Relevant bibliographies by topics / Stemona alkaloid

Academic literature on the topic 'Stemona alkaloid'

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Published: 4 June 2021
Last updated: 19 February 2022

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Journal articles on the topic "Stemona alkaloid"

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Yi, Min, Xue Xia, Hoi-Yan Wu, Hai-Yan Tian, Chao Huang, Paul Pui-Hay But, Pang-Chui Shaw, and Ren-Wang Jiang. "Structures and Chemotaxonomic Significance of Stemona Alkaloids from Stemona japonica." Natural Product Communications 10, no. 12 (December 2015): 1934578X1501001. http://dx.doi.org/10.1177/1934578x1501001221.

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A pair of new alkaloid stereo-isomers, stemocochinin (1) and isostemocochinin (2), was obtained from the roots of Stemona japonica Miq., along with seven known alkaloids, stemonamine (3), isostemonamine (4), maistemonine (5), isomaistemonine (6), croomine (7), stemonine (8), and protostemonine (9). The complete structure and stereochemistry of the pair of isomers were established by extensive analysis of the spectral data. Furthermore, our results indicated that S. japonica is chemically closer to S. sessilifolia than S. tuberosa, which are consistent with our previous DNA study on Stemona species.
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Sastraruji, Thanapat, Araya Jatisatienr, Kritchaya Issakul, Stephen G. Pyne, Alison T. Ung, Wilford Lie, and Morwenna C. Williams. "Phytochemical Studies on Stemona Plants: Isolation of New Tuberostemonine and Stemofoline Alkaloids." Natural Product Communications 1, no. 10 (October 2006): 1934578X0600101. http://dx.doi.org/10.1177/1934578x0600101001.

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Two new tuberostemonine alkaloids, tuberostemonine L (3) and tuberostemonine M (4) and a new stemofoline alkaloid, (3′S)-hydroxystemofoline (5), along with two known alkaloids, (2′S)-hydroxystemofoline (1) and neotuberostemonine (2) have been isolated from a root extract of an unidentified Stemona species (Stemona sp.). The structure and relative configuration of these new alkaloids has been determined by spectral data interpretation, while the 3′S configuration of 5 was determined from NMR analysis of its (R)- and (S)-Mosher esters.
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Wang, Peng, Hai Lin Qin, Zhi Hong Li, Ai Lin Liu, and Guan Hua Du. "A new alkaloid from Stemona sessilifolia." Chinese Chemical Letters 18, no. 2 (February 2007): 152–54. http://dx.doi.org/10.1016/j.cclet.2006.12.007.

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Chotikadachanarong, K., S. Dheeranupattana, and A. Jatisatienr. "MICROPROPAGATION AND ALKALOID PRODUCTION IN STEMONA SP." Acta Horticulturae, no. 676 (February 2005): 67–72. http://dx.doi.org/10.17660/actahortic.2005.676.7.

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Takeya, Koichi, Yukio Hitotsuyanagi, Maho Hikita, Kazuhiro Nakada, and Haruhiko Fukaya. "Sessilifoliamide I, a New Alkaloid from Stemona sessilifolia." HETEROCYCLES 71, no. 9 (2007): 2035. http://dx.doi.org/10.3987/com-07-11051.

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Lin, Li-Gen, Chun-Ping Tang, Pham-Huu Dien, Ren-Sheng Xu, and Yang Ye. "Cochinchistemonine, a novel skeleton alkaloid from Stemona cochinchinensis." Tetrahedron Letters 48, no. 9 (February 2007): 1559–61. http://dx.doi.org/10.1016/j.tetlet.2007.01.013.

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Wipf, Peter, Yuntae Kim, and David M. Goldstein. "Asymmetric Total Synthesis of the Stemona Alkaloid (-)-Stenine." Journal of the American Chemical Society 117, no. 45 (November 1995): 11106–12. http://dx.doi.org/10.1021/ja00150a010.

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Ramli, Rosdayati Alino, Wilford Lie, and Stephen G. Pyne. "Alkaloids from the Roots and Leaves of Stichoneuron halabalensis and their Acetylcholinesterase Inhibitory Activities." Natural Product Communications 8, no. 6 (June 2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800603.

