Journal articles on the topic 'Indolizidine'

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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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2

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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3

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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4

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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5

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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6

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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7

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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8

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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9

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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10

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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11

Michael, Joseph P. "Indolizidine and quinolizidine alkaloids." Natural Product Reports 19, no. 6 (October 8, 2002): 719–41. http://dx.doi.org/10.1039/b104969k.

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12

Grundon, M. F. "Indolizidine and quinolizidine alkaloids." Natural Product Reports 2, no. 3 (1985): 235. http://dx.doi.org/10.1039/np9850200235.

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13

Grundon, M. F. "Indolizidine and quinolizidine alkaloids." Natural Product Reports 4 (1987): 415. http://dx.doi.org/10.1039/np9870400415.

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14

Grundon, M. F. "Indolizidine and quinolizidine alkaloids." Natural Product Reports 6, no. 5 (1989): 523. http://dx.doi.org/10.1039/np9890600523.

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15

Michael, J. P. "Indolizidine and quinolizidine alkaloids." Natural Product Reports 7, no. 6 (1990): 485. http://dx.doi.org/10.1039/np9900700485.

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16

Michael, Joseph P. "Indolizidine and quinolizidine alkaloids." Natural Product Reports 17, no. 6 (2000): 579–602. http://dx.doi.org/10.1039/a904849i.

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17

Michael, J. P. "Indolizidine and quinolizidine alkaloids." Natural Product Reports 8, no. 6 (1991): 553. http://dx.doi.org/10.1039/np9910800553.

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18

Michael, J. P. "Indolizidine and quinolizidine alkaloids." Natural Product Reports 10, no. 1 (1993): 51. http://dx.doi.org/10.1039/np9931000051.

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19

Michael, J. P. "Indolizidine and quinolizidine alkaloids." Natural Product Reports 11 (1994): 17. http://dx.doi.org/10.1039/np9941100017.

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20

Michael, J. P. "Indolizidine and quinolizidine alkaloids." Natural Product Reports 11, no. 6 (1994): 639. http://dx.doi.org/10.1039/np9941100639.

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21

Michael, J. P. "Indolizidine and quinolizidine alkaloids." Natural Product Reports 12, no. 5 (1995): 535. http://dx.doi.org/10.1039/np9951200535.

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22

Michael, Joseph P. "Indolizidine and quinolizidine alkaloids." Natural Product Reports 14, no. 1 (1997): 21. http://dx.doi.org/10.1039/np9971400021.

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23

Michael, Joseph P. "Indolizidine and quinolizidine alkaloids." Natural Product Reports 14, no. 6 (1997): 619. http://dx.doi.org/10.1039/np9971400619.

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24

Boulaajaj, Saïd, Thierryp Le Gall, Michel Vaultier, René Grée, Loïc Toupet, and Robert Carrié. "A new indolizidine synthesis." Tetrahedron Letters 28, no. 16 (January 1987): 1761–64. http://dx.doi.org/10.1016/s0040-4039(00)95414-5.

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25

Michael, Joseph P. "Indolizidine and quinolizidine alkaloids." Natural Product Reports 21, no. 5 (2004): 625. http://dx.doi.org/10.1039/b310689f.

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26

Michael, Joseph P. "Indolizidine and quinolizidine alkaloids." Natural Product Reports 16, no. 6 (1999): 675–96. http://dx.doi.org/10.1039/a809404g.

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27

P. Michael, Joseph. "Indolizidine and quinolizidine alkaloids." Natural Product Reports 15, no. 6 (1998): 571. http://dx.doi.org/10.1039/a815571y.

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28

Michael, Joseph P. "Indolizidine and quinolizidine alkaloids." Nat. Prod. Rep. 25, no. 1 (2008): 139–65. http://dx.doi.org/10.1039/b612166g.

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29

Michael, Joseph P. "Indolizidine and quinolizidine alkaloids." Natural Product Reports 22, no. 5 (2005): 603. http://dx.doi.org/10.1039/b413748p.

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30

Dai, Guang Zhi, Wen Bo Han, Ya Ning Mei, Kuang Xu, Rui Hua Jiao, Hui Ming Ge, and Ren Xiang Tan. "Pyridoxal-5′-phosphate–dependent bifunctional enzyme catalyzed biosynthesis of indolizidine alkaloids in fungi." Proceedings of the National Academy of Sciences 117, no. 2 (December 27, 2019): 1174–80. http://dx.doi.org/10.1073/pnas.1914777117.

