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Journal articles on the topic 'Synthesis of alkaloids'

Author: Grafiati

Published: 4 June 2021

Last updated: 16 February 2022

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1

Han, Sunkyu, Sangbin Jeon, and Joonoh Park. "Syntheses of Dimeric Securinega Alkaloids." Synlett 28, no. 18 (2017): 2353–59. http://dx.doi.org/10.1055/s-0036-1590864.

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The isolation of flueggenines A and B by Yue and co-workers in 2006 has triggered a burst of isolation reports of dimeric and oligomeric securinega alkaloid natural products. The compelling molecular structures of these compounds with various modes of connection between monomeric securinega units have posed intriguing challenges to the synthetic organic community. Herein, we have categorized high-order securinega alkaloids based on their biosynthetic mode of dimerization or oligomerization. We then have compiled all reported syntheses of dimeric securinega alkaloids based on our classification

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2

Lim, Hyeonggeun, Sikwang Seong, and Sunkyu Han. "Syntheses of Post-Iboga Alkaloids." Synthesis 51, no. 14 (2019): 2737–58. http://dx.doi.org/10.1055/s-0037-1612061.

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Post-iboga alkaloids are secondary metabolites that are biosynthetically derived from iboga-type alkaloids via rearrangements of the indole and/or isoquinuclidine moieties. Herein, we categorize post-iboga alkaloids into five types based on the biosynthetic mode of transformation of the iboga scaffold. We then describe reported syntheses of post-iboga alkaloids, including our laboratory’s recent contributions, based on our own categorization.1 Introduction1.1 Iboga and Post-Iboga Alkaloids1.2 Classification of Post-Iboga Alkaloids1.2.1 Introduction to Type I Post-Iboga Alkaloids1.2.2 Introduct

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3

Saha, Mrinmoy, and Rich Carter. "Lycopodium Alkaloids: An Intramolecular Michael Reaction Approach." Synlett 28, no. 17 (2017): 2212–29. http://dx.doi.org/10.1055/s-0036-1588851.

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The Lycopodium alkaloids possess a rich history that has captured the attention of synthetic chemists across the globe. This large family consists of over 250 known natural products with diverse structural features and noteworthy biological activity. Herein, we interweave the synthetic accomplishments by others in the field with our own unified strategy to accessing multiple subfamilies of the Lycopodium alkaloids. This discussion includes lycopodine, the C10-hydroxy Lycopodium alkaloids (10-hydroxylycopodine, deacetylpaniculine and paniculine), pelletierine, cermizine D, fastigiatine, himerad

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4

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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5

Giannis, Athanassios, Farnoush Mousavizadeh, and Daniel Meyer. "Synthesis of C-Nor-D-homo-steroidal Alkaloids and Their Derivatives." Synthesis 50, no. 08 (2018): 1587–600. http://dx.doi.org/10.1055/s-0036-1591965.

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The C-nor-D-homo-steroidal alkaloid cyclopamine was discovered in the 1969 and in 2000 it was shown to act as an inhibitor of the hedgehog signaling (Hh) pathway, which is aberrantly activated in some tumors. Subsequently it was revealed that this natural occurring alkaloid has also antidiabetic and antiviral properties. In this review we present syntheses of selected C-nor-D-homo-steroidal alkaloids and their analogues and also discuss a general access to C-nor-D-homo-steroids. Some historical as well as biomedical aspects are also presented.1 Introduction2 Total Synthesis of Cyclopamine2.1 S

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6

D’hooghe, Matthias, Hyun-Joon Ha, and Lingamurthy Macha. "Deployment of Aziridines for the Synthesis of Alkaloids and Their Derivatives." Synthesis 51, no. 07 (2019): 1491–515. http://dx.doi.org/10.1055/s-0037-1611715.

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Various (activated and non-activated) aziridines with diverse substitution patterns have been deployed successfully as starting materials for the synthesis of a wide variety of alkaloids via suitable functionalization and aziridine ring transformation. Alternatively, the preparation and interception of reactive aziridine intermediates has also been shown to constitute a valid approach toward alkaloid synthesis. This review summarizes aziridine-mediated syntheses of alkaloids, in which the aziridine is mobilized as either a substrate or an advanced synthetic intermediate.1 Introduction2 Alkaloi

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7

Wink, Michael, and Ludger Witte. "Cell-Free Synthesis of the Alkaloids Ammodendrine and Smipine." Zeitschrift für Naturforschung C 42, no. 3 (1987): 197–204. http://dx.doi.org/10.1515/znc-1987-0304.