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A study of the hitherto unreported Stichoneuron halabalensis Inthachub led to the characterization of the known compounds (+)-α-tocopherol and ( R)-(+)-goniothalamin; four known Stemona alkaloids, bisdehydoxystemoninine A (1), stemoninine (2), sessilistemonamine C (3) and sessilistemonamine A (4); and three new alkaloids, stichoneurine C (5), D (6) and E (7). The structures of these compounds were determined on the basis of their spectroscopic data. Alkaloid 7 showed significant inhibitory activity against electric eel acetylcholinesterase (AChE) (IC50 5.90±0.084 μM), while goniothalamin and compounds 1 and 2 showed significant inhibitory activities against human AChE (IC50 7.24±0.52, 5.52±0.13 and 3.74±0.09 μM, respectively).
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WIPF, P., Y. KIM, and D. M. GOLDSTEIN. "ChemInform Abstract: Asymmetric Total Synthesis of the Stemona Alkaloid (-)-Stenine." ChemInform 27, no. 13 (August 12, 2010): no. http://dx.doi.org/10.1002/chin.199613247.

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Morimoto, Yoshiki, Maki Iwahashi, Takamasa Kinoshita, and Koji Nishida. "ChemInform Abstract: Stereocontrolled Total Synthesis of the Stemona Alkaloid (-)-Stenine." ChemInform 33, no. 9 (May 22, 2010): no. http://dx.doi.org/10.1002/chin.200209221.

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Dissertations / Theses on the topic "Stemona alkaloid"

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Beck, Daniel Antony Speedie, and beckautomatic@gmail com. "Stereoselective intramolecular Michael addition reactions of pyrrole and their application to natural product syntheses." The Australian National University. Research School of Chemistry, 2006. http://thesis.anu.edu.au./public/adt-ANU20070130.130009.

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Chapter one; “(-)-Rhazinilam and (-)-Rhazinal: Alkaloids with Anti-mitotic Properties Derived from Kopsia teoi”, provides the background information behind the motives that initiated this research project. The plant alkaloid (-)-rhazinilam [(-)-1] and its naturally-occurring derivative (-)-rhazinal [(-)-13] both exhibit potent anti-mitotic activities and, as such, are interesting targets for total synthesis. Chapter one is a review of the literature regarding these two compounds and discusses the occurrence, proposed biosynthetic origins, structural elucidation and biological activites of compound (-)-1 and that of its analogues including alkaloid (-)-13. Previous total syntheses of these two compounds are then examined, concluding with the only reported total synthesis of compound (-)-13. Developed within the Banwell research group, this total synthesis produced the racemic modification of alkaloid (-)-13 due to a lack of any stereocontrol in the key intramolecular Michael addition step. This unprecedented key step, involving cyclisation of the C2 of pyrrole onto an N-tethered and ?,?-disubstituted acrylate to produce a quaternary-carbon stereogenic centre, would be of greatly enhanced utility if it could be achieved in a catalytic-enantioselective fashion. The realisation of this goal is the central aim of the research conducted within this thesis. ¶ Chapter two; “Investigating Asymmetric Induction in the Intramolecular Michael Addition of pyrrole to N-Tethered Acrylates and Related Species”, introduces the model study used to direct research towards achieving the goal of asymmetric induction in the title process. The model is a somewhat simplified version of the original process used in the total synthesis of compound (-)-13 involving cyclisation of the C2 of pyrrole onto an N-tethered and ?-monosubstituted Michael acceptor, to produce a tertiary-carbon stereogenic centre. This simplification allows the rapid synthesis of a broad range of potential substrates for use in the title process, thus enabling the investigation of various different approaches to inducing asymmetry therein. High levels of asymmetric induction are observed with the use of chiral substrates or catalysts, facilitating the synthesis of both 6- and 7-membered rings annulated to pyrrole with construction of the relevant tertiary-carbon stereogenic centre in enantio-enriched form. For the reactions producing a 6-membered ring annulated to pyrrole, unambiguous proof of the absolute sense of asymmetric induction observed in the intramolecular Michael addition event is established using a chemical correlation study involving elaboration of a key indolizine-type cyclisation product, to the plant alkaloid of known absolute stereochemistry, (-)-tashiromine [(-)-75]. For the reaction producing a 7-membered ring annulated to pyrrole, the same information is obtained via X-ray crystallographic analyses of a dibrominated derivative of a key pyrroloazepine-type cyclisation product. ¶ Chapter three “An Enantioselective Total Synthesis of the Alkaloid (-)-Rhazinal: An Anti-mitotic Agent Isolated from Kopsia teoi.”, focuses on the application of methodology developed in the previous chapter, to the original goal of inducing asymmetry in the intramolecular Michael addition reaction, involving cyclisation of the C2 of pyrrole onto an N-tethered and ?,?-disubstituted acrylate to produce a quaternary-carbon stereogenic centre. This is ultimately achieved in a catalytic-enantioselective fashion, resulting in the first such total synthesis of the anti-mitotic alkaloid (-)-rhazinal [(-)-13]. ¶ Chapter four “Extending the Reaction Manifold to the Syntheses of Related Natural Products: A Formal Total Synthesis of (+)-Aspidospermidine and Syntheses of (-)-Rhazinilam and (-)-Leuconolam from (-)-Rhazinal”, describes three extensions to the reaction manifold used in the enantioselective total synthesis of alkaloid (-)-13: The acquisition in an enantioselective manner, of an intermediate previously obtained in racemic form, en route to the racemic modification of the natural product (±)-aspidospermidine [(±)-134], constitutes a formal and enantioselective total synthesis of (+)-aspidospermidine [(+)-134]. The direct deformylation of (-)-rhazinal [(-)-13], is carried out, to produce the parent alkaloid (-)-rhazinilam [(-)-1]. The pyrrole ring present in (-)-rhazinilam [(-)-1] is oxidised, to produce the related natural product (-)-Leuconolam [(-)-12] which has not, hitherto, been prepared by total synthesis. ¶Chapter five contains the experimental procedures and characterisation data associated with compounds described in chapters two to four.
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Medley, Marcus I. "Studies Towards the Total Synthesis of Stemona Alkaloids." Thesis, University of Bristol, 2009. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.521103.

