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Journal articles on the topic 'Pyrrolizidines'

Author: Grafiati
Published: 4 June 2021
Last updated: 26 July 2025

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1

Jurczak, Janusz, Marcin Lindner, and Antoni Krasiński. "Facile, Stereocontrolled Synthetic Route towards Bis-functionalised Pyrrolizidines." Synthesis 50, no. 21 (2018): 4295–300. http://dx.doi.org/10.1055/s-0037-1609582.

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A simple and convenient method for the synthesis of bis-functionalised pyrrolizidines starting from readily available N-Cbz-l-prolinal is described. This aldehyde was converted within two concise steps to the corresponding aminoepoxides, which were separately subjected to regioselective cyclisation induced by a reductive cleavage of the Cbz protecting group. The versatile and concise strategy holds great potential for practical application in the straightforward preparation of pyrrolizidine-based drugs and natural products.
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2

Reddy, Marri Sameer, Nandigama Satish Kumar, and L. Raju Chowhan. "Heterogeneous graphene oxide as recyclable catalyst for azomethine ylide mediated 1,3 dipolar cycloaddition reaction in aqueous medium." RSC Advances 8, no. 62 (2018): 35587–93. http://dx.doi.org/10.1039/c8ra06714g.

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Graphene oxide (GO) catalyzed regio and diastereoselective synthesis of spiro-indenoquinoxaline pyrrolizidines and spiro-oxindoles pyrrolizidines is described with good substrate scope and yield using azomethine ylide under aq. EtOH condition at RT.
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3

Nájera, Carmen, and José Miguel Sansano. "Synthesis of pyrrolizidines and indolizidines by multicomponent 1,3-dipolar cycloaddition of azomethine ylides." Pure and Applied Chemistry 91, no. 4 (2019): 575–96. http://dx.doi.org/10.1515/pac-2018-0710.

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Abstract Different multicomponent 1,3-dipolar cycloadditions (1,3-DC) of cyclic α-amino acid derivatives with aldehydes and dipolarophiles have been described as efficient and simple methodologies for the synthesis of the pyrrolidine unit of pyrrolizidines and indolizidines. When free cyclic α-amino acids are used, a thermal promoted decarboxylative process generates in situ the corresponding non-stabilized azomethine ylides, which afforded the corresponding pyrrolizidines and indolizidines with a hydrogen in the bicyclic units. This methodology has been employed to the synthesis of complex sy
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4

Egorov, Victor A., Lidiya S. Khasanova, Fanuza A. Gimalova, Alexander N. Lobov, and Mansur S. Miftakhov. "Straightforward synthesis of pyrrolizidines." Mendeleev Communications 27, no. 2 (2017): 163–65. http://dx.doi.org/10.1016/j.mencom.2017.03.019.

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5

Massicot, Fabien, Gatien Messire, Alexis Vallée, Jean-Luc Vasse, Sandrine Py, and Jean-Bernard Behr. "Regiospecific formation of sugar-derived ketonitrone towards unconventional C-branched pyrrolizidines and indolizidines." Organic & Biomolecular Chemistry 17, no. 29 (2019): 7066–77. http://dx.doi.org/10.1039/c9ob01419e.

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6

Coelho, Fernando, Kristerson de Luna Freire, and Cláudio Tormena. "Heck Reaction on Morita-Baylis-Hillman Adducts: Diastereoselective Synthesis of Pyrrolizidinones and Pyrrolizidines." Synlett 2011, no. 14 (2011): 2059–63. http://dx.doi.org/10.1055/s-0030-1261161.

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7

Klipkov, Anton, Igor Gerus, and Alexander Sorochinsky. "Synthesis of fluorinated pyrrolizidine, indolizidine and quinolizidine derivatives." Ukr. Bioorg. Acta 2022, Vol. 17, N1 17, no. 1 (2022): 22–39. http://dx.doi.org/10.15407/bioorganica2022.01.022.

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This review provides literature data dealing with the synthesis of fluorinated pyrrolizidines, indolizidines, and quinolizidines. Synthesis of trifluoromethylated derivatives requires to use of commercially available building blocks bearing pre-installed trifluoromethyl group or synthetic trifluoromethylated templates incorporating a chiral auxiliary as starting materials. On the other hand, nucleophilic or radical difluoromethylation followed by cyclization reactions using different types of stable and readily available difluoromethylating agents was established as an efficient approach for t
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8

Samala, Srinivas, Do Hyun Ryu, Choong Eui Song, and Eun Jeong Yoo. "Multicomponent dipolar cycloadditions: efficient synthesis of polycyclic fused pyrrolizidinesviaazomethine ylides." Organic & Biomolecular Chemistry 17, no. 7 (2019): 1773–77. http://dx.doi.org/10.1039/c8ob02463d.

