Bibliografías temáticas / Vinigrol

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Literatura académica sobre el tema "Vinigrol"

Autor: Grafiati

Publicado: 4 de junio de 2021

Última modificación: 1 de febrero de 2022

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Artículos de revistas sobre el tema "Vinigrol"

Maimone, Thomas J., Jun Shi, Shinji Ashida y Phil S. Baran. "Total Synthesis of Vinigrol". Journal of the American Chemical Society 131, n.º 47 (2 de diciembre de 2009): 17066–67. http://dx.doi.org/10.1021/ja908194b.

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Yang, Qingliang, Jon T. Njardarson, Cristian Draghici y Fang Li. "Total Synthesis of Vinigrol". Angewandte Chemie International Edition 52, n.º 33 (1 de julio de 2013): 8648–51. http://dx.doi.org/10.1002/anie.201304624.

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Yang, Qingliang, Jon T. Njardarson, Cristian Draghici y Fang Li. "Total Synthesis of Vinigrol". Angewandte Chemie 125, n.º 33 (1 de julio de 2013): 8810–13. http://dx.doi.org/10.1002/ange.201304624.

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Wang, Xian-Lei, Yun-Yu Lu, Jie Wang, Xuan Wang, He-Quan Yao, Guo-Qiang Lin y Bing-Feng Sun. "A novel synthetic approach to the bicyclo[5.3.1]undecan-11-one framework of vinigrol". Org. Biomol. Chem. 12, n.º 22 (2014): 3562–66. http://dx.doi.org/10.1039/c4ob00046c.

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A unique approach to the [5.3.1] bicyclic core of vinigrol is described featuring highly stereoselective C–C bond forming reactions through exploring the inherent conformational bias of the cyclooctane-ring system.

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Min, Long, Xiaohong Lin y Chuang-Chuang Li. "Asymmetric Total Synthesis of (−)-Vinigrol". Journal of the American Chemical Society 141, n.º 40 (23 de septiembre de 2019): 15773–78. http://dx.doi.org/10.1021/jacs.9b08983.

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Maimone, Thomas J, Ana-Florina Voica y Phil S Baran. "Ein einfacher Zugang zu Vinigrol". Angewandte Chemie 120, n.º 16 (7 de abril de 2008): 3097–99. http://dx.doi.org/10.1002/ange.200800167.

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Poulin, Jason, Christiane M. Grisé-Bard y Louis Barriault. "A Formal Synthesis of Vinigrol". Angewandte Chemie 124, n.º 9 (19 de enero de 2012): 2153–56. http://dx.doi.org/10.1002/ange.201108779.

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Huters, Alexander D y Neil K Garg. "Synthetic Studies Inspired by Vinigrol". Chemistry - A European Journal 16, n.º 29 (2 de julio de 2010): 8586–95. http://dx.doi.org/10.1002/chem.201000916.

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Maimone, Thomas J, Ana-Florina Voica y Phil S Baran. "A Concise Approach to Vinigrol". Angewandte Chemie International Edition 47, n.º 16 (7 de abril de 2008): 3054–56. http://dx.doi.org/10.1002/anie.200800167.

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Poulin, Jason, Christiane M. Grisé-Bard y Louis Barriault. "A Formal Synthesis of Vinigrol". Angewandte Chemie International Edition 51, n.º 9 (19 de enero de 2012): 2111–14. http://dx.doi.org/10.1002/anie.201108779.

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Tesis sobre el tema "Vinigrol"

Johnstone, Lisa. "Towards the total synthesis of vinigrol". Thesis, Durham University, 2006. http://etheses.dur.ac.uk/2584/.

