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Relevant bibliographies by topics / Indolizidine

Academic literature on the topic 'Indolizidine'

Author: Grafiati

Published: 4 June 2021

Last updated: 11 March 2023

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Journal articles on the topic "Indolizidine"

1

Mohajer, Fatemeh, Ghodsi Mohammadi Ziarani, and Razieh Moradi. "The Study of Several Synthesis Methods of Indolizidine (±)-209I and (±)-209B as Natural Alkaloids." Current Organic Chemistry 24, no. 5 (May 17, 2020): 516–35. http://dx.doi.org/10.2174/1385272824666200226113022.

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Natural products have received much attention due to their importance and application. Indolizidine, categorized as an alkaloid, has several biological activities. The synthesis of natural compounds such as indolizidines has attracted much attention from many chemists’ and researchers’ perspectives. There are many areas to be explored in this subject; that is why synthesizing indolizidine 209I and (±)-indolizidine 209B as natural compounds have received much consideration. This review discloses the procedures and methodology to provide (±)-indolizidine 209I and 209B due to the importance of indolizidines.

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Ziarani, Ghodsi Mohammadi, Fatemeh Mohajer, and Zohreh kheilkordi. "Recent Progress Towards Synthesis of the Indolizidine Alkaloid 195B." Current Organic Synthesis 17, no. 2 (May 8, 2020): 82–90. http://dx.doi.org/10.2174/1570179417666200124104010.

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Background: Natural products have been received attention due to their importance in human life as those are biologically active. In this review, there are some reports through different methods related to the synthesis of the indolizidine 195B which was extracted from poisonous frog; however, due to respect nature, the synthesis of natural compounds such as indolizidine has been attracted much attention among scientists and researchers. Objective: This review discloses the procedures and methods to provide indolizidine 195B from 1989 to 2018 due to their importance as a natural product. Conclusion: There are several methods to give rise to the indolizidine 195B as a natural product that is highly active from the biological perspective in pharmaceutical chemistry. In summary, many protocols for the preparations of indolizidine 195B from various substrates, several reagents, and conditions have been reported from different aromatic and aliphatic.

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Riley, Darren L., Joseph P. Michael, and Charles B. de Koning. "New syntheses of (±)-tashiromine and (±)-epitashiromine via enaminone intermediates." Beilstein Journal of Organic Chemistry 12 (December 2, 2016): 2609–13. http://dx.doi.org/10.3762/bjoc.12.256.

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The syntheses of the naturally occurring indolizidine alkaloid (±)-tashiromine and its unnatural epimer (±)-epitashiromine are demonstrated through the use of enaminone chemistry. The impact of various electron-withdrawing substituents at the C-8 position of the indolizidine core on the preparation of the bicyclic system is described.

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Zhou, De-Jun, Zhen-Hui Wang, Yan-Ru Zhang, and Zheng-Guo Cui. "Flexible Syntheses of 5,8-Disubstituted Indolizidine Poisonous-Frog Alkaloids via a Michael-Type Conjugate Addition." Journal of Chemical Research 41, no. 2 (February 2017): 98–105. http://dx.doi.org/10.3184/174751917x14858862342223.

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The efficient and flexible syntheses of 5,8-disubstituted indolizidine poisonous-frog alkaloids is described using a highly stereoselective Michael-type conjugate addition reaction as the key step. In this work, syntheses of the 5,8-disubstituted indolizidine poisonous-frog alkaloids (–)-231C, (–)-221I and the proposed structure for (–)-193E are reported.

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Chou, Shang-Shing P., Shan-Lun Chiang, Guan-Lin Huang, Bi-Shan Chiang, and Ya-Chien Yu. "New synthesis and reactions of indolizidine 167E and indolizidine derivatives." Tetrahedron 69, no. 1 (January 2013): 274–83. http://dx.doi.org/10.1016/j.tet.2012.10.026.

