Academic literature on the topic 'Piperidine alkaloid synthesis'

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Journal articles on the topic "Piperidine alkaloid synthesis"

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Enders, Dieter, and Christoph Thiebes. "Efficient stereoselective syntheses of piperidine, pyrrolidine, and indolizidine alkaloids." Pure and Applied Chemistry 73, no. 3 (2001): 573–78. http://dx.doi.org/10.1351/pac200173030573.

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Recent advances in the diastereo- and enantioselective synthesis of piperidine, pyrrolidine, and indolizidine alkaloids, based on the highly stereoselective 1,2-addition to the CN double bond of chiral aldehyde-SAMP/RAMP hydrazones, are described. The enantioselective syntheses of the pyrrolidine alkaloids bgugaine and (2S,12¢R)-2-(12¢-aminotridecyl)-pyrrolidine, a defense alkaloid of the Mexican bean beetle are reported. Furthermore, the SAMP/RAMP-hydrazone method was applied to the syntheses of two 5,8-disubstituted indolizidine alkaloids that have been extracted from neotropical poison-dart
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Mill, Sibel, and Claude Hootelé. "A revised structure for the piperidine alkaloid andrachamine." Canadian Journal of Chemistry 74, no. 12 (1996): 2434–43. http://dx.doi.org/10.1139/v96-272.

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A new method for the synthesis of trans-2,6-disubstituted piperidine derivatives is described. The transformation of cyclic α-methoxycarbamates 5 and 6 affords trans ketones 17 and 18. The synthesis of diols 1–4 from 17 and 18 has shown that the structure proposed in the literature for the piperidine alkaloid andrachamine is incorrect. A reexamination of the original spectral data of this alkaloid suggested that it is a meso 2,6-disubstituted piperidine derivative. Unambiguous syntheses of 23 and 24 and comparison with a sample of andrachamine have established that this alkaloid possesses stru
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Bonandi, Elisa, Giada Tedesco, Dario Perdicchia, and Daniele Passarella. "Total Synthesis of (–)-Anaferine: A Further Ramification in a Diversity-Oriented Approach." Molecules 25, no. 5 (2020): 1057. http://dx.doi.org/10.3390/molecules25051057.

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The piperidine ring is a widespread motif in several natural bioactive alkaloids of both vegetal and marine origin. In the last years, a diversity-oriented synthetic (DOS) approach, aimed at the generation of a library of piperidine-based derivatives, was developed in our research group, employing commercially available 2-piperidine ethanol as a versatile precursor. Here, we report the exploration of another ramification of our DOS approach, that led us to the stereoselective total synthesis of (–)-anaferine, a bis-piperidine alkaloid present in Withania somnifera extract. This natural product
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Raji Reddy, Chada, Bellamkonda Latha, Kamalkishor Warudikar, and Kiran Kumar Singarapu. "Total synthesis of a piperidine alkaloid, microcosamine A." Organic & Biomolecular Chemistry 14, no. 1 (2016): 251–58. http://dx.doi.org/10.1039/c5ob02085a.

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Sartillo-Piscil, Fernando, Julio Romero-Ibañez, Silvano Cruz-Gregorio, and Leticia Quintero. "Concise and Environmentally Friendly Asymmetric Total Synthesis of the Putative Structure of a Biologically Active 3-Hydroxy-2-piperidone Alkaloid." Synthesis 50, no. 15 (2018): 2878–86. http://dx.doi.org/10.1055/s-0037-1610089.

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An asymmetric total synthesis of stereoisomers of a putative structure of 3-hydroxy-2-piperidone alkaloid derivative is described. This route is not only concise and efficient but also is achieved under an environmentally friendly approach. To this end, a direct and double C–H oxidation reaction of simple benzylated piperidine and Baker’s yeast reduction of a carbonyl group allowed the rapid access to the optically enriched (S)-1-benzyl-3-hydroxy-2-piperidone in only three steps. The NMR data agreed with those obtained in the first total synthesis (and in discrepancy with the natural product),
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Sośnicki, Jacek G., and Tomasz J. Idzik. "Pyridones – Powerful Precursors for the Synthesis of Alkaloids, Their Derivatives, and Alkaloid-Inspired Compounds." Synthesis 51, no. 18 (2019): 3369–96. http://dx.doi.org/10.1055/s-0037-1611844.

