Relevant bibliographies by topics / Total Synthesis, silicon

Contents

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

Academic literature on the topic 'Total Synthesis, silicon'

Author: Grafiati
Published: 6 September 2023

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Journal articles on the topic "Total Synthesis, silicon"

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Denmark, Scott E., and Shyh-Ming Yang. "Intramolecular Silicon-Assisted Cross-Coupling: Total Synthesis of (+)-Brasilenyne." Journal of the American Chemical Society 124, no. 51 (December 2002): 15196–97. http://dx.doi.org/10.1021/ja028936q.

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Li, Hongze, Hengmu Xie, Zhigao Zhang, Yongjin Xu, Ji Lu, Lu Gao, and Zhenlei Song. "Total synthesis of (−)-exiguolide via an organosilane-based strategy." Chemical Communications 51, no. 40 (2015): 8484–87. http://dx.doi.org/10.1039/c5cc02448j.

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An organosilane-based strategy has been used to accomplish the total synthesis of (–)-exiguolide. The key steps involve: (1) geminal bis(silyl) Prins cyclization to construct the A ring; (2) silicon-protected RCM reaction to construct the macrocycle; and (3) Hiyama–Denmark cross-coupling to install the side chain.
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Verma, Rekha, and Sunil K. Ghosh. "A silicon controlled total synthesis of the antifungal agent (+)-preussin." Chemical Communications, no. 17 (1997): 1601–2. http://dx.doi.org/10.1039/a703387g.

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Rodríguez-Escrich, Carles, Fèlix Urpí, and Jaume Vilarrasa. "Stereocontrolled Total Synthesis of Amphidinolide X via a Silicon-Tethered Metathesis Reaction." Organic Letters 10, no. 22 (November 20, 2008): 5191–94. http://dx.doi.org/10.1021/ol8021676.

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Denmark, Scott E, and Jack H C. Liu. "Silicon-Based Cross-Coupling Reactions in the Total Synthesis of Natural Products." Angewandte Chemie International Edition 49, no. 17 (March 23, 2010): 2978–86. http://dx.doi.org/10.1002/anie.200905657.

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Chowdhury, Partha Sarathi, and Pradeep Kumar. "Total Synthesis of Umuravumbolide and Hyptolide Through Silicon-Tethered Ring-Closing Metathesis." European Journal of Organic Chemistry 2013, no. 21 (June 12, 2013): 4586–93. http://dx.doi.org/10.1002/ejoc.201300302.

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VERMA, R., and S. K. GHOSH. "ChemInform Abstract: A Silicon Controlled Total Synthesis of the Antifungal Agent (+)-Preussin." ChemInform 29, no. 1 (June 24, 2010): no. http://dx.doi.org/10.1002/chin.199801235.

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Magnus, Philip, and Dominick Quagliato. "Silicon in synthesis. 21. Reagents for thiophenyl-functionalized cyclopentenone annulations and the total synthesis of (.+-.)-hirsutene." Journal of Organic Chemistry 50, no. 10 (May 1985): 1621–26. http://dx.doi.org/10.1021/jo00210a013.

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Denmark, Scott E., and Shyh-Ming Yang. "Total Synthesis of (+)-Brasilenyne. Application of an Intramolecular Silicon-Assisted Cross-Coupling Reaction." Journal of the American Chemical Society 126, no. 39 (October 2004): 12432–40. http://dx.doi.org/10.1021/ja0466863.

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Li, Fangzheng, and Marvin J. Miller. "Stereoselective Total Synthesis of (+)-Streptazolin by Using a Temporary Silicon-Tethered RCM Strategy." Journal of Organic Chemistry 71, no. 14 (July 2006): 5221–27. http://dx.doi.org/10.1021/jo060555y.

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Dissertations / Theses on the topic "Total Synthesis, silicon"

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Dumeunier, Raphaël. "New methodologies towards lactones and methylene-lactones : application to the total synthesis of Polycavernoside A." Université catholique de Louvain, 2004. http://edoc.bib.ucl.ac.be:81/ETD-db/collection/available/BelnUcetd-05242004-130732/.