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Smith, Adrian L., Simon F. Williams, Andrew B. Holmes, Leslie R. Hughes, Colin Swithenbank, and Zev Lidert. "Stereoselective synthesis of (.+-.)-indolizidines 167B, 205A, and 207A. Enantioselective synthesis of (-)-indolizidine 209B." Journal of the American Chemical Society 110, no. 26 (December 1988): 8696–98. http://dx.doi.org/10.1021/ja00234a021.

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Holmes, Andrew B., Adrian L. Smith, Simon F. Williams, Leslie R. Hughes, Zev Lidert, and Colin Swithenbank. "Stereoselective synthesis of (.+-.)-indolizidines 167B, 205A, and 207A. Enantioselective synthesis of (-)-indolizidine 209B." Journal of Organic Chemistry 56, no. 4 (February 1991): 1393–405. http://dx.doi.org/10.1021/jo00004a012.

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Chang, Meng-Yang, Tsun-Cheng Wu, and Ya-Jung Ko. "Synthesis of Indolizidine 167B." HETEROCYCLES 71, no. 4 (2007): 933. http://dx.doi.org/10.3987/com-07-10997.

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Michael, Joseph P. "Indolizidine and quinolizidine alkaloids." Natural Product Reports 24, no. 1 (2007): 191. http://dx.doi.org/10.1039/b509525p.

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Michael, Joseph P. "Indolizidine and quinolizidine alkaloids." Natural Product Reports 20, no. 5 (2003): 458. http://dx.doi.org/10.1039/b208137g.

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Dissertations / Theses on the topic "Indolizidine"

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Nelson, A. "Synthesis of bioactive indolizidine alkaloids." Thesis, Queen's University Belfast, 2005. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.421009.

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Padmanabhan, Padma. "Biosynthetic studies on the indolizidine alkaloid cyclizidine." Thesis, University of Cambridge, 1989. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.304387.

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Mitchell, Douglas. "Synthetic studies towards pyrrolizidine and indolizidine alkaloids." Thesis, Sheffield Hallam University, 1992. http://shura.shu.ac.uk/20067/.

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This project was concerned with the synthesis of the pyrrolizidine alkaloids supinidine, trachelanthamidine and isoretronecanol and also synthetic studies towards the indolizidine alkaloid 251D. In all cases, the synthesis began from a cheap, readily-available, simple amino acid, in this case glutamic acid, and proceeded to a suitable monocyclic intermediate which could then undergo an intramolecular Horner-Wittig cyclisation reaction to form the required bicyclic core structure. Subsequent modification reactions then led in the pyrrolizidine series to penultimate precursors of the target alkaloids supinidine, trachelanthamidine and isoretronecanol, and in the indolizidine series to a bicyclic intermediate in the synthesis towards the toxin 251D. The intramolecular Horner-Wittig cyclisation reaction was found to proceed with retention of chirality, thus leading to the enantiospecific synthesis of the pyrrolizidine alkaloids. The use of alternative monocyclic intermediates in the intramolecular Horner-Wittig cyclisation reaction, thus leading to other pyrrolizidine alkaloids is also discussed. One of the major problems encountered in this project was the solubility of the unprotected monocyclic amide intermediates, and this was overcome by the use of N-benzyl and N- carbobenzyloxy protecting groups; in the indolizidine synthesis where the unprotected monocyclic amides were necessary, the reaction work-up for these intermediates usually required continuous solvent extraction. Another major problem was the instability of the bicyclic amide intermediates and some of the monocyclic intermediates,As well as covering a comprehensive background of each class of alkaloid, this report also contains an in-depth discussion of the key intramolecular Horner-Wittig cyclisation reaction and suggestions for its use in the possible synthesis of other classes of alkaloids.

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St-Denis, Yves. "Studies toward the synthesis of hydroxylated indolizidine alkaloids." Thesis, McGill University, 1991. http://digitool.Library.McGill.CA:80/R/?func=dbin-jump-full&object_id=70343.