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Roe, Stephen. "Efficient approaches to the anatoxin & stemona alkaloids." Thesis, University of East Anglia, 2007. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.445212.

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Connelly, Rickki L. "Protecting group free approaches to the synthesis of stemona alkaloids." Thesis, University of Bristol, 2013. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.653083.

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Early, Craig. "Palladium catalysed routes to the trycycle core of the stemona alkaloids." Thesis, Loughborough University, 2007. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.479321.

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Leybourne, Danial. "Palladium-catalysed routes to the tricyclic core of the Stemona alkaloids." Thesis, Loughborough University, 2006. https://dspace.lboro.ac.uk/2134/34207.

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Heterocyclic product families include a wide and diverse range of natural and synthetic molecules, which exhibit a variety of biological activities. In particular this study will focus on the construction of the Stemona alkaloids, isolated from the roots and rhizomes of the Stemonaceae plant family. They possess the structurally novel and unique azepinoindole skeleton "B,C,D ring system." Studies towards the development of a novel methodology has been achieved. During our investigation we have developed a palladium(0)-catalysed [3+2]-cycloaddition strategy towards the rapid synthesis of heterocyclic skeletons, assembling polycyclic pyrrolidines and furan heterocycles from fused doubly activated vinylcyclopropanes. We have briefly investigated our palladium(0)-catalysed [3+2]-cycloaddition methodology towards doubly activated vinylcyclopropanes, preparing a selection of tetrahydrofuran and pyrrolidine precursors which underwent a Heck-mediated cyclisation. As well as further developing this methodology towards a tandem cycloaddition/Heck one-pot strategy. We hoped this initial ground work could be applied towards the construction of the tricyclic core of Stemona alkaloids.
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Bardají, Valls Núria. "Flexible Approach to Stemona Alkaloids: Total Syntheses of (–)-Stemospironine and Three New Diastereoisomeric Analogs." Doctoral thesis, Universitat Autònoma de Barcelona, 2013. http://hdl.handle.net/10803/113552.

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Neary, Vincent John. "Palladium catalysed 2 plus 3 cycloaddition routes to the trycyclic core of the stenine group of stemona alkaloids." Thesis, Loughborough University, 2007. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.479324.

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Brito, Júnior Gilmar Araújo 1986. "Estudos visando à síntese e determinação estrutural do alcalóide (-)-Parviestemoamida. Síntese formal do alcalóide (±)-Estemoamida e (±)-9a-epi-Estemoamida." [s.n.], 2014. http://repositorio.unicamp.br/jspui/handle/REPOSIP/249269.