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9

Biswas, Rayhan G., and Vinod K. Singh. "Direct enantioselective synthesis of pyrrolizidines." Tetrahedron Letters 69 (April 2021): 152954. http://dx.doi.org/10.1016/j.tetlet.2021.152954.

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10

Shahrestani, Naeimeh, Hormoz Khosravi, Khosrow Jadidi, Behrouz Notash, and Soheila Naderi. "Organocatalytic synthesis of enantiopure spiro acenaphthyl-pyrrolizidine/pyrrolidines: justifying the regioselectivity based on a distortion/interaction model." Organic & Biomolecular Chemistry 17, no. 29 (2019): 7013–24. http://dx.doi.org/10.1039/c9ob01197h.

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An efficient organocatalytic synthesis of chiral spiroacenaphthyl-pyrrolidines/pyrrolizidines with high regio- and diastereoselectivity (up to 99%) with exact specification of the absolute configuration is described for the first time.
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11

Gallos, John K., Vassiliki C. Sarli, Theocharis V. Koftis, and Evdoxia Coutouli-Argyropoulou. "A new entry to hydroxylated pyrrolizidines." Tetrahedron Letters 41, no. 24 (2000): 4819–22. http://dx.doi.org/10.1016/s0040-4039(00)00732-2.

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12

Tamayo, Juan A., Francisco Franco, Daniele Lo Re, and Fernando Sánchez-Cantalejo. "Synthesis of Pentahydroxylated Pyrrolizidines and Indolizidines†." Journal of Organic Chemistry 74, no. 15 (2009): 5679–82. http://dx.doi.org/10.1021/jo900801c.

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13

de Figueiredo, Renata Marcia, Roland Fröhlich, and Mathias Christmann. "Efficient Synthesis and Resolution of Pyrrolizidines." Angewandte Chemie 119, no. 16 (2007): 2941–44. http://dx.doi.org/10.1002/ange.200605035.

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14

de Figueiredo, Renata Marcia, Roland Fröhlich, and Mathias Christmann. "Efficient Synthesis and Resolution of Pyrrolizidines." Angewandte Chemie International Edition 46, no. 16 (2007): 2883–86. http://dx.doi.org/10.1002/anie.200605035.

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15

Sirisha, N., and R. Raghunathan. "Regioselective Synthesis of Dispiro Pyrrolizidines as Potent Antimicrobial Agents for Human Pathogens." ISRN Medicinal Chemistry 2013 (September 10, 2013): 1–8. http://dx.doi.org/10.1155/2013/492604.

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Synthesis of a series of novel dispiro pyrrolizidines has been accomplished by 1,3-dipolar cycloaddition reaction of azomethine ylide generated from secondary amino acids and diketones with bischalcones. These compounds were evaluated for their antibacterial activity. Most of the synthetic compounds exhibited good antibacterial activity against microorganisms.
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16

Ikeda, Masazumi, Masazumi Ikeda, Tatsunori Sato, and Hiroyuki Ishibashi. "Recent Advances in the Synthesis of Pyrrolizidines." HETEROCYCLES 27, no. 6 (1988): 1465. http://dx.doi.org/10.3987/rev-87-381.

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17

Nagao, Yoshimitsu, Wei-Min Dai, and Eiichi Fujita. "Recent Progress in Asysmmetric Synthesis of Pyrrolizidines." HETEROCYCLES 30, no. 2 (1990): 1231. http://dx.doi.org/10.3987/rev-89-sr8.

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18

Yu-Mei, Zhang, Liu Peng, Zhang Hong-Li, Feng Guo-Liang, and Geng Li-Jun. "Microwave-assisted synthesis of novel ferrocenyl pyrrolizidines." Journal of Chemical Research 36, no. 9 (2012): 536–38. http://dx.doi.org/10.3184/174751912x13418562888522.

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19

Lim, Andrew D., Julian A. Codelli, and Sarah E. Reisman. "Catalytic asymmetric synthesis of highly substituted pyrrolizidines." Chem. Sci. 4, no. 2 (2013): 650–54. http://dx.doi.org/10.1039/c2sc21617e.

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20

Vassilikogiannakis, G., D. Kalaitzakis, M. Triantafyllakis, M. Sofiadis, and D. Noutsias. "Pyrrolizidines and Indolizidines by Photooxidation of Furylalkylamines." Synfacts 12, no. 09 (2016): 995. http://dx.doi.org/10.1055/s-0036-1589168.