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The bipiperidyl alkaloid ammodendrine was detected in 28 plant species as a minor alkaloid besides quinolizidine alkaloids. Cadaverine serves as a precursor for both quinolizidine alkaloids and for ammodendrine, since labelled cadaverine is incorporated into both rings of ammodendrine. Cell-free extracts of Lupinus arboreus and of Pisum sativum, which contain an active diamine oxidase form ammodendrine from cadaverine and pyruvate. In addition to ammodendrine other alkaloids such as smipine, tetrahydroanabasine and tripiperideine could be detected. Possible reaction schemes are discussed.

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8

Estévez, Juan C., M. Carmen Villaverde, Ramon J. Estévez, Julio A. Seuas, and Luis Castedo. "New total synthesis of phenanthrene alkaloids." Canadian Journal of Chemistry 68, no. 6 (1990): 964–68. http://dx.doi.org/10.1139/v90-151.

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We describe a new synthesis of phenanthrene alkaloids based on the photocyclization of stilbene compounds prepared by a simple, efficient new method. It allows the preparation of phenanthrene compounds with a primary amine group in their side chain. Keywords: alkaloid, phenanthrene, stilbene, photocyclization.

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9

Li, Yong, Jian Li, Hanfeng Ding, and Ang Li. "Recent advances on the total synthesis of alkaloids in mainland China." National Science Review 4, no. 3 (2017): 397–425. http://dx.doi.org/10.1093/nsr/nwx050.

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AbstractAlkaloids are a large family of natural products that mostly contain basic nitrogen atoms. Because of their intriguing structures and important functions, they have long been popular targets for synthetic organic chemists. China's chemists have made significant progress in the area of alkaloid synthesis over past decades. In this article, selected total syntheses of alkaloids from research groups in mainland China during the period 2011–16 are highlighted.

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10

Miyashita, Masaaki. "Recent progress in the synthesis of bioactive polycyclic natural products." Pure and Applied Chemistry 79, no. 4 (2007): 651–65. http://dx.doi.org/10.1351/pac200779040651.

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The zoanthamine alkaloids, a type of heptacyclic marine alkaloid isolated from colonial zoanthids of the genus Zoanthus sp., have distinctive biological and pharmacological properties as well as their unique chemical structures with stereochemical complexity. Namely, norzoanthamine can suppress the loss of bone weight and strength in ovariectomized mice and has been considered a promising candidate for an antiosteoporotic drug, whereas zoanthamine has exhibited potent inhibitory activity toward phorbol myristate-induced inflammation in addition to powerful analgesic effects. Recently, norzoant

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11

Czarnocki, Zbigniew, David B. MacLean, and Walter A. Szarek. "Enantioselective synthesis of isoquinoline alkaloids: phenylethylisoquinoline and aporphine alkaloids." Canadian Journal of Chemistry 65, no. 10 (1987): 2356–61. http://dx.doi.org/10.1139/v87-393.

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A new and improved procedure for the preparation of (R)-2-alkoxycarbonyl-1-formyl-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinolines has been developed beginning from D-(−)-tartaric acid. The utility of these aldehydes in the asymmetric synthesis of isoquinoline alkaloids of high enantiomeric purity has been extended to the synthesis of phenylethylisoquinolines, which have been further transformed in straightforward steps into the homoprotoberberine and homoaporphine ring systems. In this manner, (S)-homolaudanosine, (S)-5′-methoxyhomolaudanosine, (S)-2,3,9,10,11-pentamethoxyhomoprotoberberine, and

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12

Nikolic, Milan, and Sinisa Djordjevic. "Alkaloids in the pharmaceutical industry: Structure, isolation and application." Chemical Industry 57, no. 10 (2003): 471–78. http://dx.doi.org/10.2298/hemind0310471n.

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By the end of the 18th and the beginning of the 19th century a new era began in medicine, pharmaceutics and chemistry that was strongly connected with alkaloids and alkaloid drugs. Even before that it was known that certain drugs administered in limited doses were medicines, and toxic if taken in larger doses (opium, coke leaves, belladonna roots, monkshood tubers crocus or hemlock seeds). However, the identification, isolation and structural characterization of the active ingredients of the alkaloid drugs was only possible in the mid 20th century by the use of modern extraction equipment and

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13

Chiba, Shunsuke, and Atsushi Kaga. "Synthesis of Tricyclic Marine Alkaloids, Cylindricines, Lepadiformines, Fasicularin, and Polycitorols: A Recent Update." Synthesis 50, no. 04 (2017): 685–99. http://dx.doi.org/10.1055/s-0036-1589521.

