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Paratunamides A−D, Oxindole Alkaloids from Cinnamodendron axillare

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Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan, Institute of Applied Biochemistry, University of Tsukuba, Tsukuba, Ibaraki, 305-8572, Japan, and Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, Tokyo 101-0062, Japan
Cite this: J. Nat. Prod. 2006, 69, 10, 1517–1521
Publication Date (Web):September 30, 2006
https://doi.org/10.1021/np0602968
Copyright © 2006 American Chemical Society and American Society of Pharmacognosy
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Abstract

Abstract Image

Four new oxindole alkaloids, paratunamides A−D (14), containing a secologanin unit, were isolated from the bark of Cinnamodendron axillare, and their structures and relative configurations were elucidated by spectroscopic data. The absolute configuration at C-7 in 14 was assigned as S, S, R, and S, respectively, on the basis of the CD spectra.

 Hokkaido University.

§

 University of Tsukuba.

 Tokyo Medical and Dental University.

*

 Corresponding author. Tel:  +81-11-706-3239. Fax:  +81-11-706-4989. E-mail:  [email protected]

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  2. James R. Donald, Richard J. K. Taylor, and Wade F. Petersen . Low-Temperature, Transition-Metal-Free Cross-Dehydrogenative Coupling Protocol for the Synthesis of 3,3-Disubstituted Oxindoles. The Journal of Organic Chemistry 2017, 82 (20) , 11288-11294. https://doi.org/10.1021/acs.joc.7b02085
  3. Marc Montesinos-Magraner, Carlos Vila, Gonzalo Blay, Isabel Fernández, M. Carmen Muñoz, and José R. Pedro . Hydroxy-Directed Enantioselective Hydroxyalkylation in the Carbocyclic Ring of Indoles. Organic Letters 2017, 19 (7) , 1546-1549. https://doi.org/10.1021/acs.orglett.7b00354
  4. Goutam Brahmachari and Bubun Banerjee . Facile and One-Pot Access of 3,3-Bis(indol-3-yl)indolin-2-ones and 2,2-Bis(indol-3-yl)acenaphthylen-1(2H)-one Derivatives via an Eco-Friendly Pseudo-Multicomponent Reaction at Room Temperature Using Sulfamic Acid as an Organo-Catalyst. ACS Sustainable Chemistry & Engineering 2014, 2 (12) , 2802-2812. https://doi.org/10.1021/sc500575h
  5. Xiangjin Lian, Songsong Guo, Gang Wang, Lili Lin, Xiaohua Liu, and Xiaoming Feng . Asymmetric Synthesis of Spiro[isoxazolin-3,3′-oxindoles] via the Catalytic 1,3-Dipolar Cycloaddition Reaction of Nitrile Oxides. The Journal of Organic Chemistry 2014, 79 (16) , 7703-7710. https://doi.org/10.1021/jo5012625
  6. V. U. Bhaskara Rao, Amol P. Jadhav, Dnyaneshwar Garad, and Ravi P. Singh . Asymmetric Vinylogous Mannich Reaction of Silyloxy Furans with N-tert-Butanesulfinyl Ketimines. Organic Letters 2014, 16 (3) , 648-651. https://doi.org/10.1021/ol4037117
  7. Qiao Ren, Jiayao Huang, Lei Wang, Wenjun Li, Hui Liu, Xuefeng Jiang, and Jian Wang . Highly Efficient Assembly of 3-Hydroxy Oxindole Scaffold via a Catalytic Decarboxylative [1,2]-Addition Strategy. ACS Catalysis 2012, 2 (12) , 2622-2625. https://doi.org/10.1021/cs300628w
  8. Elisa G. Gutierrez, Casey J. Wong, Aziza H. Sahin, and Annaliese K. Franz . Enantioselective and Regioselective Indium(III)-Catalyzed Addition of Pyrroles to Isatins. Organic Letters 2011, 13 (21) , 5754-5757. https://doi.org/10.1021/ol202329s
