Relevant bibliographies by topics / Enone Transposition

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  1. Journal articles
  2. Dissertations / Theses
  3. Book chapters

Academic literature on the topic 'Enone Transposition'

Author: Grafiati
Published: 6 September 2023

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Journal articles on the topic "Enone Transposition"

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Kutney, James P., and Carles Cirera. "The chemistry of thujone. XX. New enantioselective syntheses of Ambrox and epi-Ambrox." Canadian Journal of Chemistry 75, no. 8 (August 1, 1997): 1136–50. http://dx.doi.org/10.1139/v97-136.

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The development of a new synthetic approach to (−)-Ambrox® (37) and epi-Ambrox® (29) using thujone (1) as a chiral synthon, is presented. Thujone (1), a readily available starting material obtained from Western red cedar, can be efficiently converted to β-cyperone (2) and the latter is then chemically elaborated to the key intermediate, the enone 6. A carbonyl transposition of 6 to enone 9 also allows a formal synthesis of (−)-Polywood® (18). Keywords: thujone, β-cyperone, (−)-Ambrox®, epi-Ambrox®, synthesis.
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2

Collins, Jonathan A., Christopher J. Gerry, and Madeleine M. Duncan. "A Chemoenzymatic Formal Synthesis of Epoxyquinols A and B." Synlett 30, no. 19 (October 23, 2019): 2193–97. http://dx.doi.org/10.1055/s-0039-1690216.

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A formal synthesis of epoxyquinols A and B was completed in nine steps starting from benzoic acid. Enantioselectivity was established through an enzymatic arene dihydroxylation reaction performed by whole cells of Ralstonia eutropha B9 expressing benzoate dioxygenase. Subsequent formation of the enone core was facilitated by a Dauben–Michno-type oxidative transposition of an allylic tertiary alcohol.
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3

Ma, Xinghua, Xin Liu, Patrick Yates, Warwick Raverty, Martin G. Banwell, Chenxi Ma, Anthony C. Willis, and Paul D. Carr. "Manipulating the enone moiety of levoglucosenone: 1,3-Transposition reactions including ones leading to isolevoglucosenone." Tetrahedron 74, no. 38 (September 2018): 5000–5011. http://dx.doi.org/10.1016/j.tet.2018.03.023.

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4

Hantos, Susanne M., Sasmita Tripathy, Najma Alibhai, and Tony Durst. "Synthesis of trichiliasterones A and B — 16-Ketosteroids isolated from Trichilia hirta and Trichilia americana." Canadian Journal of Chemistry 79, no. 11 (November 1, 2001): 1747–53. http://dx.doi.org/10.1139/v01-126.

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The syntheses of trichiliasterone A (3β-hydroxypregnan-2,16-dione) and trichiliasterone B (2-hydroxyandrost-1,4-diene-3,16-dione) have been carried out starting from isoandrosterone and testosterone acetate, respectively. In each synthesis the functionality in the D ring was installed prior to working on ring A. In the case of trichiliasterone A, the D ring chemistry involved a Wittig reaction to generate the 17-methylene group, followed by SeO2 oxidation to give an α,β-unsaturated ketone. Reaction with lithium dimethyl cuprate gave the required 17-ethyl-16-keto functionality. A 2,3-epoxy enol acetate served as the key intermediate for the generation of the 2-keto-3-hydroxy functions in ring A. The transposition of the keto function from C-16 to C-17 in the synthesis of trichiliasterone B was accomplished via oxymercuration–demercuration of the Δ16—17 double bond followed by oxidation. The hydroxyl group at C-2 and the additional ring A unsaturation were introduced by lead tetra-acetate treatment of the 3-keto-4-enone function and subsequent air oxidation.Key words: 16-ketosteroids, plant steroids, Trichilia hirta, trichiliasterones.
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5

Athawale, Paresh R., Vishal M. Zade, Gamidi Rama Krishna, and D. Srinivasa Reddy. "Tuning of α-Silyl Carbocation Reactivity into Enone Transposition: Application to the Synthesis of Peribysin D, E-Volkendousin, and E-Guggulsterone." Organic Letters 23, no. 17 (August 13, 2021): 6642–47. http://dx.doi.org/10.1021/acs.orglett.1c02173.