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The formation of the indolizidine ring system was studied. First, the intramolecular electrophilic cyclisation of substituted allylsilanes, vinylsilanes and enol ethers was attempted. Reactions with the allylsilane moiety indeed gave the desired ring system, whereas the vinylsilanes failed to give any cyclisation product. In order to easily introduce oxygen functionalities in the rings, enol ether cyclisations were also attempted but did not produce the expected bicyclic systems.
Secondly, the intramolecular nucleophilic cyclisation of free amines bearing suitable leaving groups was attempted, providing an easy method for the formation of the indolizidine system, with an interesting entry into the synthesis of biologically active polyhydroxylated alkaloids Swainsonine and Castanospermine. The synthesis of these two natural compounds, as well as some of their analogues, using the successful nucleophilic methodology was attempted.
Finally, the regioselective and stereoselective introduction of hydroxyl groups into the pyrrolidine ring system was studied in order to prepare mono- and di-hydroxylated pyrrolidines for the synthesis of the aforementioned natural products.

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Kefalas, Panagiotis. "Synthèse d'une indolizidine hydroxylée, analogue de la castanospermine." Paris 11, 1988. http://www.theses.fr/1988PA112340.

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Les alcaloïdes indolizidiniques polyhydroxylés comme la swainsonine et la castanospermine ont une activité remarquable vis-à-vis des glycosidases. Nous nous étions fixés comme but, la synthèse de la castanospermine et de ses épimères. Cet alcaloïde a une activité contre le virus du SIDA in vitro et également contre le virus de la grippe. Ces propriétés biologiques permettraient d'envisager une utilisation comme insecticide. Vu la ressemblance de cet alcaloïde et les sucres, il paraît évident d'utiliser des carbohydrates comme produits du départ. Le D-glucose présente une configuration convenable pour les centres C-6, C-7 et C-8 de l'alcaloïde. Dans une première approche de synthèse, nous avons étudié la formation du noyau à cinq chaînons du système indolizidinique en appliquant la chimie des α-aminonitriles sur l'aldéhyde O-1,2-isopropylidène l-α-D-xylo-pentodialdo-furanose-1,4 –issu du D-glucose - de deux façons: soit par formation de l'a-aminonitrile, N-benzylé suivie de l'introduction des carbones C-2 et C-3 par réaction de Grignard sur le nitrile et cyclisation, soit par préparation de l’a-aminonitrile portant les carbones C-2 et C-3 substitués sur la fonction amine et cyclisation. Les difficultés rencontrées au cours de cette voie nous ont contraints à l'abandonner. Dans une deuxième approche, nous avons étudié la formation du noyau indolizidinique polyhydroxylé à partir des dérivés du D-glucose, du D-xylose et du D-arabinose. On introduit les carbones C-1, C-2 et C-3 et l'oxygène en C-1 sous forme d'éther d'énol par réaction de Wittig. Ensuite, on forme une oxazine-1,2-dihydro-3, 6-2H éthoxy-4 par réaction d'hétéro-Diels-Alder avec un diénophile portant la fonction nitroso. Le dérivé du glucose ne répond pas aux conditions requises pour la suite de la synthèse à cause de la sensibilité du noyau furannique au milieu basique de la réaction de Wittig. Les dérivés du D-xylose et du D·arabinose ne portant pas le noyau furannique permettent la poursuite de cette voie. La cyclisation de l'azote de l’oxazine sur le tosylate en position terminale de la chaine d'arabinose fournit un produit bicyclique portant un hydroxyle libre en β de l'azote. En série xylose une réaction concurrentielle de l'hydroxyle secondaire en a du tosylate fournit aussi l'époxyde; cette différence de comportement est due à des effets stériques. La réduction de la double liaison et de la liaison N-O de l’oxazine en série arabinose donnent un δ-aminoalcool. Nous avons tenté trois méthodes de cyclisation déshydratante de cet aminoalcool en utilisant : i) le système PPh₃; NEt₃; CCI4 ii) le complexe de rhodium RhH (PPh₃)₄ iii) le réactif combiné, diéthylazodicarboxylate-triphénylphosphine (réaction de Mitsunobu). Seule la réaction de Mitsunobu a pu fournir le squelette du produit final en série arabinose, la méthode n'ayant pu aboutir pour des raisons stériques quand elle était appliquée au dérivé bicyclique du xylose. On obtient un seul isomère, la(1R,6R,7R,8R,8aS)-éthoxy-1,hydroxy6;O-7,8 isopropylidène, octahydroindolizidine. La réaction de Mitsunobu s'avère stéréosélective puisque l'hydroxyle libre secondaire du noyau à six n'intervient pas à la réaction
Several attempts for the synthesis of the indolizidinic alkaloid (1S,6S,7R,8R,8aR)-1,6,7,8 tetrahydroxy-octahydroindolizine (castanospermine), a glucosidase inhibitor and of its epimers are described. The general synthetic approach was undertaken starting from sugars that have an established configuration on the carbon atoms corresponding to the C-6, C-7 and C-8 centres of the indolizidinic ring. Ln a first synthetic route we have studied the formation of the alkaloid five-member ring, through the application of α-aminonitrile chemistry on the aldehyde 1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose prepared from D-(+)-Glucose; either by formation of the N-benzyl,α-aminonitrile, followed by the introduction of C-2 and C-3 and cyclization, or by the synthesis of the α-aminonitrile carrying C-2 and C-3 substituted on the amine function and ring closure. The difficulties met during this route obliged us to abandon. In a second approach we have studied the formation of the polyhydroxylated indolizidinic ring starting from D-Glucose, D-Xylose and D-Arabinose derivatives; we introduce C-1, C-2 and C-3 and the oxygen on C-1 in the form of an enol ether, by Wittig reaction. Then we form a 1,2-oxazine-3,6- dihydro-2H; 4 ethoxy by Diels-Alder reaction with a dienophile carrying the nitroso function. The glucose derivative does not meet the requirements for the continuation of the synthesis, due to the sensitivity of the furan ring in the basic medium of the Wittig reaction. Cyclization of the oxazine on the tosylated sugar frame supplies a bicyclic product. Reduction of the double bond and the N-O bond of the arabinose series derivative give a δ-aminoalcohol which leads to the (1S,6S,7R,8R,8aS),1-ethoxy,6-hydroxy;7,8-O- isopropylidene octahydroindolizine(ie. A close analog of castanospermine) by dehydrative cyclization. (Mitsunobu reaction). The same reaction sequence could not be used on the bicyclic xylose derivative; the Mitsunobu reaction being inappropriate for steric reasons

