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Relevant bibliographies by topics / Indole alkaloid synthesis

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Academic literature on the topic 'Indole alkaloid synthesis'

Author: Grafiati

Published: 4 June 2021

Last updated: 15 February 2022

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Journal articles on the topic "Indole alkaloid synthesis"

1

Zhang, Ye, Lei Zhang, and Xiangbing Qi. "Total Synthesis of (–)-Alstofolinine A: Selected Furan Oxidation/ Cyclization Cascade." Synlett 31, no. 01 (November 5, 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 oxidation/rearrangement and proceeds from easily accessible materials such as indole and furan derivatives.

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2

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 covers the literature of from 1991-1992 up to approximately end 2006. A review with 174 references.

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Gardette, Daniel, Jean-Claude Gramain, Marie-Eve Lepage, and Yves Troin. "Photocyclization of aryl enaminones. An efficient route to indole alkaloid synthons." Canadian Journal of Chemistry 67, no. 2 (February 1, 1989): 213–19. http://dx.doi.org/10.1139/v89-036.

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The photocyclization of enaminones was extended to aryl enaminones bearing a substituent on the aromatic moiety. This reaction was studied in order to achieve the synthesis of indole alkaloid synthons. Trials of regioselectivity control were made by using groups with enhanced steric hindrance. The reactivity of secondary enaminones was tested, and the ratio of C-alkylation to N-alkylation was shown to be dependent on the nature of the aromatic substituent. During this work, new hexahydrocarbazolones were synthesized, with substituents on the A ring or the modified C ring. Keywords: photocyclization, aryl enaminones, indole alkaloids, hexahydrocarbazolones-4, cyclopenta[b]indoles.

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4

Hájíček, Josef. "Recent developments in syntheses of the post-secodine indole alkaloids. Part III: Rearranged alkaloid types." Collection of Czechoslovak Chemical Communications 76, no. 12 (2011): 2023–83. http://dx.doi.org/10.1135/cccc2011099.

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The third part of a planned review on developments in the field of total and formal total synthesis of the post-secodine indole alkaloids focuses on types of rearranged alkaloids, i.e. on the skeletons with altered connectivities next to the indol(e)ine moiety, especially with a new bond to N-1. It reviews the synthesis of melodane, goniomitine, chippiine/dippinine, lirofoline and tronocarpine alkaloids, as well as alkaloids of secoschizozygane/vallesamidine, schizozygane and isoschizozygane type. It covers the literature from approximately 1991 up to May 2011. A review with 115 references.

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5

Okabe, Kazuaki, Hideaki Muratake, and Mitsutaka Natsume. "Total synthesis of indole alkaloid pendolmycin." Tetrahedron 46, no. 15 (January 1990): 5113–20. http://dx.doi.org/10.1016/s0040-4020(01)87818-2.

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6

Ortuno, J. C., and Y. Langlois. "Stereoselective synthesis of indole alkaloid cuanzine." Tetrahedron Letters 32, no. 35 (January 1991): 4491–94. http://dx.doi.org/10.1016/0040-4039(91)80020-7.

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7

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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8

Lounasmaa, Mauri, David Din Belle, and Arto Tolvanen. "Total synthesis of the indole alkaloid (±)-tacamonine." Tetrahedron Letters 36, no. 39 (September 1995): 7141–44. http://dx.doi.org/10.1016/0040-4039(95)01419-i.

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9

Magnus, Philip, Ian R. Matthews, James Schultz, Rudolf Waditschatka, and John C. Huffman. "Synthesis of the hexacyclic indole alkaloid (.+-.)-kopsijasmine." Journal of Organic Chemistry 53, no. 24 (November 1988): 5772–76. http://dx.doi.org/10.1021/jo00259a031.

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10

Zhu, Chenlong, Zhaobo Liu, Guanyu Chen, Kai Zhang, and Hanfeng Ding. "Total Synthesis of Indole Alkaloid Alsmaphorazine D." Angewandte Chemie 127, no. 3 (November 21, 2014): 893–96. http://dx.doi.org/10.1002/ange.201409827.

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Dissertations / Theses on the topic "Indole alkaloid synthesis"

1

Callaghan, Owen. "Synthetic and mechanistic studies in free radical." Thesis, University of Strathclyde, 1999. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.366957.

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2

Hollinshead, S. P. "Enantiospecific approaches to indole alkaloids." Thesis, University of York, 1987. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.379030.

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3

Ouali, Dehimi. "Enantioselective synthesis of novel corynanthe indole alkaloid synthons." Thesis, University of Salford, 1991. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.315329.

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4

Ferreira, Jasmin. "Asymmetric Total Synthesis of the Pentacyclic Indole Alkaloid (+)-Tacamonine." Master's thesis, Faculty of Science, 2019. http://hdl.handle.net/11427/31346.

