Relevant bibliographies by topics / Biomimetic total synthesis of Gracilamine

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  1. Journal articles
  2. Dissertations / Theses
  3. Books
  4. Book chapters
  5. Conference papers

Academic literature on the topic 'Biomimetic total synthesis of Gracilamine'

Author: Grafiati
Published: 11 December 2022
Last updated: 25 January 2023

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Journal articles on the topic "Biomimetic total synthesis of Gracilamine"

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Gao, Nadia (Yuqian), Martin G. Banwell, and Anthony C. Willis. "Biomimetic Total Synthesis of the PentacyclicAmaryllidaceaeAlkaloid Derivative Gracilamine." Organic Letters 19, no. 1 (2016): 162–65. http://dx.doi.org/10.1021/acs.orglett.6b03465.

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Tian, Songchuan, Weiwei Zi, and Dawei Ma. "Potentially Biomimetic Total Synthesis and Relative Stereochemical Assignment of (±)-Gracilamine." Angewandte Chemie International Edition 51, no. 40 (2012): 10141–44. http://dx.doi.org/10.1002/anie.201205711.

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Tian, Songchuan, Weiwei Zi, and Dawei Ma. "Potentially Biomimetic Total Synthesis and Relative Stereochemical Assignment of (±)-Gracilamine." Angewandte Chemie 124, no. 40 (2012): 10288–91. http://dx.doi.org/10.1002/ange.201205711.

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Shi, Yingbo, Baochao Yang, Shujun Cai, and Shuanhu Gao. "Total Synthesis of Gracilamine." Angewandte Chemie 126, no. 36 (2014): 9693–97. http://dx.doi.org/10.1002/ange.201405418.

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Shi, Yingbo, Baochao Yang, Shujun Cai, and Shuanhu Gao. "Total Synthesis of Gracilamine." Angewandte Chemie International Edition 53, no. 36 (2014): 9539–43. http://dx.doi.org/10.1002/anie.201405418.

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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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Shi, Yingbo, Baochao Yang, Shujun Cai, and Shuanhu Gao. "ChemInform Abstract: Total Synthesis of Gracilamine." ChemInform 46, no. 9 (2015): no. http://dx.doi.org/10.1002/chin.201509281.

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Chandra, Atish, Prachi Verma, Animesh Negel, and Ganesh Pandey. "Asymmetric Total Synthesis of (-)-Gracilamine Using a Bioinspired Approach." European Journal of Organic Chemistry 2017, no. 45 (2017): 6788–92. http://dx.doi.org/10.1002/ejoc.201701474.

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Zuo, Xiao-Dong, Shu-Min Guo, Rui Yang, Jian-Hua Xie, and Qi-Lin Zhou. "Asymmetric Total Synthesis of Gracilamine and Determination of Its Absolute Configuration." Organic Letters 19, no. 19 (2017): 5240–43. http://dx.doi.org/10.1021/acs.orglett.7b02517.

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Koser, Lilla, Vivian Miles Lechner, and Thorsten Bach. "Biomimetic Total Synthesis of Enterocin." Angewandte Chemie International Edition 60, no. 37 (2021): 20269–73. http://dx.doi.org/10.1002/anie.202108157.

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Dissertations / Theses on the topic "Biomimetic total synthesis of Gracilamine"

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Paddock, Victoria L. "A biomimetic total synthesis of clivonine." Thesis, Imperial College London, 2011. http://hdl.handle.net/10044/1/6400.

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The first chapter of this thesis discusses the biomimetic total synthesis of clivonine. Clivonine is a member of the Amaryllidaceae family of alkaloids and was isolated from the plant Clivia miniata Regel by Wildman in 1956. Barton first proposed the biosynthesis of the Amaryllidaceae alkaloids in 1958, hypothesising that the key diversifying step in the biosynthesis was an intramolecular phenolic oxidative coupling of a common precursor, norbelladine. However, it was not until 2 years later, in 1960, that Barton was able to account for the biosynthesis of the lycorenine class of the Amaryllid
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Meier, Robin [Verfasser], and Dirk [Akademischer Betreuer] Trauner. "Marine natural products from Aplysia dactylomela and Streptomyces spectabilis : Biomimetic and non-biomimetic total synthesis of aplydactone and Biomimetic total synthesis of merochlorin B / Robin Meier ; Betreuer: Dirk Trauner." München : Universitätsbibliothek der Ludwig-Maximilians-Universität, 2017. http://d-nb.info/1127527959/34.