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Methylene-butyrolactones are readily accessed by two methodologies based on a particular ene reaction. Both methodologies have been applied to the synthesis of the northern fragment of Polycavernoside. A reverse Julia reaction was used as the key step of a new methodology towards triene frameworks ; a mechanistic study revealed the unexpected role of triflic acid in the field of metal triflates catalysed acylation of alcohols, and a new tandem Brook rearrangement-allylation sequence was developed in the viewpoint of an improved total synthesis of Polycavernoside A.
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Whiting, Matthew Peter. "The silicon assisted Aza-[2,3] Wittig sigmatropic rearrangement : total synthesis of (+/-)-kainic acid and chirality transfer." Thesis, University of Nottingham, 2003. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.405386.

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Omollo, Ann Ondera. "TOTAL SYNTHESES OF (3S, 18S, 4E, 16E)-EICOSA-1,19-DIYNE-3,18-DIOL, (+)-DURYNE, (+)-DIDEOXYPETROSYNOL A, CICUTOXIN AND ATTEMPTS TOWARD THE TOTAL SYNTHESIS OF PETROSYNOL: POLYACETYLENIC POTENT ANTICANCER NATURAL PRODUCTS." Oxford, Ohio : Miami University, 2008. http://rave.ohiolink.edu/etdc/view?acc%5Fnum=miami1217877029.

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Lee, Jihoon. "Application of the silicon-directed annulation reactions to the total synthesis of natural products & studies directed toward the total synthesis of leiodolide A: preparation of the C13-C29 fragment." Thesis, 2013. https://hdl.handle.net/2144/14144.

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Brevisamide was isolated from the red tide dinoflagellate Karenia brevis in 2007. Key features of brevisamide include a substituted tetrahydropyran core and conjugated 3,4-dimethylhepta-2,4-dienal side chain. Total synthesis of brevisamide was highlighted by a stereoselective [4+2]-annulation of a (Z)-crotyl silane to furnish the substituted pyran core and Negishi cross-coupling to construct the conjugated dienal side chain. Successful application of the silane-based annulation methodology provided brevisamide in overall 17 steps and 6.4% overall yield from the known (Z)-crotyl silane. Isatisine A was isolated from the leaf and roots of Isatis indigotica in 2007. Total synthesis of isatisine A commenced with the development of a silyl-directed Mukaiyama-type [3+2]-annulation of an ethoxy allylsilane to construct a tetrahydrofuran core. [3+2]-Annulation reaction of an ethoxy allyl silane with 2-bromocinnamylaldehyde afforded the furan core as a single diastereomer. Further substrate-controlled indole addition and intramolecular copper(I)-mediated amidation provided (+)-isatisine A in overall 12 steps. One-pot Diels-Alder/annulation sequence was developed utilizing a silane-substituted 1,3-diene to give a fused-cyclic scaffold. In this reaction sequence, initial Lewis-acid-promoted Diels-Alder reaction between the silyl-substituted diene and a naphthoquinone constructed an intermediate cyclic allylsilane, and subsequent addition of aldehyde and Lewis acid triggered the annulation to construct a complex cyclic compound with high diastereoselectivity. This one-pot three component reaction sequence allowed for a simple access to various fused-polycyclic compounds, which bear a tetrahydropyran core. Leiodolide A was isolated from the deep-water marine sponge Leiodermatium. Leiodolide A was found to be significantly cytotoxic against HCT-116 human colon carcinoma with IC50 values = 1.4 ug/mL (2.5 uM). Since the natural product leiodolide A was found to comprise less than 0.001% of the dry weight of the sponge, establishing an efficient synthetic method to provide a significant amount of the natural product would be valuable to further biological studies. Our effort to synthesized upper fragment of leiodolide A was conducted through a series of cross-coupling reactions involving Stille coupling. Although proper conditions for the oxidation of (Z)-olefin to introduce the contiguous C15-17 triol system in leiodolide A were not achieved, this synthetic pathway would be useful in the total synthesis of leiodolide A.
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Procko, Kristen Jean. "Functionalization of C-aryl glycals and studies toward the total synthesis of 5-hydroxyaloin A." Thesis, 2009. http://hdl.handle.net/2152/28464.