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Indolizidine alkaloids such as anticancer drugs vinblastine and vincristine are exceptionally attractive due to their widespread occurrence, prominent bioactivity, complex structure, and sophisticated involvement in the chemical defense for the producing organisms. However, the versatility of the indolizidine alkaloid biosynthesis remains incompletely addressed since the knowledge about such biosynthetic machineries is only limited to several representatives. Herein, we describe the biosynthetic gene cluster (BGC) for the biosynthesis of curvulamine, a skeletally unprecedented antibacterial indolizidine alkaloid from Curvularia sp. IFB-Z10. The molecular architecture of curvulamine results from the functional collaboration of a highly reducing polyketide synthase (CuaA), a pyridoxal-5′-phosphate (PLP)-dependent aminotransferase (CuaB), an NADPH-dependent dehydrogenase (CuaC), and a FAD-dependent monooxygenase (CuaD), with its transportation and abundance regulated by a major facilitator superfamily permease (CuaE) and a Zn(II)Cys6 transcription factor (CuaF), respectively. In contrast to expectations, CuaB is bifunctional and capable of catalyzing the Claisen condensation to form a new C–C bond and the α-hydroxylation of the alanine moiety in exposure to dioxygen. Inspired and guided by the distinct function of CuaB, our genome mining effort discovers bipolamines A−I (bipolamine G is more antibacterial than curvulamine), which represent a collection of previously undescribed polyketide alkaloids from a silent BGC in Bipolaris maydis ATCC48331. The work provides insight into nature’s arsenal for the indolizidine-coined skeletal formation and adds evidence in support of the functional versatility of PLP-dependent enzymes in fungi.
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31

Klochkov, Sergey, and Margarita Neganova. "Unique indolizidine alkaloid securinine is a promising scaffold for the development of neuroprotective and antitumor drugs." RSC Advances 11, no. 31 (2021): 19185–95. http://dx.doi.org/10.1039/d1ra02558a.

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32

Harris, Joel M., and Albert Padwa. "A Flexible Approach toward Trisubstituted Piperidines and Indolizidines: Synthesis of 6-epi-Indolizidine 223A." Journal of Organic Chemistry 68, no. 11 (May 2003): 4371–81. http://dx.doi.org/10.1021/jo034324s.

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33

Preindl, Johannes, Shyamal Chakrabarty, and Jérôme Waser. "Dearomatization of electron poor six-membered N-heterocycles through [3 + 2] annulation with aminocyclopropanes." Chemical Science 8, no. 10 (2017): 7112–18. http://dx.doi.org/10.1039/c7sc03197a.

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34

Huang, Pei-Qiang, Ying-Hong Huang, and Shu-Ren Wang. "One-pot synthesis of N-heterocycles and enimino carbocycles by tandem dehydrative coupling–reductive cyclization of halo-sec-amides and dehydrative cyclization of olefinic sec-amides." Organic Chemistry Frontiers 4, no. 3 (2017): 431–44. http://dx.doi.org/10.1039/c6qo00720a.

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35

HOLMES, A. B., A. L. SMITH, S. F. WILLIAMS, L. R. HUGHES, Z. LIDERT, and C. SWITHENBANK. "ChemInform Abstract: Stereoselective Synthesis of (.+-.)-Indolizidines 167B, 205A, and 207A. Enantioselective Synthesis of (-)-Indolizidine 209B." ChemInform 22, no. 28 (August 23, 2010): no. http://dx.doi.org/10.1002/chin.199128227.

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36

Chalard, Pierre, Roland Remuson, Yvonne Gelas-Mialhe, Jean-Claude Gramain, and Isabelle Canet. "Enantioselective synthesis of (−)-indolizidine 167B." Tetrahedron Letters 40, no. 9 (February 1999): 1661–64. http://dx.doi.org/10.1016/s0040-4039(99)00059-3.

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37

Liou, Bo-Sian, Ruei-Fong Jhang, and Shang-Shing P. Chou. "Formal synthesis of (±)-indolizidine 209B." Tetrahedron 70, no. 41 (October 2014): 7458–63. http://dx.doi.org/10.1016/j.tet.2014.08.015.

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38

Machinaga, Nobuo, and Chihiro Kibayashi. "Total synthesis of (–)-indolizidine 239CD." J. Chem. Soc., Chem. Commun., no. 6 (1991): 405–7. http://dx.doi.org/10.1039/c39910000405.