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Virigrol is a unique tricyclic diterpene containing the unprecedented decahydro-1, 5- butanonapathalene framework and with these unusual structural features it also has varied biological activity, making it a challenging synthetic target. Despite various groups working in this area, there has been no total synthesis published to date. The thesis begins by discussing the challenging aspect of the total synthesis, construction of the 8-membered ring. Three distinct strategies exist for the construction of 8-membered carbocyclęs. C-C-bond forming reactions and ring expansion approaches have been utilised in the syntheses towards Vinigrol to date. However neither method has yet yielded a total synthesis. Ring fragmentation has not been exploited in the synthesis of Vinigrol to date and is a useful synthetic tool since smaller ring systems are easier to construct than their medium ring counterparts. It was envisaged that the 8-membered ring could be installed in a masked form as a series of 6-membered rings and thereby avoiding the normal difficulties associated with medium ring synthesis. Scheme 1. The key reaction of the synthesis was an intramolecular Diels Alder reaction. This thesis describes three related strategies which were utilised in order to afford the masked 8-membered ring which would then enable the tricyclic skeleton of Vinigrol to be obtained.

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Gentric, Lionel. "Approche de la synthèse totale du vinigrol". Palaiseau, Ecole polytechnique, 2002. http://www.theses.fr/2002EPXX0008.

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Le vinigrol est un produit naturel de la famille des diterpénoi͏̈des isolé en 1987 à partir de souches du champignon Virgaria Nigra. Sa synthèse totale se présente comme un objectif très attractif, du fait du spectre de l'activité biologique de la molécule et de l'originalité manifeste de son squelette carboné - le motif le plus caractéristique de la structure est un carbocycle à huit cheinons doublement ponté par deux cycles à six chaînons. A ce jour, aucune synthèse totale du vinigrol n'a été publiée. Notre travail a consisté en l'élaboration du squelette tricyclique complet du produit naturel. La clé de cette approche est un réarrangement d"oxy-Cope anionique qui, à partir d'un alcool allylique, permet de construire efficacement le système tricyclique désiré, dont nous avons ensuite Largement étudié la réactivité. La difficulté majeure de la synthèse, en dehors de la construction proprement dite du squelette de la molécule, réside dans la configuration du centre C-12, au pied du groupe isopropyle. Après de longues recherches, au cours desquelles nous étions convaincus de ne pas pouvoir accéder directement à la configuration (R) souhaitée sur ce centre, nous avons découvert que la construction du squelette du vinigrol par un réarrangement sigmatropique conduisant à la configuration (R) en C-12 est en fait possible, par le réarrangement [3,3] d'un système octatriénique. Cette transformation, encore énigmatique, pourrait être le point de départ de travaux susceptibles de mettre en lumière un nouvel effet de substituant pour le réarrangement d'oxy-Cope anionique, ou de porter un éclairage supplémentaire sur le mécanisme de la réaction. Nous avons mis au point une synthèse en quatorze étapes et 27% de rendement global d'un intermédiaire très avancé, qui offre une perspective bien dégagée vers la synthèse totale du vinigrol.

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Morency, Louis. "Studies toward the total synthesis of vinigrol". Thesis, University of Ottawa (Canada), 2006. http://hdl.handle.net/10393/29366.

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This thesis presents the work done toward the total synthesis of vinigrol. The studies described here are divided into three main approaches. First, the oxy-Cope/Claisen/ene and the oxy-Cope/ene reactions have been developed to provide cis-decalin systems. These methodologies have been applied for the synthesis of the core of vinigrol. Second, a synthetic route that includes the exploitation of the hydroxy-directed Diels-Alder reaction to construct the vinigrol cis-decalin was developed. Two different strategies were developed to close the remaining eight-membered ring: a ring closing metathesis and a Claisen rearrangement. Finally, the sequential hydroxy-directed Diels-Alder/Claisen reaction was adapted for the synthesis of the six- and eight-membered rings of vinigrol.

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Devaux, Jean-François. "Vers la synthèse totale d'un diterpénoïde, le vinigrol". Palaiseau, Ecole polytechnique, 1995. http://www.theses.fr/1995EPXX0013.