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Cylindricines, lepadiformines, and fasicularin are tricyclic marine alkaloids bearing perhydropyrrolo- and pyrido[2,1-j] frameworks having divergent chemical functionalities. They have been isolated from marine tunicates over the last two decades and found to have a range of cytotoxicity such as DNA-alkylating ability. Recently, polycitorols have emerged as a new member of this alkaloid family. Their unique structural features and biological activities have intrigued many researchers and challenged them in their synthesis. This review describes recent syntheses of the tricyclic alkaloids based

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14

Hájíček, Josef. "A Review on Recent Developments in Syntheses of the Post-Secodine Indole Alkaloids. Part I: The Primary Alkaloid Types." Collection of Czechoslovak Chemical Communications 69, no. 9 (2004): 1681–767. http://dx.doi.org/10.1135/cccc20041681.

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This first part of a planned review on developments in the field of total and formal total synthesis of the post-secodine indole alkaloids concentrates on primary alkaloid types. It reviews the synthesis of secodine, aspidospermane, pseudoaspidospermane and ibogane alkaloids; andranginine is also included. It covers the literature from 1992-1993 up to approximately May 2004. A review with 179 references.

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15

Jiao, Lei, Ze-Xin Zhang, and Si-Cong Chen. "Asymmetric Total Synthesis of (+)-Minfiensine by an Asymmetric Cascade Cyclization Strategy." Synlett 28, no. 17 (2017): 2199–204. http://dx.doi.org/10.1055/s-0036-1589075.

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The Strychnos alkaloid minfiensine and a series of akuammiline alkaloids, such as vincorine, aspidophylline A, and picrinine, possess a common core skeleton, a 4a,9a-heterocycle-fused tetrahydrocarbazole. Efficient construction of this core structure in a highly enantioselective manner would facilitate the total synthesis of these alkaloids. In this article, we briefly summarize the established strategies for obtaining this core structure, together with the corresponding total-synthesis routes, and we describe our own effort on the development of a new strategy, the asymmetric cascade dearomat

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16

Zhang, Ye, Lei Zhang, and Xiangbing Qi. "Total Synthesis of (–)-Alstofolinine A: Selected Furan Oxidation/ Cyclization Cascade." Synlett 31, no. 01 (2019): 7–12. http://dx.doi.org/10.1055/s-0039-1690247.

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Indole-fused tetracyclic ring systems containing nitrogen atoms are common core skeletons of many indole alkaloids such as sarpagine, macroline, and ajmaline. Efficient and stereoselective construction of these ring systems can promote the development of the corresponding alkaloid syntheses. In this article, we briefly summarize our current progress toward the application of the aza-Achmatowicz reaction and indole nucleophilic addition reaction cascade for the first asymmetric total synthesis of the macroline-type indole alkaloid (–)-Alstofolinine A. Our synthetic strategy is based on furan ox

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17

Sha, C. K., S. J. Huang, C. M. Huang, A. W. Hong, and T. H. Jeng. "Anionic cyclization approach toward perhydroindoles. Total synthesis of montanine-type Amaryllidaceae alkaloids." Pure and Applied Chemistry 72, no. 9 (2000): 1773–76. http://dx.doi.org/10.1351/pac200072091773.

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Hexahydro-1H-indol-3-one can be used as a building block for alkaloid synthesis. Radical and anionic cyclization approaches toward this useful structure were developed. Approaches toward total synthesis of montanine-type Amaryllidaceae alkaloids using hexahydro-1H-indol-3-one as a key intermediate were studied.

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18

Hájíček, Josef. "A Review on Recent Developments in Syntheses of the post-Secodine Indole Alkaloids. Part II: Modified Alkaloid Types." Collection of Czechoslovak Chemical Communications 72, no. 7 (2007): 821–98. http://dx.doi.org/10.1135/cccc20070821.