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Agarwal, Sameer. "Transition Metal-Mediated Syntheses of Yohimbane and Indolizidine Alkaloids." Doctoral thesis, Saechsische Landesbibliothek- Staats- und Universitaetsbibliothek Dresden, 2005. http://nbn-resolving.de/urn:nbn:de:swb:14-1119360417222-39155.

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Polycyclic nitrogen containing heterocycles form the basic skeleton of numerous alkaloids and physiologically active drugs. Alloyohimbane was obtained from 3,4-dihydro-â-carboline using an iron-mediated [2+2+1] cycloaddition as the key-step. The bis-TMS-diyne was conveniently obtained by the C-alkylation of 3,4-dihydro-â-carboline followed by N-alkylation. Demetalation of the iron-complex followed by hydrogenation, E-ring expansion, and reduction provided alloyohimbane, a structurally and biologically interesting substance, via a linear eight-step sequence in 7% overall yield based on 3,4-dihydro-â-carboline. Another sequence provided (±)-alloyohimbane and (±)-3-epi-alloyohimbane in nine steps. The pyrrole unit occurs in a variety of naturally occurring compounds, pharmaceutical products and polymers. A novel two-step procedure for the synthesis of pyrroles by addition of a propargyl Grignard reagent to a Schiff base and subsequent silver(I)-promoted oxidative cyclization of the resulting homopropargylamine has been developed. The generality of this reaction was proven by the synthesis of a broad variety of substituted pyrroles using silver(I)-promoted cyclization. A three-step synthesis of (±)-harmicine, a natural product isolated from the Malaysian plant Kopsia griffithii having strong anti-leishmania activity, from 3,4-dihydro-â-carboline is achieved by addition of 3-trimethylsilylpropargyl Grignard reagent, Ag(I)-promoted oxidative cyclization to a pyrrole, and chemoselective hydrogenation of pyrrole ring. Total synthesis of anti-tumor active crispine A and biologically active 1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline have been achieved in three steps using silver(I)-promoted oxidative cyclization as key step.