  9. Anand Singh and Gregory P. Roth . A [3 + 2] Dipolar Cycloaddition Route to 3-Hydroxy-3-alkyl Oxindoles: An Approach to Pyrrolidinoindoline Alkaloids. Organic Letters 2011, 13 (8) , 2118-2121. https://doi.org/10.1021/ol200547m
  10. Thomas Jensen and Robert Madsen. Ruthenium-Catalyzed Alkylation of Oxindole with Alcohols. The Journal of Organic Chemistry 2009, 74 (10) , 3990-3992. https://doi.org/10.1021/jo900341w
  11. Tripetch Kanchanapoom, Poolsak Sahakitpichan, Nitirat Chimnoi, Chaleaw Petchthong, Wassapol Thamniyom, Phonchanok Nangkoed, Somsak Ruchirawat. Monoterpene alkaloid glycosides from the leaves of Nauclea orientalis. Phytochemistry Letters 2021, 41 , 83-87. https://doi.org/10.1016/j.phytol.2020.11.016
  12. Yu Lim Lee, Kyu Ree Lee, Zi Xuan, Sang‐gi Lee. Dual Rh( II )/Pd(0) Relay Catalysis for One‐Pot Synthesis of α‐Quaternary Allylated Indolin‐2‐ones and Benzofuran‐2‐ones. Bulletin of the Korean Chemical Society 2021, 7 https://doi.org/10.1002/bkcs.12211
  13. Amreen K. Bains, Ayanangshu Biswas, Debashis Adhikari. Nickel-catalysed chemoselective C-3 alkylation of indoles with alcohols through a borrowing hydrogen method. Chemical Communications 2020, 56 (98) , 15442-15445. https://doi.org/10.1039/D0CC07169B
  14. V. Sharma, S. Begam, K. Nurjamal, G. Brahmachari, V. K. Gupta. Synthesis, Characterization, and Crystal Structure of [3,3':3',3''-Terindolin]-2'-One Bis(dimethyl Sulfoxide). Crystallography Reports 2020, 65 (7) , 1187-1190. https://doi.org/10.1134/S1063774520070159
  15. Chengyuan Wang, Zhuopeng Li, Jiong Zhang, Xin-Ping Hui. Asymmetric N -alkylation of indoles with isatins catalyzed by N-heterocyclic carbene: efficient synthesis of functionalized cyclic N , O -aminal indole derivatives. Organic Chemistry Frontiers 2020, 7 (13) , 1647-1652. https://doi.org/10.1039/D0QO00237B
  16. Mikas Sadauskas, Roberta Statkevičiūtė, Justas Vaitekūnas, Rolandas Meškys. Bioconversion of Biologically Active Indole Derivatives with Indole-3-Acetic Acid-Degrading Enzymes from Caballeronia glathei DSM50014. Biomolecules 2020, 10 (4) , 663. https://doi.org/10.3390/biom10040663
  17. Alison B. da Silva, Francisco C.L. Pinto, Edilberto R. Silveira, Leticia V. Costa-Lotufo, Wendell S. Costa, Alejandro Pedro Ayala, Kirley M. Canuto, Ayslan B. Barros, Ana Jérsia Araújo, José Delano B. Marinho Filho, Otilia Deusdenia L. Pessoa. 4-Hydroxy-pyran-2-one and 3-hydroxy-N-methyl-2-oxindole derivatives of Salinispora arenicola from Brazilian marine sediments. Fitoterapia 2019, 138 , 104357. https://doi.org/10.1016/j.fitote.2019.104357
  18. Karu Ramesh, Gedu Satyanarayana. Domino [Pd]-Catalysis: Heck followed by decarboxylative Sonogashira couplings under microwave irradiation in aqueous medium. Journal of Organometallic Chemistry 2019, 890 , 58-71. https://doi.org/10.1016/j.jorganchem.2019.03.015
  19. Yun‐Long Wei, Yajun Ren, Damien Mailhol, Michel Rajzmann, Jean Rodriguez, Yoann Coquerel. An Organocatalytic Two‐atom Ring Expansion Approach to Optically Active Glutarimides. Advanced Synthesis & Catalysis 2019, 361 (12) , 2992-3001. https://doi.org/10.1002/adsc.201900159
  20. Mubarak B. Dambatta, Kurt Polidano, Alexander D. Northey, Jonathan M. J. Williams, Louis C. Morrill. Iron‐Catalyzed Borrowing Hydrogen C ‐Alkylation of Oxindoles with Alcohols. ChemSusChem 2019, https://doi.org/10.1002/cssc.201900799