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Pye, Richard Joseph. "The first total synthesis of mycaperoxide B : a biomimetic approach." Thesis, University of Reading, 2002. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.408986.

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De, Silvestro Irene. "Total synthesis of phenolic natural products." Thesis, University of Edinburgh, 2017. http://hdl.handle.net/1842/29575.

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This thesis is regarded with the biomimetic total synthesis of phenolic natural products and describes two different projects. Chapter 1 introduces phenolic natural products, the most important biosynthetic pathways for their formation and some examples of relevant biomimetic syntheses. A short introduction to dimeric and pseudo-dimeric natural products can also be found in this chapter. Specific introductions can be found at the start of Chapters 2 and 3. Chapter 2 describes the total synthesis of a dimeric thymol derivative isolated from Arnica sachalinensis (which we have named “thymarnicol
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Brown, Patrick Dylan. "Total synthesis of millingtonine and incargranines A and B." Thesis, University of Edinburgh, 2016. http://hdl.handle.net/1842/20983.

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Biomimetic synthesis is the branch of synthetic organic chemistry which attempts to learn from nature into order to solve the challenges of chemical synthesis. This thesis describes application of biomimetic principles to the total synthesis of three phenylethanoid alkaloid natural products: incargranine B; millingtonine and incargranine A. Chapter 1 provides a general introduction to the area. Specific introductions can be found at the start of each chapter. Chapter 1 introduces the concept of biomimicry and provides a brief overview of the development of the underlying concepts and terminolo
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Vala, Andrea. "Studies towards the total synthesis of penicillipyrone b via a biomimetic approach." Master's thesis, Alma Mater Studiorum - Università di Bologna, 2016. http://amslaurea.unibo.it/9882/.

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Pennicillipyrone A and B are two novel meroterpenoids isolated from the marine-derived fungus Penicilliump sp. Although a preliminary toxicity studies demonstrated the bioactivity of penicillipyrone A to be far superior to that of its congener penicillipyrone B, we were intrigued by its structure. Moreover, it appeared as though one could design an efficient total synthesis based on chemistry that was familiar to our laboratory. The purpose of this project was the study of a new synthesis of Pennicillipyrone B by way of a doubley-biomimetic approach. The intended approach proceeds through a p
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Cebon, Benjamin Isaiah Martin. "Studies towards the biomimetic total synthesis of dihydrooxepin-containing epipolythiodiketopiperazine natural products." Connect to thesis, 2009. http://repository.unimelb.edu.au/10187/8526.

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SCH-64874 (5) is a fungal metabolite that inhibits the epidermal growth factor receptor (EGFR), a high-profile oncology target, with an IC50 of 1.0µg/mL. It is of particular interest because it is unlikely to inhibit the protein’s intramolecular kinase domain (as typical chemical EGFR inhibitors do), and may act instead by obstructing the receptor’s ligand binding and/or dimerisation processes.<br>In this work, the epipolythiodiketopiperazine family of natural products is reviewed, leading to a discussion of the probable biosynthetic pathways by which these complex molecules are produced in na
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Natangelo, Anna. "Towards the first total synthesis of C-arylglucosidic ellagitannins : a biomimetic approach." Thesis, Bordeaux 1, 2010. http://www.theses.fr/2010BOR14019/document.