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Le vinigrol, diterpène isole en 1987 du champignon microscopique virgaria nigra, possède des activités biologiques intéressantes : c'est notamment un agent antihypertenseur, un inhibiteur d'agrégation plaquettaire, et un antagoniste de tnf (facteur nécrosant de tumeur). Il possède un squelette tricyclique unique en son genre, qui comprend un cycle a huit carbones doublement ponte par deux cycles a six. Notre travail a constitué en la mise au point d'une voie d'accès pour la synthèse du vinigrol. Dans une première partie, nous présentons la première synthèse du squelette decahydro-1,5-butanonaphtalene du vinigrol. La clé de cette approche est un réarrangement d'oxy-cope anionique a partir d'un alcool allylique. Ce dernier a pu être forme avec la bonne configuration par addition stéréosélective d'un organomagnésien vinylique sur une cétone tricyclique, orientée par un groupement hydroxyle de la molécule. Cette synthèse efficace permet d'obtenir plusieurs grammes de l'intermédiaire possédant le squelette du vinigrol en 9 étapes avec un rendement total de l'ordre de 20%. Dans une deuxième partie, nous avons étudié la fonctionnalisation de cet intermédiaire, découvrant ainsi la réactivité toute particulière de cette nouvelle structure tricyclique très compacte. Cette étude a abouti a la synthèse de composes très proches du vinigrol et ouvert la voie de sa synthèse totale.

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Guevel, Ronan. "Synthetic Studies towards Vinigrol Tandem Cope-Cope Rearrangements /". The Ohio State University, 1994. http://rave.ohiolink.edu/etdc/view?acc_num=osu1487850665559446.

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Milgram, Benjamin Charles. "Progress Toward the Total Synthesis of Vinigrol and Hibarimicin B". Thesis, Harvard University, 2013. http://dissertations.umi.com/gsas.harvard:11220.

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Vinigrol is a structurally unique diterpenoid natural product featuring a tricyclo[4.4.4.0.4a,8a]tetradecene carbon skeleton containing eight contiguous stereocenters and a challenging oxygenation pattern. Vinigrol has been demonstrated to possess a wide array of biological activities including tumor necrosis factor (TNF) antagonism, antihypertensive activity, and platelet aggregation inhibitory activity. Our first-generation plan for the synthesis of vinigrol utilized a cascade reaction sequence involving: (1) diastereoselective alkylation of an α-alkenyl-β-ketoester, (2) retro-aldol-aldol equilibration (3) anion-accelerated oxy-Cope rearrangement, and (4) transannular Dieckmann condensation to afford the bicyclo[5.3.1]undecene ring system of vinigrol in a single operation. Discoveries concerning the limitations of this process are disclosed. Our second-generation approach to vinigrol employed a cis-decalin substrate in an alternative cascade reaction sequence, which was expected to deliver the complete tricyclo[4.4.4.0.4a,8a]tetradecene carbon skeleton of vinigrol in one step. An unexpected deviation from the envisioned reaction pathway instead afforded an alternative tricyclic enol silane.
Chemistry and Chemical Biology

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Poulin, Jason. "Formal Synthesis of Vinigrol and Efforts Towards the Total Synthesis of Digitoxigenin". Thèse, Université d'Ottawa / University of Ottawa, 2013. http://hdl.handle.net/10393/23944.

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Vinigrol was isolated in 1987 from the fungal strain Virgaria nigra F-5408 by Hashimoto and co-workers. This compound was identified as having antihypertensive and platelet aggregation properties as well as being recognized as a tumor necrosis factor inhibitor. Aside from its interesting biological activities, vinigrol also possesses a unique structural motif consisting in a decahydro-1,5-butanonaphthalene core decorated with 8 contiguous stereocenters. Despite synthetic efforts by many research groups since its isolation, it wasn’t until 2009 that the first total synthesis of vinigrol was reported by Baran and co-workers. Herein is presented a formal synthesis of this highly compact molecule which relies upon a highly diastereoselective ketal Claisen rearrangement as the stereodefining step and an intramolecular Diels-Alder reaction to access the tricyclic structure of the molecule. (+)-Digitoxigenin is a cardiac glycoside used in the treatment of many ailments such as congestive heart failure. It is a member of the cardenolides, a sub-type of steroid containing certain structural differences such as cis A/B and C/D ring junctions, a tertiary hydroxyl group at C14 and a butenolide substituent at C17. Although a few syntheses of this class of compounds have been reported, general strategies to access their framework is scarce. Herein we report our studies towards the total synthesis of digitoxigenin which rely upon a cascading gold-catalyzed cycloisomerization (or enyne metathesis)/Diels-Alder reaction.

