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Journal articles on the topic 'Indole alkaloid synthesis'

Author: Grafiati

Published: 4 June 2021

Last updated: 15 February 2022

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1

Zhang, Ye, Lei Zhang, and Xiangbing Qi. "Total Synthesis of (–)-Alstofolinine A: Selected Furan Oxidation/ Cyclization Cascade." Synlett 31, no. 01 (November 5, 2019): 7–12. http://dx.doi.org/10.1055/s-0039-1690247.

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Indole-fused tetracyclic ring systems containing nitrogen atoms are common core skeletons of many indole alkaloids such as sarpagine, macroline, and ajmaline. Efficient and stereoselective construction of these ring systems can promote the development of the corresponding alkaloid syntheses. In this article, we briefly summarize our current progress toward the application of the aza-Achmatowicz reaction and indole nucleophilic addition reaction cascade for the first asymmetric total synthesis of the macroline-type indole alkaloid (–)-Alstofolinine A. Our synthetic strategy is based on furan oxidation/rearrangement and proceeds from easily accessible materials such as indole and furan derivatives.

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2

Hájíček, Josef. "A Review on Recent Developments in Syntheses of the post-Secodine Indole Alkaloids. Part II: Modified Alkaloid Types." Collection of Czechoslovak Chemical Communications 72, no. 7 (2007): 821–98. http://dx.doi.org/10.1135/cccc20070821.

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The second part of the planned review on developments in the field of total and formal total synthesis of the post-secodine indole alkaloids concentrates on modified alkaloid types, i.e. those skeletons derived from primary types by formation of additional and/or rupture of existing bonds, while connectivities next to indol(e)ine moiety remain intact. It thus reviews the synthesis of alkaloids of quebrachamine/cleavamine type including VLB-bis-indoles, rhazinilam type, aspidofractinine/kopsane and kopsifoline type, as well as kopsijasminilam alkaloids, lapidilectine B and danuphylline. It covers the literature of from 1991-1992 up to approximately end 2006. A review with 174 references.

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3

Gardette, Daniel, Jean-Claude Gramain, Marie-Eve Lepage, and Yves Troin. "Photocyclization of aryl enaminones. An efficient route to indole alkaloid synthons." Canadian Journal of Chemistry 67, no. 2 (February 1, 1989): 213–19. http://dx.doi.org/10.1139/v89-036.

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The photocyclization of enaminones was extended to aryl enaminones bearing a substituent on the aromatic moiety. This reaction was studied in order to achieve the synthesis of indole alkaloid synthons. Trials of regioselectivity control were made by using groups with enhanced steric hindrance. The reactivity of secondary enaminones was tested, and the ratio of C-alkylation to N-alkylation was shown to be dependent on the nature of the aromatic substituent. During this work, new hexahydrocarbazolones were synthesized, with substituents on the A ring or the modified C ring. Keywords: photocyclization, aryl enaminones, indole alkaloids, hexahydrocarbazolones-4, cyclopenta[b]indoles.

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4

Hájíček, Josef. "Recent developments in syntheses of the post-secodine indole alkaloids. Part III: Rearranged alkaloid types." Collection of Czechoslovak Chemical Communications 76, no. 12 (2011): 2023–83. http://dx.doi.org/10.1135/cccc2011099.

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The third part of a planned review on developments in the field of total and formal total synthesis of the post-secodine indole alkaloids focuses on types of rearranged alkaloids, i.e. on the skeletons with altered connectivities next to the indol(e)ine moiety, especially with a new bond to N-1. It reviews the synthesis of melodane, goniomitine, chippiine/dippinine, lirofoline and tronocarpine alkaloids, as well as alkaloids of secoschizozygane/vallesamidine, schizozygane and isoschizozygane type. It covers the literature from approximately 1991 up to May 2011. A review with 115 references.

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5

Okabe, Kazuaki, Hideaki Muratake, and Mitsutaka Natsume. "Total synthesis of indole alkaloid pendolmycin." Tetrahedron 46, no. 15 (January 1990): 5113–20. http://dx.doi.org/10.1016/s0040-4020(01)87818-2.