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Les ellagitannins C-arylglucosidiques sont des polyphenols naturels capable d’inhiber totalement la topoisomérase 2, une enzyme ciblée par les chimiothérapies utilisées contre le cancer. La challenge de cette these c’était trouver une approche biomimétique a la synthèse de ces molecules. La synthèse totale de la punicacorteine A, un simple membre de cette classe, a demande le développement de nouvelle méthodologies liée (i) à la chimie des sucres, pour la formation de la liaison C-arylglucosidique sur le glucose en forme ouverte et (ii) à la chimie des phénols pour générer l’unité biarylique e
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Anderson, Katie Elizabeth. "Biomimetic total synthesis of resorcylate natural products via a decarboxylative, allyl migration and aromatisation sequence." Thesis, Imperial College London, 2013. http://hdl.handle.net/10044/1/39340.

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Angelico in A (I), angelicoin B (II), cristatic acid (III) and grifolic acid (IV) (Figure A1) are members of the resorcylate family of natural products which contain a common 6-alkyl-2,4-dihydroxy benzoic acid core (β-resorcylate unit). The total syntheses of angelicoin A (I) and angelicoin B (II) from 2,2,6-trimethyl-4H-1,3-dioxin-4-one V are reported using late stage aromatisation reactions via diketo-dioxinones as advanced intermediates. In the case of angelicoin A (I), biomimetic aromatisation was coupled with a highly regioselective palladium(0)-catalysed decarboxylative prenyl migration
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Schmid, Matthias [Verfasser], and Thomas [Akademischer Betreuer] Magauer. "Biomimetic synthesis of complex flavonoids from East Indian Dragon's blood & total synthesis of salimabromide / Matthias Schmid ; Betreuer: Thomas Magauer." München : Universitätsbibliothek der Ludwig-Maximilians-Universität, 2019. http://d-nb.info/1191691993/34.

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Books on the topic "Biomimetic total synthesis of Gracilamine"

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service), SpringerLink (Online, ed. Total Synthesis of Plakortide E and Biomimetic Synthesis of Plakortone B. Springer Berlin Heidelberg, 2012.

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Sun, Xiao-Yu. Total Synthesis of Plakortide E and Biomimetic Synthesis of Plakortone B. Springer Berlin Heidelberg, 2012. http://dx.doi.org/10.1007/978-3-642-27195-3.

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Sun, Xiao-Yu. Total Synthesis of Plakortide E and Biomimetic Synthesis of Plakortone B. Springer, 2012.

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Total Synthesis Of Plakortide E And Biomimetic Synthesis Of Plakortone B. Springer, 2012.

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Sun, Xiao-Yu. Total Synthesis of Plakortide e and Biomimetic Synthesis of Plakortone B. Springer Berlin / Heidelberg, 2014.

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Book chapters on the topic "Biomimetic total synthesis of Gracilamine"

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Gaich, Tanja, and Johann Mulzer. "Biomimetic Total Synthesis of the Penifulvin Family." In Asymmetric Synthesis II. Wiley-VCH Verlag GmbH & Co. KGaA, 2013. http://dx.doi.org/10.1002/9783527652235.ch22.

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Brown, R. T. "Biomimetic and Total Synthesis of Monoterpenoid Isoquinoline Alkaloids." In Proceedings in Life Sciences. Springer Berlin Heidelberg, 1985. http://dx.doi.org/10.1007/978-3-642-70128-3_13.

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Sun, Xiao-Yu. "Introduction." In Total Synthesis of Plakortide E and Biomimetic Synthesis of Plakortone B. Springer Berlin Heidelberg, 2012. http://dx.doi.org/10.1007/978-3-642-27195-3_1.

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Sun, Xiao-Yu. "Results and Discussion." In Total Synthesis of Plakortide E and Biomimetic Synthesis of Plakortone B. Springer Berlin Heidelberg, 2012. http://dx.doi.org/10.1007/978-3-642-27195-3_2.

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Sun, Xiao-Yu. "Conclusion." In Total Synthesis of Plakortide E and Biomimetic Synthesis of Plakortone B. Springer Berlin Heidelberg, 2012. http://dx.doi.org/10.1007/978-3-642-27195-3_3.

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Sun, Xiao-Yu. "Experimental Section." In Total Synthesis of Plakortide E and Biomimetic Synthesis of Plakortone B. Springer Berlin Heidelberg, 2012. http://dx.doi.org/10.1007/978-3-642-27195-3_4.