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6

Hudlicky, Jason R., Lukas Werner, Vladislav Semak, Razvan Simionescu, and Tomas Hudlicky. "Dauben–Michno oxidative transposition of allylic cyanohydrins — Enantiomeric switch of (–)-carvone to (+)-carvone*Based on the 2010 Bader Award Lecture." Canadian Journal of Chemistry 89, no. 5 (May 2011): 535–43. http://dx.doi.org/10.1139/v11-026.

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Allylic cyanohydrins were subjected to Dauben–Michno oxidation at low temperatures to provide β-cyanoenones in good to excellent yields. The potential of this oxidative transposition as a means of an enantiomeric switch of enones containing a latent plane of symmetry was tested by conversion of (–)-carvone to its enantiomer.
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7

Baptistella, Lúcia H. B., and Adriana M. Aleixo. "α′-HYDROXY-α,β-UNSATURATED TOSYLHYDRAZONES: PREPARATION AND USE AS INTERMEDIATES FOR CARBONYL AND ENONE TRANSPOSITIONS." Synthetic Communications 32, no. 19 (January 2002): 2937–50. http://dx.doi.org/10.1081/scc-120012982.

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8

Nagasawa, Shota, Yusuke Sasano, and Yoshiharu Iwabuchi. "Catalytic Oxygenative Allylic Transposition of Alkenes into Enones with an Azaadamantane‐Type Oxoammonium Salt Catalyst." Chemistry – A European Journal 23, no. 43 (July 12, 2017): 10276–79. http://dx.doi.org/10.1002/chem.201702512.

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9

Baptistella, Lucia H. B., and Adriana M. Aleixo. "α′-Hydroxy-α,β-unsaturated Tosylhydrazones: Preparation and Use as Intermediates for Carbonyl and Enone Transpositions." ChemInform 34, no. 2 (January 14, 2003). http://dx.doi.org/10.1002/chin.200302152.

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Dissertations / Theses on the topic "Enone Transposition"

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Otoo, Barnabas. "Conjugate Additions and Transposition of the Allylic Alcohols of Enol Ethers of 1, 2-Cyclohexanedione." Digital Commons @ East Tennessee State University, 2010. https://dc.etsu.edu/etd/1748.

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A variety of protected enolic forms of 1, 2-cyclohexanedione was prepared as substrates for conjugate addition studies using organocopper reagents. The sequence involved the enol ether preparation via the enolate, alkylation with an organometalic reagent, and oxidative rearrangement with pyridinium chlorochromate followed by the conjugate addition reactions. Protection of 1, 2-cyclohexanedione was achieved by reacting with chloro tert-butyldimethyl silane and subjected to alkylation. Steric problems were encountered and so an alternative protective group the methoxymethyl acetal was prepared and studied. Alkylation of these derivatives was successful; however, the oxidation was problematic and although evidence for rearrangement was observed in one case, it did not provide the desired ketone.
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Campolo, Damien. "Transfert de chiralité dans les réarrangements en cascade d'ènediynes." Thesis, Aix-Marseille, 2013. http://www.theses.fr/2013AIXM4339/document.