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6

Ortuno, J. C., and Y. Langlois. "Stereoselective synthesis of indole alkaloid cuanzine." Tetrahedron Letters 32, no. 35 (January 1991): 4491–94. http://dx.doi.org/10.1016/0040-4039(91)80020-7.

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7

Hájíček, Josef. "A Review on Recent Developments in Syntheses of the Post-Secodine Indole Alkaloids. Part I: The Primary Alkaloid Types." Collection of Czechoslovak Chemical Communications 69, no. 9 (2004): 1681–767. http://dx.doi.org/10.1135/cccc20041681.

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This first part of a planned review on developments in the field of total and formal total synthesis of the post-secodine indole alkaloids concentrates on primary alkaloid types. It reviews the synthesis of secodine, aspidospermane, pseudoaspidospermane and ibogane alkaloids; andranginine is also included. It covers the literature from 1992-1993 up to approximately May 2004. A review with 179 references.

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8

Lounasmaa, Mauri, David Din Belle, and Arto Tolvanen. "Total synthesis of the indole alkaloid (±)-tacamonine." Tetrahedron Letters 36, no. 39 (September 1995): 7141–44. http://dx.doi.org/10.1016/0040-4039(95)01419-i.

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9

Magnus, Philip, Ian R. Matthews, James Schultz, Rudolf Waditschatka, and John C. Huffman. "Synthesis of the hexacyclic indole alkaloid (.+-.)-kopsijasmine." Journal of Organic Chemistry 53, no. 24 (November 1988): 5772–76. http://dx.doi.org/10.1021/jo00259a031.

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10

Zhu, Chenlong, Zhaobo Liu, Guanyu Chen, Kai Zhang, and Hanfeng Ding. "Total Synthesis of Indole Alkaloid Alsmaphorazine D." Angewandte Chemie 127, no. 3 (November 21, 2014): 893–96. http://dx.doi.org/10.1002/ange.201409827.

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11

Zhu, Chenlong, Zhaobo Liu, Guanyu Chen, Kai Zhang, and Hanfeng Ding. "Total Synthesis of Indole Alkaloid Alsmaphorazine D." Angewandte Chemie International Edition 54, no. 3 (November 21, 2014): 879–82. http://dx.doi.org/10.1002/anie.201409827.

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12

Tian, Jingjing, Qiuchen Du, Rui Guo, Yun Li, Bin Cheng, and Hongbin Zhai. "Total Synthesis of Indole Alkaloid (±)-Subincanadine E." Organic Letters 16, no. 12 (May 28, 2014): 3173–75. http://dx.doi.org/10.1021/ol501308p.

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13

Wang, Xiaobei. "Indole Alkaloid Synthesis via Radical Cascade Reactions." Chem 2, no. 6 (June 2017): 749–50. http://dx.doi.org/10.1016/j.chempr.2017.05.012.

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14

Lounasmaa, Mauri, David Din Belle, and Arto Tolvanen. "Total synthesis of the indole alkaloid (±)-tacamine." Tetrahedron Letters 35, no. 33 (August 1994): 6151–54. http://dx.doi.org/10.1016/0040-4039(94)88102-2.

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15

Liu, Xiaoxiang, and James M. Cook. "General Approach for the Synthesis of Sarpagine/Macroline Indole Alkaloids. Enantiospecific Total Synthesis of the Indole Alkaloid Trinervine." Organic Letters 3, no. 25 (December 2001): 4023–26. http://dx.doi.org/10.1021/ol0101990.

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16

Fochi, Mariafrancesca, Luca Bernardi, and Lorenzo Caruana. "Enantioselective Approaches to 3,4-Annulated Indoles Using Organocatalytic Domino Reactions." Synlett 28, no. 13 (April 19, 2017): 1530–43. http://dx.doi.org/10.1055/s-0036-1589494.