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Lambert, Tristan H. "Total Synthesis of C–O Ring-Containing Natural Products." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0053.

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Scott A. Snyder at Columbia University demonstrated (J. Am. Chem. Soc. 2012, 134, 17714) that tetrahydrofuran 1 could be readily converted to oxocane 2 by treatment with the BDSB reagent developed in his laboratory. Reduction of 2 with DIBAL-H initiated a second ring closure by mesylate displacement to form the bicycle 3, which represented a formal total synthesis of laurefucin 4. Andrew L. Lawrence at the Australian National University found (Org. Lett. 2012, 14, 4537) that upon treatment with catalytic base, rengyolone 6, which was prepared in one pot from phenol 5, could be converted to the natural products incarviditone 7 and incarvilleatone 8. This demonstration provides strong support for the postulated biomimetic formation of these natural products. Shuanhu Gao at East China Normal University reported (Angew. Chem. Int. Ed. 2012, 51, 7786) the total synthesis of (+)-fusarisetin A 12 via biomimetic oxidation of equisetin 10 to produce the peroxy compound 11, followed by reduction. The bicyclic carbon skeleton of equisetin 10 was synthesized by intramolecular Diels-Alder reaction of trienyl aldehyde 9. The ellagitannin natural product (+)-davidiin 15 possesses a glucopyranose core with the unusual 1C4 (tetraaxial) conformation due to the presence of a biaryl bridge between two of the galloyl groups. Hidetoshi Yamada at Kwansei Gakuin University constructed (Angew. Chem. Int. Ed. 2012, 51, 8026) this bridge by oxidation with CuCl2 of 13, in which the three sterically demanding triisopropylsiloxy groups enforce the requisite tetraaxial conformation. John A. Porco, Jr. at Boston University applied (J. Am. Chem. Soc. 2012, 134, 13108) his asymmetric [3+2] photocycloaddition chemistry to the total synthesis of the aglain natural product (+)-ponapensin 20. Irradiation of hydroxyflavone 16 with methyl cinnamate 17 in the presence of diol 18 afforded the entire core framework 19 of ponapensin 20, which was accessed in just a few further synthetic transformations. Finally, Silas P. Cook at Indiana University reported (J. Am. Chem. Soc. 2012, 134,13577) a five-pot total synthesis of the antimalarial (+)-artemisinin 25. Cyclohexenone 21 was converted by simple operations to aldehyde 22. This aldehyde was then engaged in a [4+2] cycloaddition with the silyl ketene acetal 23 to produce, after an impressive Wacker oxidation of the disubstituted olefin, bicycle 24.
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Lambert, Tristan H. "Alkaloid Synthesis: Indolizidine 207A (Shenvi), (–)-Acetylaranotin (Reisman), Flinderole A (May), Isohaouamine B (Trauner), (–)-Strychnine (MacMillan)." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0059.

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Ryan A. Shenvi at the Scripps Research Institute in La Jolla has reported (J. Am. Chem. Soc. 2012, 134, 2012) a procedure for the stereoselective formal hydroamination of aminodienes to produce indolizidines. The procedure involves an amine-directed hydroboration, followed by a B to N bond migration (cf. 2) that is induced with molecular iodine and sodium methoxide. The pyrrolidinyl alcohols 3 generated upon oxidation can then be converted by a Mitsunobu reaction to the target bicyclic structures, including indolizidine 207A. Jeremy A. May at the University of Houston has shown (J. Am. Chem. Soc. 2012, 134, 6936) that a biomimetic strategy to access members of the flindersial alkaloids is viable. Borrerine can be prepared in two steps from tryptamine and subsequently dimerized by treatment with acid. Notably, the exclusive formation of either flinderoles A and C or isoborreverine can be achieved by treatment with either acetic acid or BF3•OEt2, respectively. The different outcomes of these dimerizations are the result of competing formal [3+2] and [4+2] cycloaddition pathways. The unusual paracyclophane-containing alkaloid haouamine B has undergone (J. Am. Chem. Soc. 2012, 134, 9291) a structural revision by Eva Zubia at the University of Cádiz due to the total synthesis of the reported structure (now called isohaouamine B) by Dirk Trauner at the University of Munich. To construct the strained paracyclophane moiety, the iodoamine 4 was deprotected and cyclized to produce structure 5. Aromatization of the cyclohexenone ring then provided the energetic offset for the strain present in 6. This route provided useful quantities of isohaouamine B for biological testing. Few natural products have captured the imaginations of chemists more than strychnine, and some of the most impressive achievements in the field of total synthesis have come from those who have taken up this challenge. David W.C. MacMillan at Princeton University has designed (Nature 2011, 475, 183) an enantioselective approach that not only furnishes (–)-strychnine in 12 steps, but also provides rapid access to a range of other biosynthetically related yet structurally diverse alkaloids, including (–)-akuammicine, (+)-aspidospermidine, (+)-vincadifformine, and (–)-kopsanone.
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Taber, Douglass F. "The Williams Synthesis of (–)-Khayasin." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0101.