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Kondakal, Vishnu. "The attempted synthesis of indolizidine and pyrrolizidine natural products." Thesis, University of Huddersfield, 2013. http://eprints.hud.ac.uk/id/eprint/19281/.

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Aza-sugars are naturally occurring polyhydroxylated alkaloids in which the ring oxygen is replaced by nitrogen. They are reported to have a wide range of biological properties, most importantly as glycosidase inhibitors; these glycosidases play a key role in various diseases like HIV, cancer and lysosomal storage disorders. This thesis will describe an approach to the synthesis of analogues and precursors of azasugar natural products in the indolizidine (for example castanospermine) and pyrrolizidine (for example hyacinthacine) using cyclopropenones and cyclic imines as key intermediates. This thesis contains work that is an extension of the work pioneered by Eicher and Heimgartner and followed by our group for the reaction of cyclic imines with diphenylcyclopropenone. The methodology was extended towards the synthesis of more complex bicyclic heterocycles like indolizidine and pyrrolizidine aza-sugars and is summarised by the following Scheme. In this thesis, cyclopropenones other than diphenylcyclopropenone were used. This work also extended the range of cyclic imines that can be reacted by using for the first time, the parent aldimines, polyhydroxylated cyclic aldimines synthesised from sugars and other substituted cyclic imines. The reactions gave bicyclic products but always with an extra oxygen at the bridge head postion (X= OH) via aerial oxidation of the initial product (X= H).

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Szeto, Peter. "Recent development in indolizidine alkaloids : a synthesis of (-)-slaframine." Thesis, University of Bristol, 1995. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.294850.

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Kefalas, Panagiotis. "Synthèse asymétrique d'une indolizidine hydroxylée, analogue de la castanospermine." Grenoble 2 : ANRT, 1988. http://catalogue.bnf.fr/ark:/12148/cb37614731r.

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Farrant, Elizabeth. "A novel approach to the synthesis of polyhydroxylated indolizidine alkaloids." Thesis, University of Reading, 1997. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.360718.

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Books on the topic "Indolizidine"

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Jaecques, Ryan Patrick. Studies toward the synthesis of indolizidine alkaloids and analogues using ring-closing metathesis. Ottawa: National Library of Canada, 2003.

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Book chapters on the topic "Indolizidine"

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Seigler, David S. "Pyrrolizidine, Quinolizidine, and Indolizidine Alkaloids." In Plant Secondary Metabolism, 546–67. Boston, MA: Springer US, 1998. http://dx.doi.org/10.1007/978-1-4615-4913-0_30.

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Bronner, Sarah M., G. Yoon J. Im, and Neil K. Garg. "Indoles and Indolizidines." In Heterocycles in Natural Product Synthesis, 221–65. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2011. http://dx.doi.org/10.1002/9783527634880.ch7.

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Herczegh, Pál, Imre Kovács, and Ferenc Sztaricskai. "Chemistry of Biologically Important Hydroxylated Indolizidines Synthesis of Swainsonine, Castanospermine and Slaframine." In Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products Vol. 2, 751–828. Berlin, Heidelberg: Springer Berlin Heidelberg, 1993. http://dx.doi.org/10.1007/978-3-642-78250-3_16.