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Organocatalytic domino reactions of 4-substituted indoles are summarized in this account. Two reactions have been developed, one with enals, activated by secondary amine catalysts via iminium ions, and one with nitroethene, using a phosphoric acid catalyst. Both reactions required solving the challenge posed by the very low nucleophilicity of the indole substrates, which bear an electron-withdrawing Michael acceptor at C4. DFT calculations were used to shed light on the unique reaction pathway followed by the phosphoric acid catalyzed transformation, wherein a bicoordinated nitronic acid intermediate was found to evolve preferentially through an intramolecular nitro-Michael reaction, instead of the common tautomerization pathway. These reactions provide new and efficient entries to 3,4-ring-fused indoles in diastereo- and enantioenriched form. In more detail, the structures obtained feature a 1,3,4,5-tetrahydrobenzo[cd]indole core, which is present in the structural framework of ergot alkaloids. Indeed, the preparation of an intermediate previously used in ergot alkaloid (6,7-secoagroclavine) synthesis was possible from one of the catalytic adducts.1 Introduction2 Reactions of 4-Substituted Indoles with α,β-Unsaturated Aldehydes Catalyzed by Secondary Amines3 Reactions of 4-Substituted Indoles with Nitroethene Catalyzed by Brønsted Acids4 Conclusion

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17

Lunagariya, Jignesh, Poonam Bhadja, Shenghui Zhong, Rohit Vekariya, and Shihai Xu. "Marine Natural Product Bis-indole Alkaloid Caulerpin: Chemistry and Biology." Mini-Reviews in Medicinal Chemistry 19, no. 9 (May 6, 2019): 751–61. http://dx.doi.org/10.2174/1389557517666170927154231.

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Marine bis-indole alkaloids comprise a large and increasingly growing class of secondary metabolites, and continue to deliver a great variety of structural templates for diverse biological targets. The alkaloids derived from marine resources play a crucial role in medicinal chemistry and as chemical agents. In particular, bis-indole alkaloid caulerpin which has been isolated from marine green algae Caulerpa and a red algae Chondria armata at various places around the world, was tested for several therapeutic potentials such as anti-diabetic, antinociceptive, anti-inflammatory, anti-tumor, anti- larvicidal, anti-herpes, anti-tubercular, anti-microbial and immunostimulating activities as well as a means of other chemical agents. Herein, we summarized the discovery and isolation of caulerpin, and its potential medicinal and chemical applications in chronological order with various aspects. Additionally, synthesis of caulerpin and its functional analogues have also been reviewed.

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18

Smits, Gints, and Ronalds Zemribo. "Stereoselective synthesis of an eleganine A core." Organic & Biomolecular Chemistry 18, no. 24 (2020): 4566–68. http://dx.doi.org/10.1039/d0ob00939c.

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19

Tao, Pengyu, Zhuang Chen, and Yanxing Jia. "A concise gram-scale synthesis of ht-13-A via a rhodium-catalyzed intramolecular C–H activation reaction." Chemical Communications 52, no. 75 (2016): 11300–11303. http://dx.doi.org/10.1039/c6cc05930a.

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20

Zheng, Yu, Bei-Bei Yue, Kun Wei, and Yu-Rong Yang. "Short Synthesis of the Monoterpene Indole Alkaloid (±)-Arbornamine." Journal of Organic Chemistry 83, no. 8 (March 28, 2018): 4867–70. http://dx.doi.org/10.1021/acs.joc.8b00529.

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21

Dhanabal, T., R. Sangeetha, and P. S. Mohan. "Fischer indole synthesis of the indoloquinoline alkaloid: cryptosanguinolentine." Tetrahedron Letters 46, no. 26 (June 2005): 4509–10. http://dx.doi.org/10.1016/j.tetlet.2005.04.122.

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22

Bennasar, M. Lluïsa, Ester Zulaica, Juan-Miguel Jiménez, and Joan Bosch. "An alternative synthesis of the indole alkaloid vinoxine." Tetrahedron Letters 31, no. 5 (January 1990): 747–50. http://dx.doi.org/10.1016/s0040-4039(00)94619-7.