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39

Fellah, Mouloud, Gérard Lhommet, and Virginie Mouriès-Mansuy. "Total Synthesis of Indolizidine (+)-223A." European Journal of Organic Chemistry 2012, no. 3 (December 7, 2011): 463–65. http://dx.doi.org/10.1002/ejoc.201101530.

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40

Angle, Steven R., and Robert M. Henry. "Synthesis of Enantiopure Indolizidine Alkaloids from α-Amino Acids: Total Synthesis of (−)-Indolizidine 167B." Journal of Organic Chemistry 62, no. 24 (November 1997): 8549–52. http://dx.doi.org/10.1021/jo970591k.

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41

Song, Yongcheng, Sentaro Okamoto, and Fumie Sato. "A concise asymmetric synthesis of 5,8-disubstituted indolizidine alkaloids. Total synthesis of (−)-indolizidine 209B." Tetrahedron Letters 43, no. 48 (November 2002): 8635–37. http://dx.doi.org/10.1016/s0040-4039(02)02149-4.

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42

Enders, Dieter, and Christoph Thiebes. "Efficient stereoselective syntheses of piperidine, pyrrolidine, and indolizidine alkaloids." Pure and Applied Chemistry 73, no. 3 (January 1, 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 frogs. The a-alkylation of aldehyde-SAMP/RAMP hydrazones has been used in the enantioselective synthesis of two epimers of stenusine, a 3-substituted piperidine alkaloid and spreading reagent of the beetle Stenus comma.
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43

Conforti, Irene, and Alberto Marra. "Iminosugars as glycosyltransferase inhibitors." Organic & Biomolecular Chemistry 19, no. 25 (2021): 5439–75. http://dx.doi.org/10.1039/d1ob00382h.

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The review describes the syntheses and inhibition properties of pyrrolidine, piperidine, azepane, pyrrolizidine and indolizidine iminosugars, as well as iminosugar nucleotides and iminodi- and -oligosaccharides.
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44

Saikia, Anil K., Kiran Indukuri, and Jagadish Das. "Stereoselective synthesis of O-tosyl azabicyclic derivatives via aza Prins reaction of endocyclic N-acyliminium ions: application to the total synthesis of (±)-epi-indolizidine 167B and 209D." Org. Biomol. Chem. 12, no. 36 (2014): 7026–35. http://dx.doi.org/10.1039/c4ob01130a.

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A diastereoselective synthesis of 4-O-tosyl piperidine containing azabicyclic derivatives has been established via Prins cyclization reaction. This protocol has been applied for the total synthesis of (±)-epi-indolizidine 167B and 209D.
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45

Chênevert, Robert, Ghodsi Mohammadi Ziarani, and Mohammed Dasser. "Chemoenzymatic Enantioselective Synthesis of (-)-Indolizidine 167B." HETEROCYCLES 51, no. 3 (1999): 593. http://dx.doi.org/10.3987/com-98-8421.

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46

Takahata, Hiroki, Hiroki Takahata, Hiroshi Bandoh, and Takefumi Momose. "An Asymmetric Synthesis of (+)-Indolizidine 195B." HETEROCYCLES 36, no. 12 (1993): 2777. http://dx.doi.org/10.3987/com-93-6511.

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47

Bloch, Robert, C残ile Brillet-Fernandez, Petra K殄n, and G屍ard Mandville. "An Enantioselective Synthesis of (+)-Indolizidine 195B." HETEROCYCLES 38, no. 7 (1994): 1589. http://dx.doi.org/10.3987/com-94-6723.

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48

R. Govindachari, Tuticorin, Sundaramoorthi Rajeswari, and Sundaram Chandrasekharan. "Syntheses of Indolizidine Alkaloids — A Review." HETEROCYCLES 25, no. 1 (1987): 659. http://dx.doi.org/10.3987/s-1987-01-0659.

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49

Leeper, Finian J., Padma Padmanabhan, Gordon W. Kirby, and Gary N. Sheldrake. "Biosynthesis of the indolizidine alkaloid, cyclizidine." Journal of the Chemical Society, Chemical Communications, no. 7 (1987): 505. http://dx.doi.org/10.1039/c39870000505.

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50

Corvo, Marta C., and M. Manuela A. Pereira. "A radical approach towards indolizidine 167B." Tetrahedron Letters 43, no. 3 (January 2002): 455–58. http://dx.doi.org/10.1016/s0040-4039(01)02189-x.

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