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Efremov, Ivan V. "Enantioselective total syntheses of Teubrevin G and Teubrevin H and studies toward the Enantioselective Total Synthesis of Vinigrol /". The Ohio State University, 2001. http://rave.ohiolink.edu/etdc/view?acc_num=osu1486399160105875.

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Räder, Andreas Franz Bernd [Verfasser], Konrad [Akademischer Betreuer] [Gutachter] Tiefenbacher y Stephan A. [Gutachter] Sieber. "Studien zu einer kurzen Synthese von (–)-Vinigrol und eine Suche nach neuen Fluorquinolon-Antibiotika durch eine Wasserstoffbrücken-vermittelte kombinatorische Bibliothek / Andreas Franz Bernd Räder ; Gutachter: Konrad Tiefenbacher, Stephan A. Sieber ; Betreuer: Konrad Tiefenbacher". München : Universitätsbibliothek der TU München, 2016. http://d-nb.info/1127728539/34.

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Brekan, Jonathan Alan. "Application of carbon-hydrogen activation/Cope rearrangement methodology towards the total syntheses of Pseudopterosin, Elisabethatriene and Vinigrol". 2008. http://proquest.umi.com/pqdweb?did=1594481381&sid=4&Fmt=2&clientId=39334&RQT=309&VName=PQD.

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Thesis (Ph.D.)--State University of New York at Buffalo, 2008.
Title from PDF title page (viewed on Jan. 15, 2009) Available through UMI ProQuest Digital Dissertations. Thesis adviser: Davies, Huw M. Includes bibliographical references.

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Capítulos de libros sobre el tema "Vinigrol"

Brahmachari, Goutam. "Vinigrol". En Total Synthesis of Bioactive Natural Products, 293–300. Elsevier, 2019. http://dx.doi.org/10.1016/b978-0-08-102822-3.00056-0.

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Taber, Douglass F. "The Baran Synthesis of Vinigrol". En Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0091.

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The diterpene vinigrol 3, isolated from Virgaria nigra F-5408, has eluded total synthesis for more than 20 years. Attempts to construct the four-carbon bridge on a preformed cis-decalin have been unavailing. Phil S. Baran of Scripps/La Jolla solved (Angewandte Chem. Int. Ed. 2008, 47, 3054; J. Am. Chem. Soc. 2009, 131, 17066) this problem by adding the extra C-C bond of 1, which could then be cleaved in course of a Grob fragmentation, leading to 2. The preparation of 1 started with the dihydroresorcinol derivative 4. Diels-Alder addition of the ester 5 gave 6, with a modest 2:1 dr. Addition of allyl MgCl to the derived aldehyde 7 proceeded with 6:1 dr. The resulting triene was conformationally sufficiently constrained that cyclization to 8 proceeded at room temperature over 2 weeks, or more conveniently at 105°C for 90 minutes. With 8 in hand, oxidation to the ketone allowed installation of the additional methyl group of 9. Desilylation followed by OH-directed reduction set the relative configuration of 1 correctly for the Grob fragmentation to the Z -alkene 2. There were two remaining problems in the synthesis. The alkene of 2 had to be converted to the methylated tertiary alcohol, and the ketone had to be elaborated to the ene diol. Though seemingly straightforward, the congested tricyclic skeleton of 2 made many common transformations difficult. The solution to the first problem was found in the selective dipolar addition of bromonitrile oxide. Reduction of the ketone then enabled HO-directed hydrogenation of the alkene, which otherwise was resistant. Dehydration followed by reduction with LiAlH4 gave the desired methyl group bearing a primary amine, which was removed by free radical reduction of the corresponding isonitrile, to give 12. With 12 in hand, the end of the synthesis appeared to be in sight. In fact, the reduction of a variety of oxidized intermediates proved difficult. In the end, a sequence that did not require reduction proved effective. Dihydroxylation of 12 gave a diol, selective oxidation of which delivered the α-hydroxy ketone 13. Formation of the trisylhydrazone followed by Shapiro reaction gave the intermediate alkenyl anion, which was trapped with formaldehyde to give the long-sought vinigrol 3.