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21

Nallamala, Sirisha, Srikumar Mannem, and Raghunathan Raghavachary. "Highly Efficient Construction of Sugar-Fused Spirochromanono Pyrrolidines/Pyrrolizidines/Thiolizidines via 1,3-Dipolar Cycloaddition of Azomethine Ylides." SynOpen 01, no. 01 (2017): 0063–67. http://dx.doi.org/10.1055/s-0036-1588520.

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A variety of sugar-fused chromanono pyrrolidines/pyrrolizidines/thiolizidines have been synthesized by intermolecular 1,3-dipolar cycloaddition reaction of azomethine ylides (generated from glucose aldehyde and different secondary amino acids) with various 3-arylidene chroman-4-ones as dipolarophiles. The solvent effect on the 1,3-dipolar cycloaddition reaction is also studied.
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22

Luna-Freire, Kristerson R., João Paulo S. Scaramal, Jackson A. L. C. Resende, et al. "An asymmetric substrate-controlled Morita–Baylis–Hillman reaction as approach for the synthesis of pyrrolizidinones and pyrrolizidines." Tetrahedron 70, no. 20 (2014): 3319–26. http://dx.doi.org/10.1016/j.tet.2013.10.050.

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23

Izquierdo, Isidoro, Marı́a T. Plaza, and Juan A. Tamayo. "Polyhydroxylated pyrrolizidines. Part 5: Stereoselective synthesis of 1,2-dihydroxypyrrolizidines as a model for the preparation of densely polyhydroxylated pyrrolizidines." Tetrahedron: Asymmetry 15, no. 22 (2004): 3635–42. http://dx.doi.org/10.1016/j.tetasy.2004.10.003.

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24

Zhang, Xiaofeng, Xiaoming Ma, Weiqi Qiu, JohnMark Awad, and Wei Zhang. "Double [3 + 2] cycloadditions for diastereoselective synthesis of spirooxindole pyrrolizidines." Green Processing and Synthesis 11, no. 1 (2022): 1128–35. http://dx.doi.org/10.1515/gps-2022-0088.

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Abstract One-pot two sequential [3 + 2] cycloadditions of azomethine ylides with different dipolarophiles for diastereoselective synthesis of spirooxindole pyrrolizidines are introduced. This one-pot synthesis involving five components generates a highly condensed ring system bearing seven stereocenters diastereoselectively. The new method has high pot, atom, and step economy. Only two equivalents of water are released as a side product.
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25

Gademann, Karl, and Isabel Kerschgens. "Direct Preparation of Pyrrolizidines Using Imines and Isonitriles." Synthesis 47, no. 20 (2015): 3153–60. http://dx.doi.org/10.1055/s-0034-1380433.

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26

Vavrecka, Majmir, Agnes Janowitz, and Manfred Hesse. "Transformation of 4-nitroalkane-1,7-diones into pyrrolizidines." Tetrahedron Letters 32, no. 40 (1991): 5543–46. http://dx.doi.org/10.1016/0040-4039(91)80079-l.

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27

Hanusch, Jan M., Isabel P. Kerschgens, Florian Huber, Markus Neuburger, and Karl Gademann. "Pyrrolizidines for direct air capture and CO2 conversion." Chemical Communications 55, no. 7 (2019): 949–52. http://dx.doi.org/10.1039/c8cc08574a.

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28

Tiwari, Keshri Nath, Taur Prakash Pandurang, Suyash Pant, and P. Sreelekha. "Efficient synthesis of spirooxindole-pyrrolizidines and dispirooxindole-piperazines." Synthetic Communications 48, no. 7 (2018): 802–8. http://dx.doi.org/10.1080/00397911.2018.1425726.

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29

Kang, Sung Ho, Geun Tae Kim, and Yong Sang Yoo. "An enantiocontrolled synthesis of pyrrolizidines, (−)-platynecine and (−)-hadinecine." Tetrahedron Letters 38, no. 4 (1997): 603–6. http://dx.doi.org/10.1016/s0040-4039(96)02371-4.

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30

Blankenship, Jimmy D., Justin B. Houseknecht, Sitaram Pal, Lowell P. Bush, Robert B. Grossman, and Christopher L. Schardl. "Biosynthetic Precursors of Fungal Pyrrolizidines, the Loline Alkaloids." ChemBioChem 7, no. 3 (2006): 404. http://dx.doi.org/10.1002/cbic.200690008.