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2-Pyridone is characterized by a very wide range of reactivity of a different nature, ranging from electrophilic aromatic substitution, CH–metal-mediated reactions, and NH/OH functionalization of both possible lactam/lactim tautomers, through cycloaddition, to nucleophilic addition and transformation of the tautomeric C=O/C–OH moiety. The high availability of 2-pyridones and the possibility of their far-reaching functionalization additionally increased their values. Therefore, they are very useful building blocks for the synthesis of structurally diverse piperidine and pyridine compounds, incl
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Denic, Marija, Polina Blagojevic, and Niko Radulovic. "Synthetic approaches to coniine and other 2-alkyl piperidines." Facta universitatis - series: Physics, Chemistry and Technology 11, no. 1 (2013): 1–26. http://dx.doi.org/10.2298/fupct1301001d.

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The first synthesis of coniine, a neurotoxic piperidine alkaloid found in poison hemlock (Conium maculatum L.), was performed back in 1886 by Ladenburg. Since that time, numerous different approaches to the synthesis of this and related alkaloids (2-alkylpiperidines) have been developed. Nowadays, the enantioselective/specific synthesis of coniine is taken as a paradigm of the usefulness of new chiral synthetic methodologies. This review aims to summarize and systematize recent progress in the synthesis of coniine and related compounds.
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Bell, Jonathan D., Alexander H. Harkiss, Christopher R. Wellaway, and Andrew Sutherland. "Stereoselective synthesis of 2,6-trans-4-oxopiperidines using an acid-mediated 6-endo-trig cyclisation." Organic & Biomolecular Chemistry 16, no. 35 (2018): 6410–22. http://dx.doi.org/10.1039/c8ob01363b.

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An acid-mediated 6-endo-trig cyclisation has been developed for the synthesis of trans-6-alkyl-2-methyl-4-oxopiperidines and used for the stereoselective preparation of quinolizidine alkaloid, (+)-myrtine and the piperidine alkaloid, (−)-solenopsin A.
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Suzuki, Kana, Yasunao Hattori, Atsushi Kawamura, and Hidefumi Makabe. "Synthesis of (+)-solenopsin via Pd-catalyzed N-alkylation and cyclization." Bioscience, Biotechnology, and Biochemistry 85, no. 2 (2021): 223–27. http://dx.doi.org/10.1093/bbb/zbaa014.

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ABSTRACT Synthesis of (+)-solenopsin, a 2,6-disubstituted piperidine alkaloid, isolated from fire ants (Solenopsis), was achieved. Stereoselective construction of trans-2,6-piperidine ring moiety was performed using palladium-catalyzed cyclization. Chain elongation using Grubbs 2nd catalyst followed by the reduction of double bond and the deprotection of the Cbz group afforded (+)-solenopsin.
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Plehiers, Mark, та Claude Hootelé. "Synthesis of β-hydroxypiperidine alkaloids by anodic oxidation of carbamates and hydroboration". Canadian Journal of Chemistry 74, № 12 (1996): 2444–53. http://dx.doi.org/10.1139/v96-273.

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The β-hydroxypiperidine alkaloids (±)-pseudoconhydrine, (±)-N-methylpseudoconhydrine, (−)-5-hydroxysedamine, and (+)-sedacryptine were synthesized. Successive functionalization of the piperidine ring via anodic methoxylation allowed the regio- and stereoselective introduction of the substituents. The α and α′ substituents were introduced by application of the sequence elimination–nucleophilic addition from 2- or 2,5-substituted 6-methoxycarbamates. Hydroboration – oxidation of enecarbamates, obtained by elimination of methanol from α-methoxycarbamates, allowed the introduction of the β-hydroxy
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Dissertations / Theses on the topic "Piperidine alkaloid synthesis"

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Mosts, R. C. "Studies in the synthesis of piperidine alkaloids." Thesis, University of Essex, 1987. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.379495.

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Smith, Peter Duncan. "Synthesis of pipecolic acid derivatives via aza-Diels-Alder reactions." Thesis, Heriot-Watt University, 2000. http://hdl.handle.net/10399/552.

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Vu, Van Ha. "Cyanation anodique et réaction de Fry modifiée : application à la synthèse stéréosélective d’alcaloïdes de la pipéridine." Thesis, Rennes 1, 2014. http://www.theses.fr/2014REN1S138/document.