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Wang, Wei, Chiyi Xiong, Jiangqian Yang, and Victor J. Hruby. "Two Novel and Efficient Approaches to Synthesis of Enantiopure Dipeptide β-Turn Mimetics: Indolizidinone Amino Acids." In Peptides: The Wave of the Future, 30–31. Dordrecht: Springer Netherlands, 2001. http://dx.doi.org/10.1007/978-94-010-0464-0_9.

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Cluzeau, Jérôme, and William D. Lubell. "Mimicry of the Backbone and Side-Chain Geometry of Peptide Turns: Synthesis of Novel 4-Substituted Indolizidin-9-one Amino Acids." In Peptides: The Wave of the Future, 597–98. Dordrecht: Springer Netherlands, 2001. http://dx.doi.org/10.1007/978-94-010-0464-0_277.

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Colegate, S. M., and P. R. Dorling. "Bioactive Indolizidine Alkaloids." In Handbook of Plant and Fungal Toxicants, 1–18. CRC Press, 2020. http://dx.doi.org/10.1201/9780429281952-1.

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Michael, Joseph P. "Simple indolizidine and quinolizidine alkaloids." In The Alkaloids: Chemistry and Biology, 91–258. Elsevier, 2001. http://dx.doi.org/10.1016/s0099-9598(01)55004-x.

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Takahata, Hiroki, and Takefumi Momose. "Chapter 3 Simple Indolizidine Alkaloids." In The Alkaloids: Chemistry and Pharmacology, 189–256. Elsevier, 1993. http://dx.doi.org/10.1016/s0099-9598(08)60145-5.

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Michael, Joseph P. "Simple Indolizidine and Quinolizidine Alkaloids." In The Alkaloids: Chemistry and Biology, 1–498. Elsevier, 2016. http://dx.doi.org/10.1016/bs.alkal.2014.12.001.

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Lourenço, A. M., P. Máximo, L. M. Ferreira, and M. M. A. Pereira. "Indolizidine and quinolizidine alkaloids structure and bioactivity." In Bioactive Natural Products (Part H), 233–98. Elsevier, 2002. http://dx.doi.org/10.1016/s1572-5995(02)80038-2.

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Conference papers on the topic "Indolizidine"

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Bertonha, Ariane F., and Antonio C. B. Burtoloso*. "Studies aiming the synthesis of the indolizidine alkaloids (+)-Ipalbidine and (+)-Antofine." In 15th Brazilian Meeting on Organic Synthesis. São Paulo: Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-15bmos-bmos2013_201391415130.

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Pinho, Vagner D., and Antonio C. B. Burtoloso. "Diversity synthesis of indolizidine alkaloids from a,b- unsaturated diazoketones by the Wolff rearrangement." In 14th Brazilian Meeting on Organic Synthesis. São Paulo: Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-14bmos-r0128-1.

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Burtoloso, Antonio C. B. "α,β-Unsaturated Diazoketones as Useful Platforms in the Synthesis of Pyrrolidine, Piperidine and Indolizidine Alkaloids." In 15th Brazilian Meeting on Organic Synthesis. São Paulo: Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-15bmos-young5.

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Najera, Carmen, Tomas Abellan, Diego Alonso, Jesus Casas, Ana Costa, Jose Sansao, and Montserrat Varea. "(S)-5-(Tosylmethyl)-2-pyrrolidinone: A New Chiral b -Amidosulfone for a Short Asymmetric Synthesis of Indolizidines." In The 4th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2000. http://dx.doi.org/10.3390/ecsoc-4-01811.

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Santos, Airam O., José Tiago Menezes Correia, and Silvio Cunha. "Synthesis of pyrrolizidines, indolizidines and pyrroloazepines through formal aza-[3+3] and aza-[3+2] cycloadditions of enaminones with maleic anhydride and maleimides." In 14th Brazilian Meeting on Organic Synthesis. São Paulo: Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-14bmos-r0315-1.

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