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31

Gallos, John K., Vassiliki C. Sarli, Theocharis V. Koftis, and Evdoxia Coutouli-Argyropoulou. "ChemInform Abstract: A New Entry to Hydroxylated Pyrrolizidines." ChemInform 31, no. 36 (2010): no. http://dx.doi.org/10.1002/chin.200036230.

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32

Blankenship, Jimmy D., Justin B. Houseknecht, Sitaram Pal, Lowell P. Bush, Robert B. Grossman, and Christopher L. Schardl. "Biosynthetic Precursors of Fungal Pyrrolizidines, the Loline Alkaloids." ChemBioChem 6, no. 6 (2005): 1016–22. http://dx.doi.org/10.1002/cbic.200400327.

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33

Lewis, Wilfred J. M., David M. Shaw, and Jeremy Robertson. "Synthesis of legonmycins A and B, C(7a)-hydroxylated bacterial pyrrolizidines." Beilstein Journal of Organic Chemistry 17 (February 2, 2021): 334–42. http://dx.doi.org/10.3762/bjoc.17.31.

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A one-flask, two-step procedure from 3-amino-2-methyl-5,6,7,7a-tetrahydro-1H-pyrrolizin-1-one affords the Streptomyces secondary metabolites legonmycins A and B – three operations overall from methyl N-Boc-prolinate. The key step proceeds in each case via N,O-diacylation, then selective oxidative hydrolysis of the intermediate bicyclic pyrrole and establishes a precedent for the synthesis of related C(7a)-hydroxylated pyrrolizidines.
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34

Luna-Freire, Kristerson R., Joao Paulo S. Scaramal, Jackson A. L. C. Resende, et al. "ChemInform Abstract: An Asymmetric Substrate-Controlled Morita-Baylis-Hillman Reaction as Approach for the Synthesis of Pyrrolizidinones and Pyrrolizidines." ChemInform 45, no. 40 (2014): no. http://dx.doi.org/10.1002/chin.201440134.

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35

Despinoy, Xavier L. M., and Hamish McNab. "Hydrogenation of pyrrolizin-3-ones; new routes to pyrrolizidines." Organic & Biomolecular Chemistry 7, no. 21 (2009): 4502. http://dx.doi.org/10.1039/b910199c.

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36

Fischer, Robert, Daniela Beňadiková, Michal Medvecký, et al. "New Synthetic Approach to C5-Hydroxymethyl-Substituted Polyhydroxylated Pyrrolizidines." Synlett 25, no. 11 (2014): 1616–20. http://dx.doi.org/10.1055/s-0033-1339123.

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37

KNIGHT, D. W., A. C. SHARE, and P. T. GALLAGHER. "ChemInform Abstract: Syntheses of the Pyrrolizidines (-)-Trachelanthamidine and (-)- Isoretronecanol." ChemInform 22, no. 29 (2010): no. http://dx.doi.org/10.1002/chin.199129274.

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38

KADYROV, A. A., L. L. GERVITS, L. F. KOMAROVA, and K. N. MAKAROV. "ChemInform Abstract: Synthesis of Polyfluoroalkyl-Substituted Pyrrolines and Pyrrolizidines." ChemInform 22, no. 13 (2010): no. http://dx.doi.org/10.1002/chin.199113171.

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39

Zhang, Yu-Mei, Peng Liu, Hong-Li Zhang, Guo-Liang Feng, and Li-Jun Geng. "ChemInform Abstract: Microwave-Assisted Synthesis of Novel Ferrocenyl Pyrrolizidines." ChemInform 44, no. 6 (2013): no. http://dx.doi.org/10.1002/chin.201306147.

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40

Lim, Andrew D., Julian A. Codelli, and Sarah E. Reisman. "ChemInform Abstract: Catalytic Asymmetric Synthesis of Highly Substituted Pyrrolizidines." ChemInform 44, no. 27 (2013): no. http://dx.doi.org/10.1002/chin.201327106.

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41

Kornev, Anton A., Stanislav V. Shmakov, Alexandra M. Gryschenko, et al. "Study of Cytotoxicity of 3-Azabicyclo[3.1.0]hexanes and Cyclopropa[a]pyrrolizidines Spiro-Fused to Acenaphthylene-1(2H)-one and Aceanthrylene-1(2H)-one Fragments Against Tumor Cell Lines." International Journal of Molecular Sciences 26, no. 8 (2025): 3474. https://doi.org/10.3390/ijms26083474.