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La synthèse asymétrique d’aza-hétérocycles (tétrahydro-isoquinoléines et naphtodiazépines) a été réalisée grâce à la mise en œuvre d’un processus faisant intervenir des réactions radicalaires et polaires en cascade à partir des ènediynes portant un centre stéréogène. Ce processus implique successivement : la formation d’un ényne-allène (via une migration-1,3 de proton, une réaction d’un alcyne terminal avec un carbénoïde de cuivre, ou encore une réaction d’homologation de Crabbé)/ la cyclisation de Saito-Myers/ le transfert-1,5 d’un atome d’hydrogène/ la recombinaison du biradical résultant. Les deux dernières étapes élémentaires de ce réarrangement étaient idéalement adaptées à l’application d’une stratégie basée sur le phénomène de mémoire de chiralité. Des études mécanistiques basées sur des expériences de marquage isotopique et des calculs théoriques ont permis de mieux comprendre les paramètres qui contrôlent la régio- et la stéréosélectivité de la réaction. L’ambition de contrôler par cette voie, via une double mémoire de chiralité, deux centres stéréogènes nous a conduits à étudier le transfert de la chiralité axiale d’un motif allénique judicieusement substitué. Cette étude a permis de découvrir une cycloisomérisation originale catalysée par le cuivre (I) conduisant à des fulvènes chiraux via un double transfert de chiralité (centrique-axial-centrique)
The asymmetric synthesis of azaheterocycles (tetrahydorisoquinolines and naphthodiazepines) was successfully achieved via the polar/radical cross-over rearrangement of enediynes bearing a stereogenic center. This process involves successively : enyne-allene formation (via 1,3-proton shift, reaction of a terminal alkyne group with carbenoids or Crabbé homologation)/Saito-Myers cyclization/1,5-hydrogen atom transfer/biradical recombination. It was ideally suited to apply a strategy based on the memory of chirality phenomenon. Mechanistic studies based on isotopic labelling and theoretical calculations enabled to go deeper into the understanding of the parameters controlling the regio- and the stereoselectivity of the reaction. The ambition to control two stereogenic centers via double memory of chirality, led us to investigate the transfer of the axial chirality of a designed allenic moiety. This study led to the discovery of an original copper (I)-mediated cycloisomerization leading to chiral fulvenes and proceeding via central-to-axial-to-central double chirality transfer
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Book chapters on the topic "Enone Transposition"

1

Taber, Douglass F. "The Tanino/Miyashita Synthesis of Solanoeclepin A." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0104.

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Building on the Tanino synthesis of glycinoeclepin (Organic Highlights, January 3, 2011), the hatch-stimulating substance for the soybean cyst nematode, Keiji Tanino of Hokkaido University and Masaaki Miyashita, now at Kogakuin University, described (Nat. Chem. 2011, 3, 484) a convergent synthesis of solanoeclepin A 3, the hatch-stimulating substance for the potato cyst nematode. A key step in the synthesis was the diastereoselective Diels-Alder cyclization of 1 to 2. The starting point for the synthesis was the conjugate addition of 5 to 3-methyl cyclohexenone 4, followed by aldol condensation. The secondary acetate corresponding to 6 was readily resolved by lipase hydrolysis. The next challenge was the installation of the angular vinyl group. Enone transposition gave 7, to which vinyl Grignard added with high diastereocontrol, leading to the diol 8. TMSOTf-mediated epoxide rearrangement with concomitant 1,2 vinyl shift then delivered 9. Epoxidation followed by Stork cyclization completed the construction of the cyclobutane 10. The allylic alcohol 12 was enantiomerically pure, so the relative configuration of the sidechain cyclopropane could be set by the Charette protocol. Grieco dehydration of 14 then gave 16, a latent form of the cyclobutanone of 3. Condensation of the ketone 17 with 18 delivered the expected keto enamine, which rearranged nicely on exposure to Tf2O to the aldehyde 19. Diastereoselective addition of the furyl lithium 20 followed by Pd-catalyzed coupling with 21 then completed the assembly of the Diels-Alder substrate 1. The Me2AlCl-mediated intramolecular Diels-Alder cyclization of 1 led to 2 with remarkable diastereocontrol. Oxidation gave 22, that was further oxidized to the protected enol 23. Reduction, alkene cleavage, and protecting group manipulation then set the stage for the final oxidation of 24 to solanoeclepin A 3.
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