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Taber, Douglass F. "The Njardarson Synthesis of Vinigrol". En Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0086.

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The diterpene vinigrol 3, isolated from Virgaria nigra F-5408, is a tumor necrosis factor (TNF) inhibitor. Jon T. Njardarson of the University of Arizona envisioned (Angew. Chem. Int. Ed. 2013, 52, 8648) that Wharton fragmentation of 1 could deliver 2, suitably functionalized for elaboration to 3. The tetracyclic 1 was prepared by the triply-convergent assembly of the phenol 11. Addition of allyl magnesium bromide to 4 proceeded with high regio- and geometric selectivity, to give an alcohol that was methylated, then iodinated with inversion to give 5. Condensation of the phosphonate 7 with the derived aldehyde 6 led to the alcohol 8, that was coupled under Mitsunobu conditions with the phenol 9 to give 10. Oxidation of 11 gave an intermediate that underwent intramolecular Diels–Alder cycloaddition to deliver 12. On exposure to the Pd catalyst, 12 cyclized to the diene 13. On exposure to tBuOK/ tBuOH, the mesylate 1 smoothly fragmented to the hoped-for ketone 2. Although this has been referred to as a Grob fragmentation, in fact this reaction was developed (J. Org. Chem. 1961, 26, 4781) by Peter S. Wharton, then at the University of Wisconsin, and would more properly bear his name. Subsequent transformations took advantage of the hindered nature of the trisubstituted alkene of 2. Hydrogenation of the disubstituted alkene proceeded selectively, to give an intermediate that was condensed with 14, leading to the enone 15. Two more selective hydrogenations, with the Wittig methylenation in between, completed the construction of the pendant isopropyl group. Once the isopropyl group was installed, what remained was the oxidation of 16 to 19. The epoxidation of 17 proceeded with high facial selectivity, to give an intermediate that was carried on by iodination and reduction to the alcohol 18. Allylic oxidation converted 18 into 19, that was deprotected to give Vinigrol 3. It is instructive to compare and contrast this approach to vinigrol 3 with the two that we have previously highlighted (OHL September 6, 2010; December 24, 2012). Each strategy offers its own advantages.

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Forberg, M. J. C. y L. Barriault. "The Long and Winding Road of the Vinigrol Synthesis". En Strategies and Tactics in Organic Synthesis, 1–35. Elsevier, 2016. http://dx.doi.org/10.1016/b978-0-08-100756-3.00001-7.

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Draghici, Cristian y Jon T. Njardarson. "The Realization of an Oxidative Dearomatization–Intramolecular Diels–Alder Route to Vinigrol". En Strategies and Tactics in Organic Synthesis, 335–76. Elsevier, 2015. http://dx.doi.org/10.1016/b978-0-08-100023-6.00011-7.

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Taber, Douglass F. "Diels-Alder Cycloaddition: Fawcettimine (Williams), Apiosporic Acid (Helmchen), Marginatone (Abad- Somovilla), Okilactomycin (Hoye), Vinigrol (Barriault), Plakotenin (Bihlmeier/Klopper)". En Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0079.