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Orientador: Ronaldo Aloise Pilli
Tese (doutorado) - Universidade Estadual de Campinas, Instituto de Química
Made available in DSpace on 2018-08-26T22:32:16Z (GMT). No. of bitstreams: 1 BritoJunior_GilmarAraujo_D.pdf: 17782870 bytes, checksum: 5c94657b3c62d85cdf49bb3535c55ecb (MD5) Previous issue date: 2014
Resumo: Os alcaloides Estemona são um grupo de cerca de 170 substancias com características estruturais intrínsecas. Dentro desses compostos o alcaloide Parviestemoamida (11a/11b) foi isolado em 1991, mas não teve sua estrutura tridimensional elucidada. Através de estudos prévios no nosso grupo de pesquisa, um possível epímero para a estrutura 11b proposta foi sintetizado, mas a não exatidão das análises espectroscópicas não permitiu a conclusão da elucidação estrutural para esse composto. Diversas metodologias foram testadas visando à preparação da lactama de 10 membros em 48, 52 e 57, mas esses produtos nunca foram obtidos. Mudança no plano sintético foi feito baseado em construir inicialmente o anel de 10 membros e por fim o de 5 membros. Dessa maneira, através da reação de ciclização radicalar foi possível sintetizar o composto 92, já contendo todos os átomos de carbono presentes na estrutura proposta 11a/11b, porém não foi possível a funcionalização da ligação dupla nesse composto, por nenhuma das metodologias testadas. Utilizando-se de ferramentas computacionais e análises comparativas com o produto natural Estemoamida (17), sugerimos que o produto natural isolado por Xu e colaboradores é a própria Estemoamida (17) ou algum isômero. O outro alcaloide, Estemoamida (17) já teve sua estrutura tridimensional elucidada bem como foi objeto de várias sínteses totais. A hidrogenólise seguido de ciclização em cascata do intermediário 51a levou favorecidamente à estrutura tricíclica presente no alcaloide 9a-epi-Estemoamida (96b) com razão de 5:1. Através desses resultados variações nas condições reacionais, como pressão e solvente, buscamos uma condição para que o triciclo presente no produto natural (17) fosse favorecido. A hidrogenólise seguido de ciclização em cascata do intermediário 51b sob 10 atm de pressão de hidrogênio e trifluoretanol como solvente, levou ao isômero desejado 96a com razão de 10:1. Cálculos computacionais foram utilizados buscando uma explicação para essa diferença de seletividade. A conversão dos triciclos 96a e 96b nos alcaloides (±)-Estemoamida e (±)-9a-epi-Estemoamida, já se encontra presente na literatura. Dessa maneira, realizamos uma síntese formal, curta e bastante eficiente para esses alcaloides
Abstract: The Stemona alkaloids are a group of about 170 substances that possess unique structural features. Among those compounds, Parviestemoamide (11a/11b) was isolated in 1991, but its tridimensional structure was not elucidated. Through previous studies in our research group, a possible epimer of the proposed structure 11b was synthetized, but the spectroscopic analysis did not match with the reported data, preventing an unambiguous structural elucidation of this compound. Several synthetic approaches toward the 10 membered lactam in 48, 52 and 57 were tested, but the desired products were never obtained in any condition tested. A alternative synthetic strategy to initially prepare the 10 membered ring and then the 5 membered lactone was planned. In this way, compound 92 was prepared by the radical cyclization reaction, already having all the carbon atoms present in the proposed structure 11a/11b, but unfortunately it was not possible to conduct the double bond functionalization in this bicyclic compound using the tested methodologies. Employing computational tools and by comparative analysis with the natural product Stemoamide (17), we suggest that the natural product isolated by Xu and coworkers is Stemoamide (17) itself or an isomer of 17. On the other hand, Stemoamide (17) already has had its tridimensional structure elucidated through syntheses by many research groups. The hydrogenolysis followed by cascade cyclization on intermediate 51a led to the core 96b present in 9a-epi-Estemoamida (98) and its 9a epimer in a 5:1 ratio, respectively. Inspired by this result, we sought a condition that could provide the other diastereomer, 96a, present in the natural Stemona alkaloid, Stemoamide (17). Based on this, the intermediate 51b was submitted to a similar condition, with 10 atm of H2 pressure and trifluoroethanol as solvent. In this way, the desired isomer 96a was obtained with 10:1 diastereoisomeric ratio. Computational calculations have been employed to explain this facial selectivity. The conversion of compounds 96a and 96b in the alkaloids (±)-Stemoamide (17) and (±)-9a-epi-Stemoamide (98) is already reported in the literature, so we could perform a short and efficient synthesis of these alkaloids
Doutorado
Quimica Organica
Doutor em Ciências
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Huang, Wen-Wei, and 黃文葦. "Synthetic Studies on Dendrobatid Alkaloids-223A,the Stemona Alkaloid”Allostemoamide”,and the Tremulane Sesquiterpenes, Tremulenolide Aby Rh-catalyzed Domino Cyclizations." Thesis, 2019. http://ndltd.ncl.edu.tw/handle/25x843.