  21. Xiaojian Jiang, Haitao Wang, Haoquan He, Wei Wang, Yuqiang Wang, Zhihai Ke, Ying-Yeung Yeung. Enantioseletive Fluorination of 3-Functionalized Oxindoles Using Electron-rich Amino Urea Catalyst. Advanced Synthesis & Catalysis 2018, 360 (24) , 4710-4714. https://doi.org/10.1002/adsc.201801133
  22. Raj Kumar Tak, Naveen Gupta, Manish Kumar, Rukhsana I. Kureshy, Noor-ul H. Khan, E. Suresh. Regioselective Alcoholysis and Hydrochlorination Reactions of Spiro-Epoxy Oxindoles at the Spiro-Centre: Synthesis of 3,3-Disubstituted Oxindoles and Application for Anticancer Agents. European Journal of Organic Chemistry 2018, 2018 (41) , 5678-5687. https://doi.org/10.1002/ejoc.201801002
  23. Sonal Bhandari, Amol Rajaram Katore, Deepti Madanlal Bajaj, Pankaj Sharma, Venu Talla, Nagula Shankaraiah. H 2 O-Mediated Epoxide Ring-Opening with Concomitant C-S Bond Formation: A One-Pot Method to 3-Hydroxy-oxindolino-dithiocarbamates as Cytotoxic Agents. ChemistrySelect 2018, 3 (24) , 6766-6774. https://doi.org/10.1002/slct.201800983
  24. Deevi Basavaiah, Harathi Lingam, Thelagathoti Hari Babu. Baylis-Hillman acetates in organic synthesis: A simple two-step strategy for oxindole-spiro-α-arylidene-γ-butyrolactone framework. Tetrahedron 2018, 74 (19) , 2306-2313. https://doi.org/10.1016/j.tet.2018.03.035
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  28. Hui-qin Pan, Wen-zhi Yang, Dan Zhao, Cheng Luo, Chang-liang Yao, Xiao-jian Shi, Yi-bei Zhang, Shi-you Li, Ying Bi, Zhen Wang, Shuai Yao, Wan-ying Wu, De-an Guo. New monoterpenoid oxindole alkaloid derivatives from the stems of Uncaria hirsuta Havil. and their cytotoxicity and tandem mass spectrometric fragmentation. Fitoterapia 2017, 116 , 85-92. https://doi.org/10.1016/j.fitote.2016.11.013
  29. Bangzhi Zhang, Yiping Li, Guangjun Bao, Gongming Zhu, Jing Li, Juanli Wang, Bao Zhang, Wangsheng Sun, Liang Hong, Rui Wang. Regio- and stereoselective ring-opening reaction of spiro-epoxyoxindoles with ammonia under catalyst-free conditions. Green Chemistry 2017, 19 (9) , 2107-2110. https://doi.org/10.1039/C7GC00438A
  30. Long Fan, Cheng-Hui Liao, Qiang-Rong Kang, Kai Zheng, Ying-Chun Jiang, Zhen-Dan He. Indole Alkaloids from the Leaves of Nauclea officinalis. Molecules 2016, 21 (8) , 968. https://doi.org/10.3390/molecules21080968
  31. Jia Zhao, Shuicheng Guan, Xiaojian Zhou, Wenyong Han, Baodong Cui, Yongzheng Chen. Bioreduction of the C C double bond with Pseudomonas monteilii ZMU-T17: one approach to 3-monosubstituted oxindoles. Tetrahedron 2016, 72 (22) , 3098-3104. https://doi.org/10.1016/j.tet.2016.04.037
  32. Keshri Nath Tiwari, Darshana Bora, Garima Chauhan, Deepika Yadav, Kavita Sharma, Ashima Thakur, Lachhman Singh, Vishwadeep Tripathi. DABCO-catalyzed synthesis of 3-substituted-3-hydroxyindolin-2-ones in aqueous media. Synthetic Communications 2016, 46 (7) , 620-625. https://doi.org/10.1080/00397911.2016.1160411
  33. Sakshi Sharma, Bubun Banerjee, Goutam Brahmachari, Rajni Kant, Vivek K. Gupta. Synthesis, characterization, and crystal structure of 5,5″-Difluoro-1H,1″H-[3,3′:3′,3″-terindol]-2′(1′H)-one. Crystallography Reports 2016, 61 (2) , 225-229. https://doi.org/10.1134/S1063774516020218