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23

Jiang, Biao, Cai-Guang Yang, and Jun Wang. "Enantioselective Synthesis of Marine Indole Alkaloid Hamacanthin B." Journal of Organic Chemistry 67, no. 4 (February 2002): 1396–98. http://dx.doi.org/10.1021/jo0108109.

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24

Bennasar, M. Lluïsa, Ester Zulaica, Daniel Solé, Tomàs Roca, Davinia García-Díaz, and Sandra Alonso. "Total Synthesis of the Bridged Indole Alkaloid Apparicine." Journal of Organic Chemistry 74, no. 21 (November 6, 2009): 8359–68. http://dx.doi.org/10.1021/jo901986v.

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25

Matsuda, Yohei, Mariko Kitajima, and Hiromitsu Takayama. "First Total Synthesis of Trimeric Indole Alkaloid, Psychotrimine." Organic Letters 10, no. 1 (January 2008): 125–28. http://dx.doi.org/10.1021/ol702637r.

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26

Chatterjee, A., A. Sahu, M. Saha, and J. Banerji. "synthesis of sempervirine, a pentacyclic anhydronium indole alkaloid." Monatshefte für Chemie - Chemical Monthly 127, no. 12 (December 1996): 1259–62. http://dx.doi.org/10.1007/bf00807793.

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27

Naik, Nilesh H., Tukaram D. Urmode, Arun K. Sikder, and Radhika S. Kusurkar. "Total Synthesis of Bouchardatine." Australian Journal of Chemistry 66, no. 9 (2013): 1112. http://dx.doi.org/10.1071/ch13331.

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Two new, efficient and simple routes using Heck-type reaction and intramolecular cyclization were developed for the synthesis of the naturally occurring cytotoxic alkaloid 2-(4-oxo-3,4-dihydroquinazolin-2-yl)-1H-indole-3-carbaldehyde (bouchardatine).

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28

Li, Sena, Jing Han, and Ang Li. "Interrupted Fisher Indole Synthesis and Its Applications to Alkaloid Synthesis." Acta Chimica Sinica 71, no. 3 (2013): 295. http://dx.doi.org/10.6023/a13010018.

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29

Liu, Xiaoxiang, and James M. Cook. "ChemInform Abstract: General Approach for the Synthesis of Sarpagine/Macroline Indole Alkaloids. Enantiospecific Total Synthesis of the Indole Alkaloid Trinervine." ChemInform 33, no. 20 (May 21, 2010): no. http://dx.doi.org/10.1002/chin.200220168.

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30

LOUNASMAA, M., D. DIN BELLE, and A. TOLVANEN. "ChemInform Abstract: Synthetic Studies Towards the Indole Alkaloid Tacamine. Part 2. Total Synthesis of the Indole Alkaloid (.+-.)-Tacamine." ChemInform 26, no. 1 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199501233.

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31

Itoh, Tomoki, Yuusuke Chiba, Shunsuke Kawaguchi, Yuki Koitaya, Yuuma Yoneta, Koji Yamada, and Takumi Abe. "Total synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by a double cyclization strategy." RSC Advances 9, no. 18 (2019): 10420–24. http://dx.doi.org/10.1039/c9ra02321f.

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The regioselective synthesis of pyrano[3,2-e]indole alkaloid fontanesine B have been accomplished by C4 Pictet–Spengler cyclization and Bischler–Napieralski-type cyclization of a trichloromethyl carbamate.

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32

Cardwell, Kevin, Brian Hewitt, and Philip Magnus. "Methods for indole alkaloid synthesis. Compatibility of the 16-methoxy substituent with the indole-2,3-quinodimethane strategy to -type indole alkaloids." Tetrahedron Letters 28, no. 29 (January 1987): 3303–6. http://dx.doi.org/10.1016/s0040-4039(00)95497-2.