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A series of 3-azabicyclo[3.1.0]hexanes and cyclopropa[a]pyrrolizidines spiro-fused to acenaphthylene-1(2H)-one and aceanthrylene-1(2H)-one frameworks have been studied for their in vitro antiproliferative activity against human erythroleukemia (K562), cervical carcinoma (HeLa), melanoma (Sk-mel-2), osteosarcoma (U2OS), as well as murine melanoma (B16) cell lines. Using confocal microscopy, it was found that cultivation with the tested spiro-fused compounds led to the disappearance of stress fibers (granular actin was distributed diffusely in the cytoplasm in up to 56% of treated cells) and dec
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42

Wu, Mingshu, Jie Jiang, Zhongxiang Zhu, and Dulin Kong. "Catalyst-Free Intramolecular 1,3-Dipolar Cycloaddition of Ethyl (2-Formylphenyl) Vinylphosphonates: A Highly Stereoselective Access to Phosphadihydrocoumarin-Fused Pyrrolizidines/Pyrrolidines." Synthesis 49, no. 16 (2017): 3731–39. http://dx.doi.org/10.1055/s-0036-1588818.

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Pyrrolizidine and coumarins both have biological activities, and their molecular skeletons are commonly found in several biomolecules and drug molecules. We have developed a catalyst-free, intramolecular 1,3-dipolar cycloaddition to synthesize phosphadihydrocoumarin-fused pyrrolizidine/pyrrolidine scaffolds with high stereoselectivity.
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43

Kumar, Nakul, Gajendra Kumar Inwati, Emad M. Ahmed, et al. "Modified 7-Chloro-11H-indeno[1,2-b]quinoxaline Heterocyclic System for Biological Activities." Catalysts 12, no. 2 (2022): 213. http://dx.doi.org/10.3390/catal12020213.

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Recent advances in functionalized organic Spiro heterocyclic compounds composed of nitrogen bonded five- and six-membered rings have been made, establishing them as a synthetic target in organic-based biomedical applications. In this work, we report a synthesis of spirocyclic compounds under a one-pot reaction using 1,3-dipolar cycloaddition in a regio and diastereoselective manner. The higher atomic economy with higher yield (95%) and regio and stereoselectivity were achieved by a multi-component reaction of L-proline (1), Indenoquinoxaline (2), and the dipolarophile of malononitrile (3) solv
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44

Garraffo, H. M., J. Caceres, J. W. Daly, T. F. Spande, N. R. Andriamaharavo, and M. Andriantsiferana. "Alkaloids in Madagascan Frogs (Mantella): Pumiliotoxins, Indolizidines, Quinolizidines, and Pyrrolizidines." Journal of Natural Products 56, no. 7 (1993): 1016–38. http://dx.doi.org/10.1021/np50097a005.

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45

Bowman, W. Russell, David N. Clark, and Robert J. Marmon. "Synthesis of pyrrolizidines using aminyl radicals generated from sulfenamide precursors." Tetrahedron 50, no. 4 (1994): 1295–310. http://dx.doi.org/10.1016/s0040-4020(01)80838-3.

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46

de Vicente, Javier, Ramón Gómez Arrayás, and Juan C. Carretero. "An efficient and stereoselective synthesis of enantiopure 1,2,7-trihydroxylated pyrrolizidines." Tetrahedron Letters 40, no. 33 (1999): 6083–86. http://dx.doi.org/10.1016/s0040-4039(99)01265-4.

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47

De Smaele, Dirk, Piet Bogaert, and Norbert De Kimpe. "Synthesis of pyrrolizidines by cascade reactions of N-alkenylaziridinylmethyl radicals." Tetrahedron Letters 39, no. 52 (1998): 9797–800. http://dx.doi.org/10.1016/s0040-4039(98)02176-5.

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48

Zhang, Wei, Kasumi Sato, Atsushi Kato, et al. "Synthesis of Fully Substituted Polyhydroxylated Pyrrolizidines via Cope–House Cyclization." Organic Letters 13, no. 16 (2011): 4414–17. http://dx.doi.org/10.1021/ol201749c.

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49

Kathiravan, Subban, Raghavachary Raghunathan, Gopalakrishnan Suresh, and Ganesan Vijaiyan Siva. "Synthesis and antimicrobial activities of novel ferrocenyl dispiropyrrolidines and pyrrolizidines." Medicinal Chemistry Research 21, no. 10 (2011): 3170–76. http://dx.doi.org/10.1007/s00044-011-9852-5.

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50

Lieou Kui, Evelyn, Alice Kanazawa, Jean-Bernard Behr, and Sandrine Py. "Ring-Junction-Substituted Polyhydroxylated Pyrrolizidines and Indolizidines from Ketonitrone Cycloadditions." European Journal of Organic Chemistry 2018, no. 19 (2018): 2178–92. http://dx.doi.org/10.1002/ejoc.201800212.

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