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Les alcaloïdes de la pipéridine sont des composés présents à la fois dans le règne animal et végétal. L'approche générale que nous avons développée au cours de ce travail de thèse est basée sur l'utilisation de différents -aminonitriles qui ont été préparés soit par réduction de sels de pyridinium chiraux soit par cyanation anodique d'amines tertiaires dérivées de l'-phényl-éthylamine. Dans le premier cas, la modification de la réaction de Fry nous a permis de préparer les deux énantiomères de la coniine qui constitue l'agent toxique de la grande cigüe (Conium maculatum). En combinant cette mé
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Adams, David Roger. "Studies in the synthesis of piperidine alkaloids." Thesis, University of Exeter, 1990. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.236570.

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Coggins, P. "Syntheses with 2-alkyl-2,3,4,5-tetrahydropyridine-1-oxides." Thesis, University of Exeter, 1989. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.235969.

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Rosset, Isac George. "Diazocetonas α,β-insaturadas como reagentes multifuncionais: aplicação na síntese de alcaloides piperidínicos e pirrolidínicos." Universidade de São Paulo, 2015. http://www.teses.usp.br/teses/disponiveis/75/75133/tde-20052015-101409/.

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p>O primeira parte do trabalho descreve a preparação de um novo reagente de olefinação de HWE para o preparo de diazocetonas α, β-insaturadas com geometria Z e aplicação na síntese de núcleos piperidínicos funcionalizados. Através da otimização da reação de HWE empregando o benzaldeído como aldeído padrão foi possível maximizar a obtenção do isômero Z desejado (92%, Z:E 9:1). As reações-chave para a formação dos núcleos piperidínicos foram a de olefinação de HWE utilizando amino-aldeídos, obtendo-se bons rendimentos e boa seletividade, seguida de uma reação de inserção N-H catalisad
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Archibald, Glenn Philip. "Use of novel nitrones in the synthesis of piperidine alkaloids." Thesis, University of Auckland, 2011. http://hdl.handle.net/2292/7127.

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The current study focused on development of a flexible synthetic strategy for the enantioselective preparation of 2-substituted-3-hydroxypiperidines utilising chiral 3-hydroxytetrahydropyridine N-oxides. Initial studies into the regio- and stereoselectivity of the 1,3-dipolar cycloaddition reaction between O-benzyl protected 3-hydroxytetrahydropyridine N-oxide 208 and a range of alkenes, proceeded with excellent exo/endo selectivity and near perfect regioselectivity. However the anti/syn selectivity was only moderately in favour of the desired anti-compounds. Further development has led to the
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Moore, Rebecca J. "Novel approaches to natural product synthesis using organozinc intermediates." Thesis, University of Newcastle Upon Tyne, 1997. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.362516.

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Lansakara, Ashabha Indrashika. "Intramolecular cyclizations of alkyl pyridines & alkylidene dihydropyridines as synthetic intermediates toward synthesis of bis(piperidine) alkaloids." Diss., University of Iowa, 2016. https://ir.uiowa.edu/etd/2105.

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Nature provides fascinating and complicated molecular structures which offer synthetic organic chemists amazing opportunities for the design of new strategies for natural product synthesis. Among these, nitrogen containing aza-heterocycles are of unparalleled importance in natural product, bioorganic, and medicinal chemistry. Pyridine and its derivatives in particular are the most common aza-heterocycles encountered in natural products, medicinal and materials chemistry. Pyridine derivatives also serve as precursors to fun
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Eriksson, Carina. "Isolation, Synthesis and Structure-Activity Relationships of Antifeedants against the Pine Weevil, Hylobius Abietis." Doctoral thesis, Stockholm Chemical Science and Engineering, KTH, 2006. http://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-3919.

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Book chapters on the topic "Piperidine alkaloid synthesis"

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Taber, Douglass. "The Smith Synthesis of ( + )-Lyconadin A." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0086.