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33

Alves, José C. F. "Goniomitine: An Overview on the Chemistry of This Indole Alkaloid." ISRN Organic Chemistry 2013 (December 23, 2013): 1–14. http://dx.doi.org/10.1155/2013/292396.

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34

Bremner, John B., Waya Sengpracha, Ian Southwell, Chris Bourke, Brian W. Skelton, and Allan H. White. "A Revised Structure for the Alkaloid, Tribulusterine, from Tribulus terrestris L." Australian Journal of Chemistry 57, no. 3 (2004): 273. http://dx.doi.org/10.1071/ch03230.

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The alkaloid tribulusterine, first obtained from the fruit of Tribulus terrestris L. and considered to be 1-[(3-hydroxymethyl)-2-furyl]-9H-pyrido[3,4-b]indole, has been shown by synthesis and spectroscopic analysis to be the (5-hydroxymethyl)-2-furyl analogue. This is the known β-carboline alkaloid, perlolyrine. The synthesis of the 3-hydroxymethyl compound is discussed and its single crystal X-ray structure reported.

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35

Bergman, Jan, Ann-Louise Johnson, Johnny Sl閣t, and Tomasz Janosik. "Stereoselective Synthesis and Isomerization of the Indole Alkaloid Murrayacarine." HETEROCYCLES 68, no. 10 (2006): 2165. http://dx.doi.org/10.3987/com-06-10828.

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36

Sharpe, Robert J., and Jeffrey S. Johnson. "Asymmetric Total Synthesis of the Indole Diterpene Alkaloid Paspaline." Journal of Organic Chemistry 80, no. 19 (September 23, 2015): 9740–66. http://dx.doi.org/10.1021/acs.joc.5b01844.

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37

Somei, Masanori, and Toshiya Kawasaki. "The First and Simple Synthesis of Indole Alkaloid, Bipolaramide." HETEROCYCLES 42, no. 1 (1996): 281. http://dx.doi.org/10.3987/com-95-s21.

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38

Amat, Mercedes, Begoña Checa, Núria Llor, Elies Molins, and Joan Bosch. "Enantioselective total synthesis of the indole alkaloid 16-episilicine." Chemical Communications, no. 20 (2009): 2935. http://dx.doi.org/10.1039/b904521j.

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39

Yao, Jian-Neng, Xiao Liang, Kun Wei, and Yu-Rong Yang. "Catalytic, Enantioselective Formal Synthesis of Monoterpene Indole Alkaloid (−)-Alstoscholarine." Organic Letters 21, no. 20 (October 9, 2019): 8485–87. http://dx.doi.org/10.1021/acs.orglett.9b03319.

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40

LOUNASMAA, M., D. DIN BELLE, and A. TOLVANEN. "ChemInform Abstract: Total Synthesis of the Indole Alkaloid (.+-.)-Tacamonine." ChemInform 27, no. 2 (August 12, 2010): no. http://dx.doi.org/10.1002/chin.199602277.

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41

Mascal, Mark, Kyle V. Modes, and Asuman Durmus. "Concise Photochemical Synthesis of the Antimalarial Indole Alkaloid Decursivine." Angewandte Chemie 123, no. 19 (April 7, 2011): 4537–38. http://dx.doi.org/10.1002/ange.201006423.

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42

Mascal, Mark, Kyle V. Modes, and Asuman Durmus. "Concise Photochemical Synthesis of the Antimalarial Indole Alkaloid Decursivine." Angewandte Chemie International Edition 50, no. 19 (April 7, 2011): 4445–46. http://dx.doi.org/10.1002/anie.201006423.

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43

Tian, Jingjing, Qiuchen Du, Rui Guo, Yun Li, Bin Cheng, and Hongbin Zhai. "ChemInform Abstract: Total Synthesis of Indole Alkaloid (.+-.)-Subincanadine E." ChemInform 45, no. 51 (December 4, 2014): no. http://dx.doi.org/10.1002/chin.201451205.