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The second part of the planned review on developments in the field of total and formal total synthesis of the post-secodine indole alkaloids concentrates on modified alkaloid types, i.e. those skeletons derived from primary types by formation of additional and/or rupture of existing bonds, while connectivities next to indol(e)ine moiety remain intact. It thus reviews the synthesis of alkaloids of quebrachamine/cleavamine type including VLB-bis-indoles, rhazinilam type, aspidofractinine/kopsane and kopsifoline type, as well as kopsijasminilam alkaloids, lapidilectine B and danuphylline. It cove

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19

Bhambhani, Sweta, Kirtikumar R. Kondhare, and Ashok P. Giri. "Diversity in Chemical Structures and Biological Properties of Plant Alkaloids." Molecules 26, no. 11 (2021): 3374. http://dx.doi.org/10.3390/molecules26113374.

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Phytochemicals belonging to the group of alkaloids are signature specialized metabolites endowed with countless biological activities. Plants are armored with these naturally produced nitrogenous compounds to combat numerous challenging environmental stress conditions. Traditional and modern healthcare systems have harnessed the potential of these organic compounds for the treatment of many ailments. Various chemical entities (functional groups) attached to the central moiety are responsible for their diverse range of biological properties. The development of the characterization of these plan

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20

Shi, Yingbo, Haibing He, and Shuanhu Gao. "Recent advances in the total synthesis of gracilamine." Chemical Communications 54, no. 92 (2018): 12905–13. http://dx.doi.org/10.1039/c8cc07799a.

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Gracilamine belongs to the Amaryllidaceae alkaloid group and has a unique five-ring skeleton. This review will summarize the synthetic studies of gracilamine, and hopes to bring new inspiration to the research of Amaryllidaceae alkaloids.

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21

Thavaneswaran, Shanti, Kristy McCamley, and Peter J. Scammells. "N-Demethylation of Alkaloids." Natural Product Communications 1, no. 10 (2006): 1934578X0600101. http://dx.doi.org/10.1177/1934578x0600101008.

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The removal of an N-methyl group, or N-demethylation, is a useful chemical transformation in organic synthesis which has particular importance in the field of alkaloid chemistry. Historically, tertiary N-methyl alkaloids have been N-demethylated using the same methods as for N-dealkylating tertiary amines. Such methodologies have included the von Braun reaction, the use of chloroformate and azodicarboxylate reagents and the Polonovski reaction, amongst others. Photochemical and biochemical procedures have also been successfully employed. This review will examine these N-demethylation procedure

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22

Bhattacharyya, Dipanjan. "The galbulimima alkaloids—a new frontier in alkaloid synthesis." Tetrahedron 67, no. 31 (2011): 5525–42. http://dx.doi.org/10.1016/j.tet.2011.04.074.

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23

Supriyono, A., B. Schwarz, V. Wray, et al. "Bioactive Alkaloids from the Tropical Marine Sponge Axinella carteri." Zeitschrift für Naturforschung C 50, no. 9-10 (1995): 669–74. http://dx.doi.org/10.1515/znc-1995-9-1012.

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Abstract Analysis of the tropical marine sponge Axinella carteri afforded six unusual alkaloids, including the new brominated guanidine derivative 3-bromo-hymenialdisine. The structure elucidation of the new alkaloid is described. The alkaloid patterns of sponges collected in Indonesia or in the Philippines were shown to be qualitatively identical suggesting de novo synthesis by the sponge or by endosymbiontic microorganisms rather than uptake by filterfeeding. All alkaloids were screened for insecticidal activity as well as for cytotoxicity. The guanidine alkaloids hymenialdisine and debromoh

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24

Chattopadhyay, Amit Kumar, and Stephen Hanessian. "Cyclic enaminones. Part II: applications as versatile intermediates in alkaloid synthesis." Chemical Communications 51, no. 92 (2015): 16450–67. http://dx.doi.org/10.1039/c5cc05892a.

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Among many other strategies, the enaminone approach is an important strategy to construct and diversify the azacyclic core in various alkaloids syntheses. In this brief review we discuss the application of cyclic enaminones as building blocks, as well as potential intermediates in the total synthesis of selected alkaloids.

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25

Strunz, George M., and Heather J. Finlay. "Expedient synthesis of unsaturated amide alkaloids from Piper spp: Exploring the scope of recent methodology." Canadian Journal of Chemistry 74, no. 3 (1996): 419–32. http://dx.doi.org/10.1139/v96-046.