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(+)-Tacamonine, a natural product isolated from the Central African plant Tabernaemontana eglandulosa, belongs to the relatively new tacaman class of pentacyclic monoterpenoid indole alkaloids. Its close structural similarity to the potent cerebral vasodilator (-)-vincamone has promoted several efforts towards its synthesis, culminating in the appearance of two asymmetric and seven racemic syntheses in the literature. This dissertation details the successful execution of our strategy for the concise, highly-efficient, asymmetric total synthesis of (+)-tacamonine. Chapter 1 serves as an introduction to the tacaman class, including the proposed biosynthesis for members of this class, followed by a review of the reported synthetic approaches to tacamonine. Chapter 2 details the evolution of our approach based on the use of key radical cyclization methodology to ultimately accomplish a total synthesis of the target. An investigation of the diastereoselectivity displayed in the radical cyclization step is also described through computational methods. Our route followed a novel ABC to ABCD to ABCDE ring-construction strategy, which first involved the synthesis of 3,4-dihydro--carboline as well as a chiral acid ester fragment that was acquired through Evans’ auxiliary-controlled alkylation chemistry. The latter set the absolute configuration at C-20 bearing the ethyl group in the D-ring, and thereafter, the two fragments were coupled together before being advanced to the radical cyclization precursor. Radical cyclization then led to the formation of the desired cis D/Ering junction in a diastereomeric ratio of 10:1, the major diastereomer displaying the required C-3/C-14 to C-20 anti-diastereoselectivity. Subsequent global reduction and oxidation/E-ring formation processes afforded the target in 8 steps over 10 operations in 25% overall yield and in 96% enantiomeric excess. X-Ray crystallographic structure determination provided conclusive evidence for the formation of the target.

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Barbey, Sabine. "A novel approach to the ergot alkaloid skeleton." Thesis, University of Reading, 1995. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.294855.

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6

Wingfield, M. "A novel approach to the total synthesis of corynanthe indole alkaloids via cyclopentanoid intermediaries." Thesis, University of Manchester, 1985. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.374789.

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7

Parker, Ashley Stuart. "Photochemical approaches to the synthesis of the indole alkaloid ibogamine." Thesis, University of Bristol, 2006. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.427907.

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8

Lebar, Matthew D. "Antarctic Tunicates and Endophytic Fungi: Chemical Investigation and Synthesis." Scholar Commons, 2010. http://scholarcommons.usf.edu/etd/3638.

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Drug discovery is reliant on new developments in natural product chemistry as well as advances in chemical synthesis. The interconnectivity and interdependence of natural and synthetic investigation in drug discovery is evident. The chemical exploration reported herein elaborates the relationship between natural product chemistry and chemical synthesis. Of particular interest are chemicals from organisms residing in less accessible environments, particularly Antarctica and endophytic microbial communities. Degradation via reductive ozonolysis of palmerolide A, a macrocyclic polyketide isolated from the Antarctic tunicate Synoicum adareanum, and subsequent synthetic preparation of the resulting polyols (1,2,6-hexanetriol and 1,2,3,6-hexanetetraol) led to a revision in the absolute configuration of the bioactive natural product (7R, 10R, 11R to 7S, 10S, 11S). A partial synthesis of palmerolide A (C3-14) was completed using Grubb’s 2nd generation catalyst to couple fragments formed using the previously developed methodology from the degradation study. Isolation of indole-pyrimidine containing alkaloids meridianins A, B, C, and E from the Antarctic tunicate Synoicum sp. prompted a synthetic investigation of psammopemmin A, a related alkaloid from the Antarctic sponge Psammopemma sp. resulting in reassignment of the structure of psammopemmin A to that of meridianin A. Both meridianin A and psammopemmin A were synthesized through a Suzuki coupling of the same 4-indolol nucleophile to the apposite pyrimidine electrophile. Several synthetic 3-pyrimidylindole analogs were also prepared and investigated for central nervous system, antimalarial, and cytotoxic activity. Chemical investigation of extracts from mangrove fungal endophytes that displayed antimalarial properties in vitro resulted in the isolation of several potent but cytotoxic and cytostatic compounds: cytochalasin D, roridin E, and 12,13-deoxyroridin E.

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9

Clauss, Rainer. "Radical cyclisation studies of chiral α-acylamino radicals : a model study towards Tacaman indole alkaloid synthesis." Master's thesis, University of Cape Town, 1996. http://hdl.handle.net/11427/16138.

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Includes bibliographical references.
he radical cyclisation of chiral 4,5-substituted N-acyl-2-aza-6-heptenyl radicals, derived from D-ribose, has been undertaken as a model stuay towards Tacaman indole alkaloid synthesis. The radical cyclisations were conducted using tributyltin hydride/AIBN in refluxing benzene. The α-acylamino radicals added to double bonds which were activated by an ethoxycarbonyl substituent. No reduction of the radicals by the tributyltin hydride was observed. Those radicals incorporating an isopropylidene ketal at the 4 and 5 positions as chiral auxiliary showed excellent regio- and stereoselectivity. Out of a possible 4 diastereomers, only two were obtained in a 2:8 ratio. It was established that the isopropylidene ketal directed the cyclisation stereoselectively and that no stereoselectivity was observed in the absence of the chiral auxiliary.

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10

Matsuoka, Junpei. "Total Synthesis of Indole Alkaloids Based on Direct Construction of Pyrrolocarbazaole Scaffolds via Gold-Catalyzed Cascade Cyclizations." Doctoral thesis, Kyoto University, 2020. http://hdl.handle.net/2433/253241.