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The pentacyclic alkaloid ( + )-lyconadin A 3, isolated from the club moss Lycopodium complanatum, showed modest in vitro cytotoxicity. A key step in the first reported (J. Am. Chem. Soc. 2007, 129, 4148) total synthesis of 3, by Amos B. Smith III of the University of Pennsylvania, was the cyclization of 1 to 2. The pentacyclic alkaloid (+)-lyconadin A 3, isolated from the club moss Lycopodium complanatum, showed modest in vitro cytotoxicity. A key step in the first reported (J. Am. Chem. Soc. 2007, 129, 4148) total synthesis of 3, by Amos B. Smith III of the University of Pennsylvania, was the cyclization of 1 to 2. The pentacyclic skeleton of 3 was constructed around a central organizing piperidine ring 9. This was prepared from the known (and commercial) enantiomerically-pure lactone 4. The akylated stereogenic center of 9 was assembled by diastereoselective hydroxy methylation of the acyl oxazolidinone 5 with s-trioxane, followed by protection. Reduction of the imide to the alcohol led to the mesylate 7, which on reduction of the azide spontaneously cyclized to give, after protection, the piperidine 8. Selective desilylation of the primary alcohol then enabled the preparation of 9. The plan was to assemble the first carbocyclic ring of 3 by intramolecular aldol condensation of the keto aldehyde 15. The enantiomerically-pure secondary methyl substituent of 15 derived from the commercial monoester 10. Activation as the acid fluoride followed by selective reduction led to the volatile lactone 11. Opening of the lactone with H3CONHCH3HCl gave, after protection, the Weinreb amide 12. Alkylation of the derived hydrazone 13, selectively on the methyl group, led, after deprotection, to 15. The intramolecular aldol condensation of 15 did deliver the unstable cyclohexenone 1. Under the acidic conditions of the aldol condensation, the enol derived from the piperidone added in a Michael sense, from the axial direction on the newly-formed ring, to give the trans-fused bicyclic diketone 2.
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Taber, Douglass F. "Alkaloid Synthesis: (+)-Deoxoprosopinine (Krishna), Alkaloid (–)-205B (Micalizio), FR901483 (Huang), (+)-Ibophyllidine (Kwon), (–)-Lycoposerramine-S (Fukuyama), (±)-Crinine (Lautens)." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0060.

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Palakodety Radha Krishna of the Indian Institute of Chemical Technology observed (Synlett 2012, 2814) high stereocontrol in the addition of allyltrimethylsilane to the cyclic imine derived from 1. The product piperidine 2 was carried onto (+)-deoxoprosopinine 3. Glenn C. Micalizio of Scripps Florida condensed (J. Am. Chem. Soc. 2012, 134, 15237) the amine 4 with 5. The ensuing intramolecular dipolar cycloaddition led to 6, which was carried onto the Dendrobates alkaloid (–)-205B 7. Pei-Qiang Huang of Xiamen University showed (Org. Lett. 2012, 14, 4834) that the quaternary center of 9 could be established with high diastereoselectivity by activation of the lactam 8, then sequential addition of two different Grignard reagents. Subsequent stereoselective intramolecular aldol condensation led to FR901843 10. More recently, Professor Huang, with Hong-Kui Zhang, also of Xiamen University, published (J. Org. Chem. 2013, 78, 455) a full account of this work. In an elegant application of the power of phosphine-catalyzed intermolecular allene cycloaddition, Ohyun Kwon of UCLA added (Chem. Sci. 2012, 3, 2510) 12 to the imine 11 to give 13. The cyclization elegantly set two of the four stereogenic centers of (+)-ibophyllidine 14. Tohru Fukuyama of the University of Tokyo initiated (Angew. Chem. Int. Ed. 2012, 51, 11824) a cascade cyclization between the enone 15 and the chiral auxiliary 16. The product lactam 17 was carried onto (–)-lycoposerramine-S 18. Mark Lautens explored (J. Am. Chem. Soc. 2012, 134, 15572) the utility of the intramolecular aryne ene reaction, as illustrated by the cyclization of 19 to 20. Oxidation cleavage of the vinyl group of 20 followed by an intramolecular carbonyl ene reaction led to (±)-crinine 21.
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Taber, Douglass F. "Synthesis of C-N Natural Products: (-)-α-Kainic Acid (Helmchen), (+)-Tylophorine (Opatz), (-)-Lycoperine A (Rychnovsky), Fluvirucidine A2 (Suh), Complanidine A (Sarpong)." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0058.