  34. Nagaraju Molleti, Jun Yong Kang. . Organic & Biomolecular Chemistry 2016,,, 8952. https://doi.org/10.1039/C6OB01608A
  35. Goutam Brahmachari. Design for carbon–carbon bond forming reactions under ambient conditions. RSC Advances 2016, 6 (69) , 64676-64725. https://doi.org/10.1039/C6RA14399G
  36. Baoshuang Wang, Jiayi Zhu, Yang Wei, Guotian Luo, Hongen Qu, Liang-Xian Liu. C U 2 O-Catalyzed C( SP 3 )-H/C( SP 3 )-H Cross-Coupling Using TEMPO: Synthesis of 3-(2-Oxoalkyl)-3-hydroxyoxindoles. Synthetic Communications 2015, 45 (24) , 2841-2848. https://doi.org/10.1080/00397911.2015.1111383
  37. Anggi Eka Putra, Yohei Oe, Tetsuo Ohta. Pd/C-Catalyzed Alkylation of Heterocyclic Nucleophiles with Alcohols through the “Borrowing Hydrogen” Process. European Journal of Organic Chemistry 2015, 2015 (35) , 7799-7805. https://doi.org/10.1002/ejoc.201501030
  38. Mukesh Gangar, Naresh Kashyap, Kapil Kumar, Sandeep Goyal, Vipin A. Nair. Imidazolidinone based chiral auxiliary mediated acetate aldol reactions of isatin derivatives and stereoselective synthesis of 3-substituted-3-hydroxy-2-oxindoles. Tetrahedron Letters 2015, 56 (51) , 7074-7081. https://doi.org/10.1016/j.tetlet.2015.11.007
  39. Muhammad Taha, Nor Hadiani Ismail, Ajmal Khan, Syed Adnan Ali Shah, Ammarah Anwar, Sobia Ahsan Halim, M. Qaiser Fatmi, Syahrul Imran, Fazal Rahim, Khalid Mohammed Khan. Synthesis of novel derivatives of oxindole, their urease inhibition and molecular docking studies. Bioorganic & Medicinal Chemistry Letters 2015, 25 (16) , 3285-3289. https://doi.org/10.1016/j.bmcl.2015.05.069
  40. Adrien Quintard, Diana Cheshmedzhieva, Maria del Mar Sanchez Duque, Anouk Gaudel-Siri, Jean-Valère Naubron, Yves Génisson, Jean-Christophe Plaquevent, Xavier Bugaut, Jean Rodriguez, Thierry Constantieux. Origin of the Enantioselectivity in Organocatalytic Michael Additions of β-Ketoamides to α,β-Unsaturated Carbonyls: A Combined Experimental, Spectroscopic and Theoretical Study. Chemistry - A European Journal 2015, 21 (2) , 778-790. https://doi.org/10.1002/chem.201404481
  41. Huang Huang, Yong Xu, Fei Mao, Jin Zhu, Hualiang Jiang, Jian Li. A highly efficient approach to unnatural amino-acids containing 3-hydroxyoxindole skeleton via a one-pot, three-component procedure. Tetrahedron Letters 2015, 56 (4) , 586-589. https://doi.org/10.1016/j.tetlet.2014.12.011
  42. Kishna Ram Senwar, Pankaj Sharma, Shalini Nekkanti, Manda Sathish, Ahmed Kamal, B. Sridhar, Nagula Shankaraiah. A one-pot ‘click’ reaction from spiro-epoxides catalyzed by Cu( i )-pyrrolidinyl-oxazole-carboxamide. New Journal of Chemistry 2015, 39 (5) , 3973-3981. https://doi.org/10.1039/C4NJ02131B
  43. V. U. Bhaskara Rao, Krishna Kumar, Ravi P. Singh. . Organic & Biomolecular Chemistry 2015,,, 9755. https://doi.org/10.1039/C5OB01560J
  44. Ruihong Wang, Weiliang Bao. Copper promoted radical addition/cyclization of azobisisobutyronitrile with arylacrylamides: a convenient process to synthesize 3-(2′-cyano alkyl) oxindoles. RSC Advances 2015, 5 (71) , 57469-57471. https://doi.org/10.1039/C5RA07739G
  45. Pramod B. Thakur, K. Sirisha, A.V.S. Sarma, Harshadas M. Meshram. Microwave assisted rapid, catalyst-free, and efficient synthesis of a new class of diversely functionalized 3-hydroxy-2-oxindole scaffolds under aqueous reaction media. Tetrahedron Letters 2014, 55 (15) , 2459-2462. https://doi.org/10.1016/j.tetlet.2014.03.008