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In the context of ongoing efforts toward C-aryl glycoside synthesis, a recently developed approach to form C-aryl glycals from 2-deoxysugar lactones was expanded to form novel substrates. This approach has been applied to the synthesis of various furyl glycals, allowing access to C-aryl glycals via a benzyne furan (4+2) cycloaddition methodology. The hydroboration-oxidation of said C-aryl glycals has allowed access to C(2)-oxygenated C-aryl glycosides via the benzyne cycloaddition approach. An approach to the total synthesis of 5-hydoxyaloin A is detailed, in which regioselective benzyne furan (4+2) cycloadditions were achieved via the use of a silicon tether. Two approaches to the anthrone core have been applied; one in which an unsymmetrically-substituted aryl ring is first constructed by means of a silicon tether, and one in which the unsymmetrically-substituted ring is formed last, also utilizing a silicon tether. The latter approach has allowed access to the anthrone core of 5-hydroxyaloin A, and only a final desulfurization remains in order to access the natural product.
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Book chapters on the topic "Total Synthesis, silicon"

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Denmark, Scott E., and Shyh-Ming Yang. "Chapter 4 Application of silicon-assisted intramolecular cross-coupling in total synthesis of (+)-brasilenyne." In Strategies and Tactics in Organic Synthesis, 100–136. Elsevier, 2005. http://dx.doi.org/10.1016/s1874-6004(05)80027-9.

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Taber, Douglass F. "Best Synthetic Methods: Reduction." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0008.

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Heshmatollah Alinezhad of Mazandaran University, Iran. developed (Tetrahedron Lett. 2009, 50, 659) the reagent 3, a white powder that is stable for many months, as a hydride donor for the reductive amination of aldehydes and ketones. Jean-Marc Campagne of the Institut Charles Gephardt Montpellier established (Synlett 2009, 276) a simple microwave protocol for reducing aldehydes and ketones to the corresponding hydrocarbons that looks general enough to become the method of choice for this important transformation. Joanne E. Harvey of Victoria University of Wellington, in the course of a total synthesis of Aigialomycind D, observed (J. Org. Chem. 2009, 74, 2271) that despite the high reactivity of the monosubstituted alkene of 7, the conjugated alkene could be selectively reduced. Brian S. Bodnar of SiGNa Chemistry described (J. Org. Chem. 2009, 74, 2598) a simple procedure for the reduction of an ester such as 9 to the alcohol 10, using Na dispersed on silica gel. Takao Ikariya of the Tokyo Institute of Technology designed (Angew. Chem. Int. Ed. 2009, 48, 1324) a Ru complex for the hydrogenation of N-acylsulfonamides and N-acylcarbamates such as 11 to the corresponding alcohol, 12. Remarkably, Hideo Nagashima of Kyushu University demonstrated (Chem. Commun. 2009, 1574) that even in the presence of the ester, the amide of 13 could be selectively reduced to the enamine 14. The enamine could be hydrolyzed to the aldehyde or reduced to the amine, but it is also an activated intermediate, for instance, for Michael addition to ethyl acrylate or methyl vinyl ketone. Diimide (HN=NH) is a useful reagent for selective reduction, as illustrated by the conversion of 15 to 17 . David R. Carbery of the University of Bath devised (J. Org. Chem. 2009, 74, 3186) a convenient procedure for the in situ generation of diimide from 16 and hydrazine hydrate. The reductive cleavage of tertiary nitriles to the corresponding hydrocarbon under dissolving metal conditions has been known for some time (J. Org. Chem. 1996, 61, 4219). Reduction of secondary nitriles required more forcing conditions, with K metal and crown ether (Tetrahedron Lett. 1985, 26, 6103).
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Taber, Douglass F. "Alkene and Alkyne Metathesis: (+)-Anamarine (Sabitha), ( ± )-Pseudotabersonine (Martin), Lactimidomycin (Fürstner)." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0034.