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碩士
國立中興大學
化學系所
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We describe the application of Rh-catalyzed domino cycloaddition toward natural product of bicyclic alkaloid species. In the first part, we continue the research work of 2016: using tri-substituted alkene as nucleophile fused aza-bicyclic product. Based on previous result, we install C-6, C-8 position substitution respectively, complete the total syntheses of tri- substituted Dendrobatid alkaloid 223A and 6-epi-223A through different demonstrate. In the second part, we continue the research work of 2016、2017: prepare γ- position substituted precursors to carry on hydroformylation reaction, study on the difference between β- and γ- position substituted precursor of simultaneously, and synthetic study toward Stemona alkaloid, “Allostemoamide” though known aza-bicyclic compound. In the third part, we study on Rh-catalyzed cycloaddition of endiyne precursor to fused the perhydroazulene skeleton of Tremulane Sesquiterpenes, Tremulenolide A.
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Book chapters on the topic "Stemona alkaloid"

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Taber, Douglass F. "Alkaloid Synthesis: Indolizidine 223AB (Cha), Lepadiformine (Kim), Kainic Acid (Fukuyama), Gephyrotoxin (Smith), Premarineosin A (Reynolds)." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0059.

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Jin Kun Cha of Wayne State University prepared (Org. Lett. 2014, 16, 6208) the allene 1 by SN2′ coupling of a cyclopropanol with a propargylic tosylate. Silver-mediated cyclization converted 1 into 2, that was reduced with diimide to the Dendrobates alka­loid indolizidine 223AB 3. Sanghee Kim of Seoul National University observed (Chem. Eur. J. 2014, 20, 17433) high diastereoselectivity in the Ireland–Claisen rearrangement of 4 to 5. The acid 5 was the key intermediate for the synthesis of the tunicate alkaloid lepadiformine 6. Tohru Fukuyama of Nagoya University also used (Eur. J. Org. Chem. 2014, 4823) an ester enolate Claisen rearrangement to set the relative and absolute configuration of 7. Pd-catalyzed cyclization then led to 8, that was carried on to the excitatory amino acid receptor agonist kainic acid 9. Gephyrotoxin 12 was so named because it incorporates structural elements from two different classes of the Dendrobates alkaloids. Martin D. Smith of the University of Oxford envisioned (Angew. Chem. Int. Ed. 2014, 53, 13826) the cascade cyclization of deprotected 10 to give, after reduction, the ketone 11. Zhen Yang of the Peking University Shenzhen Graduate School showed (Chem. Eur. J. 2014, 20, 12881) that the Rh carbene derived from 13 readily cyclized to an imine. The facial selectivity of the addition of the Grignard reagent 14 to that imine depended on the temperature of the reaction. At room temperature, 15 was formed. At low temperature, the other diastereomer predominated. Ring-closing metathesis was used for the elaboration of 15 to the Stemona alkaloid tuberostemospiroline 16. Kevin A. Reynolds of Portland State University prepared (J. Org. Chem. 2014, 79, 11674) 19 by condensation of the pyrrole 17 with the aldehyde 18. The biosyn­thetic enzyme, that they had overexpressed, oxidized 19 to the antimalarial alkaloid permarineosin A 20.
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Pilli, Ronaldo A., Giovanni B. Rosso, and Maria Da Conceição F. De Oliveira. "The Stemona Alkaloids." In The Alkaloids: Chemistry and Biology, 77–173. Elsevier, 2005. http://dx.doi.org/10.1016/s1099-4831(05)62002-0.

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Conference papers on the topic "Stemona alkaloid"

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HENRIQUE GONCALVES DEFANTE, LUIS, and Ronaldo Aloise Pilli. "Synthesis of a pyrrolo[1,2-a]azepino ring aiming the synthesis of Stemona alkaloids." In XXV Congresso de Iniciação Cientifica da Unicamp. Campinas - SP, Brazil: Galoa, 2017. http://dx.doi.org/10.19146/pibic-2017-78501.

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