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The Sakai aryl aldehyde – cyclic ketone aldol – Grob fragmentation sequence was extended to cinnamaldehyde and cyclohexanone, and the product was elaborated to analogues of the alkaloid piperstachine. The effects of substituents on the reaction involving cinnamaldehyde were studied. The aldol-fragmentation sequence failed with benzaldehyde when cyclooctanone or cyclobutanone was substituted for cyclohexanone or cyclopentanone, and the reasons for this failure were examined. Four-carbon Wittig homologation of the piperonal–cyclobutanone aldol-fragmentation product, a hypothetical route to alkal

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26

Burtoloso, Antonio, Ariane Bertonha, and Isac Rosset. "Synthesis of Alkaloids: Recent Advances in the Synthesis of Phenanthroindolizidine Alkaloids." Current Topics in Medicinal Chemistry 14, no. 2 (2013): 191–99. http://dx.doi.org/10.2174/1568026613666131213154633.

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27

Manna, Ranjan K., P. Jaisankar, and Venkatachalam S. Giri. "Synthesis of Indole Alkaloids and Alkaloidal Precursors: An Improved Synthesis of Flavopereirine." Journal of Chemical Research 23, no. 6 (1999): 350–51. http://dx.doi.org/10.1177/174751989902300603.

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Synthesis of flavopereirine 1, formal synthesis of isogeissoschizines 8 and dihydrocorynantheols 9 through the intermediacy of 3-(2-hydroxyethyl)-6,7-dihydroindolo[2,3-a]quinolizine 3 and also the unexpected formation of the β-carbolines 12 and 13 on Huang-Minion reaction of 2 are described.

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28

Lima, Dimas J. P., Antonio E. G. Santana, Michael A. Birkett, and Ricardo S. Porto. "Recent progress in the synthesis of homotropane alkaloids adaline, euphococcinine and N-methyleuphococcinine." Beilstein Journal of Organic Chemistry 17 (January 5, 2021): 28–41. http://dx.doi.org/10.3762/bjoc.17.4.

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The 9-azabicyclo[3.3.1]nonane ring system is present in several insect- and plant-derived alkaloids. (−)-Adaline (1) and (+)-euphococcinine (2), found in secretions of Coccinelid beetles, and (+)-N-methyleuphococcinine (3), isolated from the Colorado blue spruce Picea pungens, are members of this alkaloid family. Their unique bicyclic system with a quaternary stereocenter, and the potent biological activity exerted by these homotropane alkaloids, make them attractive synthetic targets. This work aims briefly to review the chemical ecology of Adalia bipunctata and the recent methodologies to ob

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29

Liang, Yu-Yan, Shi-Chao Lu, Ya-Ling Gong, and Shu Xu. "Strategies and Efforts towards the Total Synthesis of Palhinine Alkaloids." Molecules 25, no. 18 (2020): 4211. http://dx.doi.org/10.3390/molecules25184211.

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The palhinine family of Lycopodium alkaloids were first reported in 2010, which feature an intriguing isotwistane carbon cage and a nine-membered azonane ring. It is noteworthy that the tetracyclic 5/6/6/9 skeleton was unprecedented in Lycopodium alkaloids before their seminal discovery. Over the past decade, extensive synthetic efforts stemming from seven research groups have resulted in two racemic total syntheses to date. This review article takes the opportunity to survey these efforts and achievements so as to promote further research towards the asymmetric total synthesis of palhinine al

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30

Berkov, Strahil, Atanas Pavlov, Vasil Georgiev, et al. "Alkaloid Synthesis and Accumulation in Leucojum Aestivum in Vitro Cultures." Natural Product Communications 4, no. 3 (2009): 1934578X0900400. http://dx.doi.org/10.1177/1934578x0900400328.

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The alkaloids of intact plants, calli and shoot-clump cultures of L. aestivum were analyzed by GC-MS. Twenty-four alkaloids were detected. Calli appeared to produce sparse alkaloid profiles in stark contrast to shoot-clumps that had similar profiles to those of the intact plant. Seven shoot-clump strains produced galanthamine predominantly whereas another three were dominated by lycorine. Shoot-clump strains cultivated under light accumulated about two-times more galanthamine (an average of 74 μg/g of dry weight) than those cultivated in darkness (an average of 39 μg/g of dry weight). In compa

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31

Kumar, Pradeep, та Brijesh Sharma. "Proline-Catalyzed Asymmetric α-Amination in the Synthesis of Bioactive Molecules". Synlett 29, № 15 (2018): 1944–56. http://dx.doi.org/10.1055/s-0037-1610022.