  46. Sébastien Goudedranche, Xavier Bugaut, Thierry Constantieux, Damien Bonne, Jean Rodriguez. α,β-Unsaturated Acyl Cyanides as New Bis-Electrophiles for Enantioselective Organocatalyzed Formal [3+3]Spiroannulation. Chemistry - A European Journal 2014, 20 (2) , 410-415. https://doi.org/10.1002/chem.201303613
  47. Tao Deng, Hongjun Wang, Chun Cai. Fluorous chiral bisoxazolines: application in copper-catalyzed asymmetric α-hydrophosphonylation. Organic & Biomolecular Chemistry 2014, 12 (31) , 5843. https://doi.org/10.1039/C4OB01144A
  48. Selvam Kaladevi, Jeyaraman Sridhar, Brahmanandan Abhilashamole, Shanmugam Muthusubramanian, Nattamai Bhuvanesh. Synthesis of substituted 1,3-diaryl-6,7-dihydro-1H-indol-4(5H)-ones from 1-aryl-2-arylaminoethanones. RSC Advances 2014, 4 (65) , 34382. https://doi.org/10.1039/C4RA03975K
  49. Pramod B. Thakur, Harshadas M. Meshram. “On water” catalyst-free, column chromatography-free and atom economical protocol for highly diastereoselective synthesis of novel class of 3-substituted, 3-hydroxy-2-oxindole scaffolds at room temperature. RSC Advances 2014, 4 (11) , 5343. https://doi.org/10.1039/c3ra46271d
  50. Pramod B. Thakur, Harshadas M. Meshram. “On water” highly atom economical and rapid synthesis of a novel class of 3-hydroxy-2-oxindole scaffolds under a catalyst-free and column chromatography-free protocol at room temperature. RSC Advances 2014, 4 (12) , 6019. https://doi.org/10.1039/c3ra46613b
  51. Tingting Yan, Xiaoyan Wang, Hongbao Sun, Jie Liu, Yongmei Xie. Facile Creation of 3-Substituted-3-Hydroxy-2-Oxindoles by Arginine-Catalyzed Aldol Reactions of α,β-Unsaturated Ketones with Isatins. Molecules 2013, 18 (12) , 14505-14518. https://doi.org/10.3390/molecules181214505
  52. Pramod Bhagwan Thakur, Katukuri Sirisha, Akella Venkata Subrahmanya Sarma, Jagadeesh Babu Nanubolu, Harshadas Mitaram Meshram. Highly regioselective and metal-free γ-addition of β-keto esters to isatins, catalyzed by DABCO: direct access to novel class of diversely functionalized 3-hydroxy-2-oxindole scaffolds. Tetrahedron 2013, 69 (31) , 6415-6423. https://doi.org/10.1016/j.tet.2013.05.101
  53. Pramod B. Thakur, Jagadeesh Babu Nanubolu, H.M. Meshram. WITHDRAWN: DABCO promoted unprecedented γ-addition of β-keto sulfones to isatins: regioselective synthesis of a novel class of diversely functionalized 3-hydroxy-2-oxindole scaffolds. Tetrahedron Letters 2013, https://doi.org/10.1016/j.tetlet.2013.06.054
  54. Changcheng Jing, Taoda Shi, Dong Xing, Xin Guo, Wen-Hao Hu. CuSO4-catalyzed three-component reaction of α-diazo ester, water and isatin: an efficient approach to oxindole derivatives. Green Chemistry 2013, 15 (3) , 620. https://doi.org/10.1039/c2gc36708d
  55. Zhiqiang Duan, Jianlin Han, Ping Qian, Zirui Zhang, Yi Wang, Yi Pan. Enantioselective synthesis of 3-hydroxy oxindoles by ytterbium-catalysed decarboxylative addition of β-ketoacids to isatins. Organic & Biomolecular Chemistry 2013, 11 (38) , 6456. https://doi.org/10.1039/c3ob41460d
  56. Anand Singh, Gregory P. Roth. Efficient assembly of 3-substituted oxindole-based isoxazolines leading to the synthesis of (±)-flustraminol-B and related natural product building blocks. Tetrahedron Letters 2012, 53 (36) , 4889-4891. https://doi.org/10.1016/j.tetlet.2012.07.005