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44

Wei, Yi, Duo Zhao, and Dawei Ma. "Total Synthesis of the Indole Alkaloid (±)- and (+)-MethylN-Decarbomethoxychanofruticosinate." Angewandte Chemie International Edition 52, no. 49 (November 20, 2013): 12988–91. http://dx.doi.org/10.1002/anie.201307788.

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45

Teng, Mingxing, Weiwei Zi, and Dawei Ma. "Total Synthesis of the Monoterpenoid Indole Alkaloid (±)-Aspidophylline A." Angewandte Chemie International Edition 53, no. 7 (January 31, 2014): 1814–17. http://dx.doi.org/10.1002/anie.201310928.

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46

Wei, Yi, Duo Zhao, and Dawei Ma. "Total Synthesis of the Indole Alkaloid (±)- and (+)-MethylN-Decarbomethoxychanofruticosinate." Angewandte Chemie 125, no. 49 (November 20, 2013): 13226–29. http://dx.doi.org/10.1002/ange.201307788.

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47

Teng, Mingxing, Weiwei Zi, and Dawei Ma. "Total Synthesis of the Monoterpenoid Indole Alkaloid (±)-Aspidophylline A." Angewandte Chemie 126, no. 7 (January 31, 2014): 1845–48. http://dx.doi.org/10.1002/ange.201310928.

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48

Palmieri, Alessandro, and Marino Petrini. "Tryptophol and derivatives: natural occurrence and applications to the synthesis of bioactive compounds." Natural Product Reports 36, no. 3 (2019): 490–530. http://dx.doi.org/10.1039/c8np00032h.

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This report presents some fundamental aspects related to the natural occurrence and bioactivity of tryptophol as well as the synthesis of tryptophols and their utilization for the preparation of naturally occurring alkaloid metabolites embedding the indole system.

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49

Ramkissoon, Antonio, Mohindra Seepersaud, Anderson Maxwell, Jayaraj Jayaraman, and Adesh Ramsubhag. "Isolation and Antibacterial Activity of Indole Alkaloids from Pseudomonas aeruginosa UWI-1." Molecules 25, no. 16 (August 17, 2020): 3744. http://dx.doi.org/10.3390/molecules25163744.

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In this study, we report the first isolation of three antibiotic indole alkaloid compounds from a Pseudomonad bacterium, Pseudomonas aeruginosa UWI-1. The bacterium was batch fermented in a modified Luria Broth medium and compounds were solvent extracted and isolated by bioassay-guided fractionation. The three compounds were identified as (1) tris(1H-indol-3-yl) methylium, (2) bis(indol-3-yl) phenylmethane, and (3) indolo (2, 1b) quinazoline-6, 12 dione. A combination of 1D and 2D NMR, high-resolution mass spectrometry data and comparison from related data from the literature was used to determine the chemical structures of the compounds. Compounds 1–3 were evaluated in vitro for their antimicrobial activities against a wide range of microorganisms using the broth microdilution technique. Compounds 1 and 2 displayed antibacterial activity against only Gram-positive pathogens, although 1 had significantly lower minimum inhibitory concentration (MIC) values than 2. Compound 3 displayed potent broad-spectrum antimicrobial activity against a range of Gram positive and negative bacteria. Several genes identified from the genome of P. aeruginosa UWI-1 were postulated to contribute to the biosynthesis of these compounds and we attempted to outline a possible route for bacterial synthesis. This study demonstrated the extended metabolic capability of Pseudomonas aeruginosa in synthesizing new chemotypes of bioactive compounds.

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50

Fang, Jiaqi, Tao Huang, Mengyuan Xia, Lulu Deng, Xiaojiang Hao, Yuehu Wang, and Shuzhen Mu. "Design and synthesis of novel monoterpenoid indole alkaloid-like analogues and their antitumour activities in vitro." Organic & Biomolecular Chemistry 16, no. 16 (2018): 3026–37. http://dx.doi.org/10.1039/c8ob00677f.

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