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Masato Matsugi of Meijo University showed (J. Org. Chem. 2010, 75, 7905) that over five iterations, the fluorous-tagged Ru catalyst 1b was readily recovered and reused for the cyclization of 2 to 3. Hengquan Yang of Shanxi University reported (Chem. Commun. 2010, 46, 8659) that the Hoveyda catalyst 1a encapsulated in mesoporous SBA-1 could also be reused several times. Jean-Marie Basset of KAUST Catalysis Center, Régis M. Gauvin of Université Lille, and Mostafa Taoufik of Université Lyon 1 described (Chem. Commun. 2010, 46, 8944) a W catalyst on silica that was also active for alkene metathesis. Reto Dorta of the University of Zurich, exploring several alternatives, found (J. Am. Chem. Soc. 2010, 132, 15179) that only 4c cyclized cleanly to 5. Karol Grela of the Polish Academy of Sciences showed (Synlett 2010, 2931) that 3-nitropropene (not illustrated) participated in cross-metathesis when catalyst 1c was used. Shawn K. Collins of the Université de Montré al complexed (J. Am. Chem. Soc. 2010, 132, 12790) 6 with a quinolinium salt to direct paracyclophane formation. Min Shi of the Shanghai Institute of Organic Chemistry incorporated (Org. Lett. 2010, 12, 4462) the cyclopropene 8 in cross-metathesis, to give 10. A. Srikrishna of the Indian Institute of Science (Bangalore) constructed (Synlett 2010, 3015) the cyclooctenone 12 by ring-closing metathesis. LuAnne McNulty of Butler University established (J. Org. Chem. 2010, 75, 6001) that a cyclic boronic half acid 15, prepared by ring-closing metathesis, coupled with an iodoalkene 16 to deliver the diene 17 with high geometric control. Gowravaram Sabitha of the Indian Institute of Chemical Technology, Hyderabad, en route to (+)-anamarine 21, observed (Tetrahedron Lett. 2010, 51, 5736) that the tetraacetate 18b would not participate in cross-metathesis. Fortunately, 18a , an earlier intermediate in the synthesis, worked well. Stephen F. Martin of the University of Texas prepared (Org. Lett. 2010, 12, 3622) (±)-pseudotabersonine 24 by way of a spectacular metathesis that converted 22 to 23. Ring-closing alkyne metathesis was a key step in the total synthesis of lactimidomycin 27 reported (J. Am. Chem. Soc. 2010, 132, 14064) by Alois Fürstner of the Max-Planck- Institut Mülheim.
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Conference papers on the topic "Total Synthesis, silicon"

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Yoon, Hui su, and In-Hwan Kim. "Lipozyme TL IM-catalyzed synthesis of γ-linolenic acid rich triacylglycerol from borage oil as a novel strategy." In 2022 AOCS Annual Meeting & Expo. American Oil Chemists' Society (AOCS), 2022. http://dx.doi.org/10.21748/sgec7971.

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Lipozyme TL IM from Thermomyces lanuginosus is widely employed for various enzymatic reactions such as esterification, hydrolysis, and alcoholysis. However, none of the publications is using Lipozyme TL IM as a biocatalyst to synthesize triacylglycerol (TAG) with fatty acid and glycerol because the silica gel carrier in Lipozyme TL IM aggregates with glycerol. Thus, most studies regarding the synthesis of TAG via lipase-catalyzed esterification have employed Novozym 435, one of the most expensive enzymes. In present study, we attempted to synthesize TAG using Lipozyme TL IM with glyceride, instead of glycerol, and fatty acid as a novel strategy; as a result, γ-linolenic acid (GLA) rich TAG was synthesized successfully via esterification using Lipozyme TL IM. In the first step, GLA was enriched into glyceride fraction from borage oil by C. rugosa lipase-catalyzed hydrolysis and the GLA rich glyceride was separated from the reaction mixture using short-path distillation. GLA was enriched up to 45.9% in glyceride fraction from an initial value of 20.6% under the optimum conditions, which are the temperature of 40 °C and the enzyme loading of 0.05% (based on the oil weight of the total substrate). In the second step, GLA rich TAG was synthesized with the GLA rich glyceride, instead of glycerol, and the fatty acid obtained from part of the GLA rich glyceride by saponification using Lipozyme TL IM as a biocatalyst. The optimum conditions were the temperature of 50 °C, the enzyme loading of 10%, and the vacuum level of 5 torr, respectively. Consequently, the maximum TAG conversion of ca. 93% was achieved after 24 h under the optimum condition.
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