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京都大学
0048
新制・課程博士
博士(薬学)
甲第22405号
薬博第843号
新制||薬||241(附属図書館)
京都大学大学院薬学研究科薬学専攻
(主査)教授大野浩章, 教授高須清誠, 教授竹本佳司
学位規則第4条第1項該当
Doctor of Pharmaceutical Sciences
Kyoto University
DFAM

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Books on the topic "Indole alkaloid synthesis"

1

Ouali, Dehimi. Enantioselective synthesis of novel Corynanthe indole alkaloid synthons. Salford: University of Salford, 1991.

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2

Matsuoka, Junpei. Total Synthesis of Indole Alkaloids. Singapore: Springer Singapore, 2020. http://dx.doi.org/10.1007/978-981-15-8652-1.

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3

Tirkkonen, Birgit. Stereoselective syntheses in the corynantheine series and of related model compounds. Helsinki: Suomalainen Tiedeakatemia, 1994.

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4

Callis, David John. Synthetic studies towards the indole alkaloid, aspidospermidine. 2001.

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5

Fray, Edward Brian. Synthetic approaches towards novel indole alkaloids. 1994.

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Book chapters on the topic "Indole alkaloid synthesis"

1

Lindel, Thomas, Nils Marsch, and Santosh Kumar Adla. "Indole Prenylation in Alkaloid Synthesis." In Topics in Current Chemistry, 67–129. Berlin, Heidelberg: Springer Berlin Heidelberg, 2011. http://dx.doi.org/10.1007/128_2011_204.

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2

Nakagawa, Masako, Toshiaki Nagata, Koji Ono, Hideharu Uchida, Takeshi Watanabe, Keisuke Hatakeyama, Masakatsu Akiba, Mihoko Fuwa, Mitsuhiro Arisawa, and Atsushi Nishida. "Recent Developments in Marine Indole Alkaloid Synthesis." In Advances in Experimental Medicine and Biology, 609–20. Boston, MA: Springer US, 2003. http://dx.doi.org/10.1007/978-1-4615-0135-0_70.

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3

Ninomiya, Ichiya. "Recent Progress in Our Indole Alkaloid Synthesis." In Natural Products Chemistry III, 187–213. Berlin, Heidelberg: Springer Berlin Heidelberg, 1988. http://dx.doi.org/10.1007/978-3-642-74017-6_10.

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4

Kutney, J. P. "The Synthesis of Indole Alkaloids." In Total Synthesis of Natural Products, 273–438. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2007. http://dx.doi.org/10.1002/9780470129661.ch2.

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5

Matsuoka, Junpei. "Introduction." In Total Synthesis of Indole Alkaloids, 1–18. Singapore: Springer Singapore, 2020. http://dx.doi.org/10.1007/978-981-15-8652-1_1.

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6

Matsuoka, Junpei. "Total Synthesis of Dictyodendrins by the Gold-Catalyzed Cascade Cyclization of Conjugated Diynes with Pyrroles." In Total Synthesis of Indole Alkaloids, 19–65. Singapore: Springer Singapore, 2020. http://dx.doi.org/10.1007/978-981-15-8652-1_2.

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7

Matsuoka, Junpei. "Construction of the Pyrrolo[2,3-d]Carbazole Core of Spiroindoline Alkaloids by Gold-Catalyzed Cascade Cyclization of Ynamide." In Total Synthesis of Indole Alkaloids, 67–79. Singapore: Springer Singapore, 2020. http://dx.doi.org/10.1007/978-981-15-8652-1_3.

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Matsuoka, Junpei. "Conclusion." In Total Synthesis of Indole Alkaloids, 81–82. Singapore: Springer Singapore, 2020. http://dx.doi.org/10.1007/978-981-15-8652-1_4.

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9

Arndt, Hans-Dieter, Lech-Gustav Milroy, and Stefano Rizzo. "Biomimetic Synthesis of Indole-Oxidized and Complex Peptide Alkaloids." In Biomimetic Organic Synthesis, 357–94. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2011. http://dx.doi.org/10.1002/9783527634606.ch10.

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Gaich, Tanja, and Johann Mulzer. "Biomimetic Synthesis of Alkaloids with a Modified Indole Nucleus." In Biomimetic Organic Synthesis, 149–80. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2011. http://dx.doi.org/10.1002/9783527634606.ch5.

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Conference papers on the topic "Indole alkaloid synthesis"

1

Wipf, Peter, and Filip Petronijevic. "New Approaches to Indoles and Indole Alkaloids." In 14th Brazilian Meeting on Organic Synthesis. São Paulo: Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-14bmos-r0388-1.

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Sousa, Emília, Solida Long, Diana Resende, Patrícia Pereira-Terra, Joana Freitas-Silva, Artur Silva, Maria Elizabeth Tiritan, et al. "Synthetic strategies towards bioactive nature-inspired indole-containing alkaloids." In 5th International Electronic Conference on Medicinal Chemistry. Basel, Switzerland: MDPI, 2019. http://dx.doi.org/10.3390/ecmc2019-06291.

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