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The direct α-amination of carbonyl compounds using organocatalysts represents a powerful and atom-economical tool for asymmetric C–N bond formation. We describe a complete account of α-functionalization of carbonyl compounds, through iterative sequential α-aminoxylation/amination using electrophilic O and N sources, as well as sequential α-amination/HWE reaction for enantio- and diastereoselective synthesis of both syn- and anti-1,3-aminoalcohols and 1,3-diamines. Additionally this protocol is further extended for the easy construction of alkaloids such as indolizidine, pyrrolizidine, and quin

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32

P. Cava, Michael, and E. Kyle Stephenson. "Synthesis of Proaporphine Alkaloids." HETEROCYCLES 39, no. 2 (1994): 891. http://dx.doi.org/10.3987/rev-94-sr(b)3.

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33

Rozwadowska, Maria D., and Maria Chrzanowska. "Synthesis of secoisoquinoline alkaloids." Tetrahedron 42, no. 24 (1986): 6669–72. http://dx.doi.org/10.1016/s0040-4020(01)82106-2.

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34

Kobayashi, Yuichi, and Tsuyoshi Itoyama. "Synthesis of Cinchona Alkaloids." Journal of Synthetic Organic Chemistry, Japan 65, no. 6 (2007): 598–607. http://dx.doi.org/10.5059/yukigoseikyokaishi.65.598.

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35

Yokoshima, Satoshi. "Synthesis of Lycopodium Alkaloids." Journal of Synthetic Organic Chemistry, Japan 75, no. 10 (2017): 1035–44. http://dx.doi.org/10.5059/yukigoseikyokaishi.75.1035.

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36

Moody, Christopher J. "Synthesis of Carbazole Alkaloids." Synlett 1994, no. 09 (1994): 681–88. http://dx.doi.org/10.1055/s-1994-22975.

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37

Birman, Vladimir B., and Xun-Tian Jiang. "Synthesis of Sceptrin Alkaloids." Organic Letters 6, no. 14 (2004): 2369–71. http://dx.doi.org/10.1021/ol049283g.

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38

Bergman, J., and B. Pelcman. "Synthesis of carbazole alkaloids." Pure and Applied Chemistry 62, no. 10 (1990): 1967–76. http://dx.doi.org/10.1351/pac199062101967.

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39

Vinogradova, V. I., and M. S. Yunusov. "Synthesis of protoberberine alkaloids." Chemistry of Natural Compounds 28, no. 5 (1992): 391–407. http://dx.doi.org/10.1007/bf00630639.

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40

Manna, Ranjan K., P. Jaisankar, and Venkatachalam S. Giri. "Synthesis of Indole Alkaloids and Alkaloidal Precursors: an Improved Synthesis of Flavopereirine." Journal of Chemical Research, no. 6 (1999): 350–51. http://dx.doi.org/10.1039/a900979e.

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41

Ohno, Hiroaki, and Shinsuke Inuki. "Nonbiomimetic total synthesis of indole alkaloids using alkyne-based strategies." Organic & Biomolecular Chemistry 19, no. 16 (2021): 3551–68. http://dx.doi.org/10.1039/d0ob02577a.

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Significance of nonbiomimetic natural product synthesis and nonbiomimetic total syntheses of indole alkaloids based on the construction of core structures using alkyne reactions are summarized in this review.

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42

Keck, Gary E., Erik N. K. Cressman, and Eric J. Enholm. "Intramolecular allylstannane cyclizations in alkaloid synthesis: applications to pyrrolizidine alkaloids." Journal of Organic Chemistry 54, no. 18 (1989): 4345–49. http://dx.doi.org/10.1021/jo00279a022.

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43

Mayer, Szabolcs, András Keglevich, Csilla Sepsey Für, et al. "Results in Chemistry of Natural Organic Compounds. Synthesis of New Anticancer Vinca Alkaloids and Flavone Alkaloids." Chemistry 2, no. 3 (2020): 714–26. http://dx.doi.org/10.3390/chemistry2030046.