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Günter Helmchen of the Ruprecht-Karls-Universität Heidelberg set (Organic Lett. 2010, 12, 1108) the absolute configuration of 3 by Ir*-mediated coupling of 1 with 2. Diastereoselective Pauson-Khand cyclization then led to (-)-α-kainic acid 5. Till Opatz, now at the Johannes Gutenberg-Universität Mainz, showed (Organic Lett. 2010, 12, 2140) that the product from the Dibal reduction of 6 could be condensed with the amine 7 without epimerization. Kim cyclization then directly delivered the pentacyclic alkaloid (+)-tylophorine 9. The interesting dimeric alkaloid lycoperine A 13 was recently isolated from the Japanese club moss Lycopodium hamiltonii. Scott D. Rychnovsky of the University of California, Irvine, prepared (Organic Lett. 2010, 12, 72) 12 by double alkylation of the bis-nitrile 11 with the enantiomerically pure allylic bromide 10. Although the projected reductive decyanation of 12 failed, hydrolysis followed by diastereoselective reductive amination successfully gave 13. Retrosynthetic analysis of fluvirucinine A2 16 could lead to an acyclic amino acid, which could be cyclized to the macrolactam. Young-Ger Suh of Seoul National University took (Organic Lett. 2010, 12, 2040) a different approach, building up the 14-membered ring system by two four-carbon ring expansions, beginning with an enantiomerically pure piperidine precursor. The second of these enolate-based aza-Claisen ring expansions is illustrated in the conversion of 14 to 15. Richmond Sarpong of the University of California, Berkeley, faced (J. Am. Chem. Soc. 2010, 132, 5926) a different sort of challenge in the synthesis of the dimeric Lycopodium alkaloid complanadine A 19. Even with established access to monomers such as 17 and its precursors, it was not clear how the 5-position of the pyridine ring could be selectively activated for bond formation. The solution to this dilemma was found in the work of Hartwig. Following that precedent, Ir-catalyzed activation of 17 converted it cleanly into the borinate 18, which could then be coupled with a pyridone triflate to complete the synthesis of 19.
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Taber, Douglass F. "The Snyder Synthesis of Psylloborine A." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0099.

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In addition to the monomeric coccinellid alkaloids produced by the ladybug, some dimeric alkaloids, exemplified by psylloborine A 3, have been isolated. Scott A. Snyder of Scripps/Florida initially attempted a direct dimerization strategy for the assembly of 3, but when that failed, he devised (J. Am. Chem. Soc. 2014, 136, 9743) a route to the tethered dimer 1, that could indeed be cyclized to 2, the immediate precursor to 3. The starting material for both 9, the lower half of 1, and 13, the upper half of 1, was the commercial, enantiomerically-pure piperidine 4. Metalation followed by allylation gave the desired trans diastereomer 5. Oxidative cleavage followed by con­densation with 6 gave the ester 7, that was hydrogenated, then converted with 8 to the desired phosphonate 9. To prepare 13, 4 was metalated and alkylated with methallyl bromide. The prod­uct 10 was carried on to the enone 12 by oxidative cleavage followed by the addition of 11, oxidative cleavage, and dehydration. Reduction to the desired diastereomer was achieved by conjugate addition of hydride in the presence of the sterically very demanding Yamamoto Lewis acid ATPH. Deprotection followed by oxidation then gave 13, that was condensed with 9 and deprotected to give 14. Selective deprotection followed by oxidation and condensation with 15 then led to 1. A key element in the design of this synthesis was the ability to easily tune the sul­fone activating group, to direct the proper order of bond formation. The vision was that regeneration of the enone and deprotection, with tetramethylguanidine, would lead to 16. The free amine would add to the saturated ketone to give an enamine, that would in turn add in a conjugate sense to the enone to give 17. Further deprotec­tion of 17 under acid conditions would again generate an enamine that, it was hoped, would, after further cyclization, add to the unsaturated sulfone to give 2. As illustrated, the 3,5-bis(trifluoromethyl)phenyl sulfone gave the best results. Desulfurization of 2 completed the synthesis of the complex dimeric alkaloid psylloborine A 3.
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Angle, S. R., and J. G. Breitenbucher. "Recent progress in the synthesis of piperidine and indolizidine alkaloids." In Stereoselective Synthesis (Part J). Elsevier, 1995. http://dx.doi.org/10.1016/s1572-5995(06)80060-8.

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Ojima, Iwao, and Donna M. Iula. "New Approaches to the Syntheses of Piperidine, Izidine, and Quinazoline Alkaloids by Means of Transition Metal Catalyzed Carbonylations." In Alkaloids: Chemical and Biological Perspectives. Elsevier, 1999. http://dx.doi.org/10.1016/s0735-8210(99)80028-4.

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Conference papers on the topic "Piperidine alkaloid synthesis"

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

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