  57. Abbas Rahmati, Kobra Vakili. Synthesis of 3,3-Disubstituted Oxindoles via a Three-Component Condensation Reaction in H2O. Helvetica Chimica Acta 2012, 95 (7) , 1126-1135. https://doi.org/10.1002/hlca.201100506
  58. Qing-Hai Deng, Hubert Wadepohl, Lutz H. Gade. The Synthesis of a New Class of Chiral Pincer Ligands and Their Applications in Enantioselective Catalytic Fluorinations and the Nozaki-Hiyama-Kishi Reaction. Chemistry - A European Journal 2011, 17 (52) , 14922-14928. https://doi.org/10.1002/chem.201102375
  59. Lu Liu, Shilei Zhang, Fei Xue, Guangshun Lou, Haoyi Zhang, Shichao Ma, Wenhu Duan, Wei Wang. Catalytic Enantioselective Henry Reactions of Isatins: Application in the Concise Synthesis of ( S )‐(−)‐Spirobrassinin. Chemistry – A European Journal 2011, 17 (28) , 7791-7795. https://doi.org/10.1002/chem.201101025
  60. Mangilal Chouhan, Ratnesh Sharma, Vipin A. Nair. Cp2ZrCl2-induced Reformatsky and Barbier reactions on isatins: an efficient synthesis of 3-substituted-3-hydroxyindolin-2-ones. Applied Organometallic Chemistry 2011, 25 (6) , 470-475. https://doi.org/10.1002/aoc.1789
  61. Guohua Liu, Tianzeng Huang, Yuli Zhang, Xiaohui Liang, Yunsheng Li, Hexing Li. C-3 alkylation of oxindole with alcohols catalyzed by an indene-functionalized mesoporous iridium catalyst. Catalysis Communications 2011, 12 (7) , 655-659. https://doi.org/10.1016/j.catcom.2010.12.021
  62. Mangilal Chouhan, Kishna Ram Senwar, Ratnesh Sharma, Vikas Grover, Vipin A. Nair. Regiospecific epoxide opening: a facile approach for the synthesis of 3-hydroxy-3-aminomethylindolin-2-one derivatives. Green Chemistry 2011, 13 (9) , 2553. https://doi.org/10.1039/c1gc15416h
  63. Bin Yin, Laihao Wang, Shinsuke Inagi, Toshio Fuchigami. Electrosynthesis of fluorinated indole derivatives. Tetrahedron 2010, 66 (34) , 6820-6825. https://doi.org/10.1016/j.tet.2010.06.063
  64. Jing Deng, Shilei Zhang, Peng Ding, Hualiang Jiang, Wei Wang, Jian Li. Facile Creation of 3-Indolyl-3-hydroxy-2-oxindoles by an Organocatalytic Enantioselective Friedel-Crafts Reaction of Indoles with Isatins. Advanced Synthesis & Catalysis 2010, 352 (5) , 833-838. https://doi.org/10.1002/adsc.200900851
  65. Fei Xue, Shilei Zhang, Lu Liu, Wenhu Duan, Wei Wang. Organocatalytic Enantioselective Cross-Aldol Reactions of Aldehydes with Isatins: Formation of Two Contiguous Quaternary Centered 3-Substituted 3-Hydroxyindol-2-ones. Chemistry - An Asian Journal 2009, 4 (11) , 1664-1667. https://doi.org/10.1002/asia.200900243
  66. Minoru Ishikura, Koji Yamada. Simple indole alkaloids and those with a nonrearranged monoterpenoid unit. Natural Product Reports 2009, 26 (6) , 803. https://doi.org/10.1039/b820693g
  67. Tomoya Fujiwara, Bin Yin, Meixiang Jin, Kenneth L. Kirk, Yoshio Takeuchi. Synthetic studies of 3-(3-fluorooxindol-3-yl)-l-alanine. Journal of Fluorine Chemistry 2008, 129 (9) , 829-835. https://doi.org/10.1016/j.jfluchem.2008.06.026
  68. Erin T. Pelkey, Jonathon S. Russel. Chapter 5.2 Five-membered ring systems: pyrroles and benzo analogs. 2008,,, 135-175. https://doi.org/10.1016/S0959-6380(08)80008-6
  69. . A critical review of the 2006 literature preceded by two chapters on current heterocyclic topics. 2008,,https://doi.org/

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