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Highly substituted dienes and dienophiles are often reluctant participants in intermolecular Diels-Alder cycloaddition. Nevertheless, Robert M. Williams of Colorado State University, in the course of a synthesis of fawcettimine 4, was able (J. Org. Chem. 2012, 77, 4801) to prepare 3 by combining the enone 1 with the diene 2. Günter Helmchen of the Universität Heidelberg set (J. Org. Chem. 2012, 77, 4491) the single stereogenic center of 5 by Ir-catalyzed allylic alkylation. The Lewis acid that promoted the cycloaddition also conveniently removed the trityl protecting group, leading to 6, that was saponified to apiosporic acid 7. Antonio Abad-Somovilla of the Universidad de Valencia prepared (J. Org. Chem. 2012, 77, 5664) the triene 8 in enantiomerically pure form from carvone. Despite the additional substitution on the diene, cycloaddition proceeded smoothly to give 9, which was carried on to marginatone 10. One could envision that okilactomycin 13 could be formed by an intramolecular Diels-Alder cycloaddition. Thomas R. Hoye of the University of Minnesota observed (Org. Lett. 2012, 14, 828) that the tetraene tetronic acid corresponding to 11 was inert, but that the methyl ether 11 cyclized smoothly to 12. Demethylation then gave the natural product The complex polycyclic structure of vinigrol 16 challenged organic synthesis chemists for many years, until a route was established by Phil Baran of Scripps/La Jolla (Highlights September 6, 2010). Louis Barriault cyclized (Angew. Chem. Int. Ed. 2012, 51, 2111) 14 to 15 en route to a late intermediate in the Baran synthesis It had been hypothesized that the natural product plakotenin 19 was formed naturally from a tetraene corresponding to 17. The tetraene 17 was prepared and the cyclization was successful, “confirming” both the structure of the natural product and the biosynthetic hypothesis. Angela Bihlmeier and Wim Klopper of the Karlsruhe Institute of Technology calculated (J. Am. Chem. Soc. 2012, 134, 2154) the relative energies of the four competing transition states for the cyclization, leading to a correction of the structure of 18, and so of the natural product 19.

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Taber, Douglass F. "Diels–Alder Cycloaddition: Nicolaioidesin B (Coster), Lycorine (Cho), Bucidirasin A (Nakada), Maoecrystal V (Thomson), Kuwanon J (Wulff/Lei), Vinigrol (Kaliappan)". En Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0079.

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β-Ocimene 2 is an inexpensive Diels–Alder diene. En route to nicolaioidesin B 4, Mark J. Coster of Griffith University showed (Tetrahedron Lett. 2014, 55, 6864) that the Weinreb amide 1 added to the E isomer of 2 with high selectivity, to give 3. The alkaloid lycorine 8 is found throughout the Amaryllidaceae. Cheon-Gyu Cho of Hanyang University developed (Org. Lett. 2014, 16, 5718) a succinct route to 8 based on the use of the boryl styrene 5 as a Diels–Alder dienophile. Masahisa Nakada of Waseda University (Org. Lett. 2014, 16, 4734) prepared the enantiomerically-pure enone 9 by way of a baker’s yeast reduction of a prochiral diketone. Diels–Alder addition to 10 led to 11, that was carried on to bucidirasin A 12. Regan J. Thomson of Northwestern University prepared (J. Am. Chem. Soc. 2014, 136, 17750) the triene 13 by asymmetric epoxidation of a prochiral enone. Diels–Alder addition of the very reactive nitroethylene to give 14 completed the carbon skeleton of maoecrystal V 15. William D. Wulff of Michigan State University and Xiaoguang Lei of Peking University optimized (Angew. Chem. Int. Ed. 2014, 53, 9257) the organocatalyzed Diels–Alder cycloaddition of 17 to the diene 16. Deprotection then completed the synthesis of the prenylflavonoid kuwanon J 18. In 2012, Barriault described (OHL 20121224) the conversion of 20 to the complex diterpene vinigrol 21. Krishna P. Paliappan of the Indian Institute of Technology Bombay showed (Org. Lett. 2014, 16, 5540) that the triene precursor to 20 could be prepared by ring-closing metathesis of 19. In the absence of ethylene, a different product was formed.

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