaging.
J Am Chem Soc. 2014 Apr 30;136(17):6401-5. doi: 10.1021/ja501635u. Epub 2014 Apr 17.
9
Isolation of 6-deoxytetrodotoxin from the pufferfish, Takifugu pardalis, and a comparison of the effects of the C-6 and C-11 hydroxy groups of tetrodotoxin on its activity.
J Nat Prod. 2014 Apr 25;77(4):1000-4. doi: 10.1021/np401097n. Epub 2014 Mar 21.
10
Total synthesis of chiriquitoxin, an analogue of tetrodotoxin isolated from the skin of a dart frog.
Chemistry. 2014 Jan 27;20(5):1247-51. doi: 10.1002/chem.201304110.
Zotero 插件