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The tetranortriterpenoid (–)-khayasin 3 recently emerged as a potent and selective insecticide against the Coconut leaf beetle Brontispa longissima. In considering a synthetic route to 3, Craig M. Williams of the University of Queensland envisioned (J. Org. Chem. 2012, 77, 8913) the convergent preparation of the allyl vinyl ether 1 and subsequent Claisen rearrangement to the enone 2. To pursue this strategy, the ketone 8 and the allylic alcohol 15 had to be prepared in enantiomerically pure form. To this end, the DIP-Cl-derived enolate of the ketone 7 was added to the aldehyde 6 to give a secondary alcohol, exposure of which to KH led to the enone 8 in high ee. Methyl triflate converted the enone into the enol ether 9. The α-pinene used in the preparation of DIP-Cl was 83% ee. The authors have optimized (Adv. Synth. Catal. 2009, 351, 1148) the Morita-Baylis-Hillman addition of cyclohexenone 10 to formaldehyde to give, after silylation, the enone 11. Methylation followed by DIP-mediated aldol condensation with 13 led to the alcohol 14. Exposure of the derived acetate to lithium diisopropylamide induced cyclization and dehydration. Deprotection completed the preparation (Tetrahedron 2006, 62, 7355) of 15. Fortunately, the enantiomers of 15 could be separated chromatographically. Material having &gt;99% ee was taken onto the next step. Warming of 9 and 15 in the presence of acid delivered the coupled ketone 2 accompanied by the ether 1. Further heating of 1 converted it (Chem. Commun. 2011, 47, 2258) to 2. To form the last ring, the enone 2 was epoxidized to give 16. The reduction of 16 with aluminum amalgam gave preparatively useful amounts of 17. Esterification completed the synthesis of 3. Most total syntheses yield only the target natural product. In this biomimetic project, intermediates 15, 2, and 17 were themselves natural products, and oxidation of 17 delivered an additional natural product, 18. The preparation of 14 and of 8 underscores the importance of the asymmetric transformation of prochiral starting materials, cyclic and acyclic. Although DIP-Cl is used in stoichiometric amounts in both cases, it is not expensive. The preparation of 8, in particular, offers a potentially general approach to high ee-substituted cyclohexenones.
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Conference papers on the topic "Biomimetic total synthesis of Gracilamine"

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Gareis, Michael, and Jürgen Maas. "Acoustical Behaviour of Buckling Dielectric Elastomer Actuators." In ASME 2019 Conference on Smart Materials, Adaptive Structures and Intelligent Systems. American Society of Mechanical Engineers, 2019. http://dx.doi.org/10.1115/smasis2019-5747.

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Abstract Dielectric elastomers (DE) are regarded as a potential alternative to conventional actuator technologies. They feature low weight, high strains and low material costs. Their scope of application ranges from sensors, energy generators, smart textiles to biomimetic robots and much more. A few concepts of loudspeakers using DE have been demonstrated by the research community. One of the disadvantages of previously concepts was the need for mechanical bias (e.g. by air pressure). This work proposes a new concept of loudspeaker, which does not need prestretch or other means of mechanical b
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