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The antitumor indole–indoline alkaloids of the evergreen Catharanthus roseus—namely vinblastine and vincristine—are widely used in chemotherapy of cancer. Many efforts were made to synthesize more efficient derivatives with less side-effect. The 14,15-cyclopropane derivative of vinblastine was synthesized successfully by a five-step procedure starting from vindoline. Vincristine, vinorelbine and several derivatives condensed with a cyclopropane ring were synthesized. Various hybrid molecules were prepared by the coupling reaction of vindoline and methyl ester of tryptophan, which were conjugat

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Tao, Hongyu, Ling Zuo, Huanli Xu, et al. "Alkaloids as Anticancer Agents: A Review of Chinese Patents in Recent 5 Years." Recent Patents on Anti-Cancer Drug Discovery 15, no. 1 (2020): 2–13. http://dx.doi.org/10.2174/1574892815666200131120618.

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Background: In recent years, many novel alkaloids with anticancer activity have been found in China, and some of them are promising for developing as anticancer agents. Objective: This review aims to provide a comprehensive overview of the information about alkaloid anticancer agents disclosed in Chinese patents, and discusses their potential to be developed as anticancer drugs used clinically. Methods: Anticancer alkaloids disclosed in Chinese patents in recent 5 years were presented according to their mode of actions. Their study results published on PubMed, and SciDirect databases were pres

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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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Ryan, Suzanne M., Kathleen D. DeBoer, and John D. Hamill. "Alkaloid production and capacity for methyljasmonate induction by hairy roots of two species in Tribe Anthocercideae, family Solanaceae." Functional Plant Biology 42, no. 8 (2015): 792. http://dx.doi.org/10.1071/fp15045.

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In addition to producing medicinally important tropane alkaloids, some species in the mainly Australian Solanaceous tribe Anthocercideae, sister to genus Nicotiana, are known to also contain substantial levels of the pyridine alkaloids nicotine and nornicotine. Here, we demonstrate that axenic hairy root cultures of two tribe Anthocercideae species, Cyphanthera tasmanica Miers and Anthocercis ilicifolia ssp. ilicifolia Hook, contain considerable amounts of both nicotine and nornicotine (~0.5–1% DW), together with lower levels of the tropane alkaloid hyoscyamine (<0.2% DW). Treatment of grow

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Zu, Liansuo, and Xiaoni Xie. "Skeletal Rearrangements as Strategies for the Total Syntheses of Indole Alkaloids." Synlett 29, no. 08 (2018): 1008–13. http://dx.doi.org/10.1055/s-0036-1591560.

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In this account, we summarize our recent efforts in the total syntheses of several indole alkaloids, including minfiensine, calophyline A, deformylcorymine, strictamine, and goniomitine. Our central theme is to utilize skeletal rearrangements as key strategies for generating complex structures.1 Introduction2 The Development of an Aza-Pinacol Rearrangement3 Applications of Aza-Pinacol Rearrangements in Total Syntheses4 Strategy Extension: The Total Synthesis of Goniomitine5 Conclusion

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Robertson, Jeremy, and Kiri Stevens. "Pyrrolizidine alkaloids." Nat. Prod. Rep. 31, no. 12 (2014): 1721–88. http://dx.doi.org/10.1039/c4np00055b.

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Yin, Yuling, Riko Katahira, and Hiroshi Ashihara. "Metabolism of Purine Alkaloids and Xanthine in Leaves of Maté (Ilex paraguariensis)." Natural Product Communications 10, no. 5 (2015): 1934578X1501000. http://dx.doi.org/10.1177/1934578x1501000503.

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Accumulation and metabolism of purine alkaloids in leaves of maté ( Ilex paraguariensis) were investigated. In winter, leaves accumulated caffeine but not theobromine, indicating that caffeine is the end product of purine alkaloid synthesis in maté. To elucidate the purine alkaloid metabolism in maté leaves, the metabolic fate of [8-14C]theobromine, [8-14C]theophylline, [8-14C]caffeine and [8-14C] xanthine was investigated in the leaf disks of young and mature leaves. In young maté leaves, significant amounts of theobromine and theophylline were utilized for caffeine biosynthesis, but the conv

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Wang, Dao Wu, Xiao Long Li, Xin Xia Feng, Jin Long Zheng, and Long Zhang. "Synthesis of Tetrahydropalmatine." Advanced Materials Research 850-851 (December 2013): 1193–96. http://dx.doi.org/10.4028/www.scientific.net/amr.850-851.1193.

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Tetrahydropalmatine in overall yield of 18% was synthesized from alkaloids in Coptids Rhizoma with the similar structure of isoquinoline by a three-step reaction of alkaloids preparation, demethylation or demethylene-dioxy, deoxidation, methylation and so on. The structure was confirmed by 1H-NMR IR and ESI-MS.

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