Relevant bibliographies by topics / Bicyclo [5,2,1] décène

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  2. Dissertations / Theses
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Academic literature on the topic 'Bicyclo [5,2,1] décène'

Author: Grafiati
Published: 4 June 2021
Last updated: 17 February 2022

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Journal articles on the topic "Bicyclo [5,2,1] décène"

1

Bonnaud, B., R. Leyssens, R. Viani, J. P. Aycard, and M. Monnier. "Dicarbonitrileméthylène-2 diméthyl-8,9 oxo-5 bicyclo[4.4.0]décène-8-cis." Acta Crystallographica Section C Crystal Structure Communications 43, no. 11 (November 15, 1987): 2248–49. http://dx.doi.org/10.1107/s0108270187088206.

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Nielsen, P., and F. Tarding. "The Metabolic Fate of 5-(bicyclo-3, 2, 1-oct-2-en-2-yl)-5-ethyl Barbituric Acid, (Reposal ®)." Acta Pharmacologica et Toxicologica 26, no. 6 (March 13, 2009): 521–30. http://dx.doi.org/10.1111/j.1600-0773.1968.tb00471.x.

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3

Pachuta-Stec, Anna, Urszula Kosikowska, Anna Chodkowska, Monika Pitucha, Anna Malm, and Ewa Jagiełło-Wójtowicz. "Biological Activity of Novel N-Substituted Amides of endo-3- (3-Methylthio-1,2,4-triazol-5-yl)bicyclo[2.2.1]hept-5-ene-2- carboxylic Acid and N-Substituted Amides of 1-(5-Methylthio- 1,2,4-triazol-3-yl)cyclohexane-2-carboxylic Acids." Zeitschrift für Naturforschung C 67, no. 3-4 (April 1, 2012): 123–28. http://dx.doi.org/10.1515/znc-2012-3-403.

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N-Substituted amides of endo-3-(3-methylthio-1,2,4-triazol-5-yl)bicyclo[2.2.1]hept-5-ene- 2-carboxylic acid and 1-(5-methylthio-1,2,4-triazol-3-yl)cyclohexane-2-carboxylic acid were prepared by the condensation reaction of endo-S-methyl-N1-(bicyclo[2.2.1]hept-5-ene-2,3- dicarbonyl)isothiosemicarbazide and S-methyl-N1-(cyclohexane-2,3-dicarbonyl)isothiosemicarbazide with primary amines. The synthesized compounds were screened for their microbiological and pharmacological activities
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4

Liu, Qi Mei, and Wan Xi Peng. "80°С-Based TD-GC/MS Analysis of Chemical Components from Branches of Cinnamomum camphora." Key Engineering Materials 480-481 (June 2011): 466–71. http://dx.doi.org/10.4028/www.scientific.net/kem.480-481.466.

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The analytical result by 80°С-based TD-GC/MS showed that 65 peaks were obtained from the helium volatiles from the fresh branches of Cinnamomum camphora and 60 chemical compounds were identified. The results showed that the main components were as: 1,3-Benzodioxole, 5-(2-propenyl)- (12.629%), Tricyclo[2.2.1.0(2,6)]heptane, 1,7-dimethyl-7-(4-methyl-3-pentenyl)-, (-)- (10.302%), 3-Cyclohexene-1-methanol, .alpha.,.alpha.4-trimethyl- (9.084%), Bicyclo[2.2.1] heptan-2-one, 1,7,7-trimethyl-, (1R)- (7.406%), Nerolidol (6.695%), Bicyclo[2.2.1]heptane, 2-methyl-3-methylene-2-(4-methyl-3-pentenyl)-, (1S-exo)- (6.017%), Bicyclo[2.2.1]heptan-2-one, 1,7,7-trimethyl-, (.+/-.)- (4.885%), Bicyclo[3.1.1]hept-2-ene, 2,6-dimethyl-6-(4-methyl-3-pentenyl)- (4.680%), Naphthalene, 1,2,3,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-, (1S-cis)- (4.139%), 3-Cyclohexen-1-ol, 4-methyl-1-(1-methylethyl)-, (R)- (3.538%), Copaene (2.749%), Bicyclo[2.2.1] heptan-2-ol, 1,7,7-trimethyl-, (1S-endo)- (2.643%), Acetic acid, 1,7,7-trimethyl-bicyclo [2.2.1]hept-2-yl ester (2.536%), Cyclohexane, bromo- (2.530%), 1,6,10-Dodecatriene, 7,11- dimethyl-3-methylene-, (E)- (1.725%), Naphthalene, 1,2,3,4,4a,5,6,8a-octahydro-7-methyl-4- methylene-1-(1-methylethyl)-, (1.alpha.,4a.beta.,8a.alpha.)- (1.265%), Bicyclo[4.4.0]dec-1-ene, 2-isopropyl-5-methyl-9-methylene- (1.174%), (-)-Isosativene (1.149%), 11-Tetradecen-1-ol acetate (1.118%), .alpha.-Cadinol (1.061%), etc. The analytical result suggested that the helium volatiles from the fresh branches of C. camphora could be used as industrial materials of biomedicines, spicery and food industry.
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Petrov, Viacheslav A. "Stereoselective synthesis of 3-[(perfluoroprop-1-en-2-yl)bicyclo[2.2.1]-hept-5-en-2-yl]sulfanes." Mendeleev Communications 16, no. 3 (January 2006): 155–57. http://dx.doi.org/10.1070/mc2006v016n03abeh002327.

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Bourhis, Mireille, René Golse, Michel Goursolle, and Philippe Picard. "Synthesis of new norbornenones with the aminoester group methyl bicyclo [2-2-1] hept 5-ene 7-one 1-amino 2-carboxylates." Tetrahedron Letters 26, no. 29 (January 1985): 3445–48. http://dx.doi.org/10.1016/s0040-4039(00)98660-x.

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7

Ahlenstiel, Eckart, Wolfgang Kliegel, Steven J. Rettig, and James Trotter. "Structural studies of organoboron compounds. LVII. Synthesis and structure of bicyclic boron-nitrogen betaines. 1-Methyl-5-(3-nitrophenyl)-4,6,9-trioxa-1-azonia-5-boratabicyclo[3.3.1]nonane and 3,3,4-trimethyl-1-(3-nitrophenyl)-2,6,7-trioxa-3-azonia-1-boratabicyclo[2.2.2]octane." Canadian Journal of Chemistry 71, no. 2 (February 1, 1993): 263–71. http://dx.doi.org/10.1139/v93-038.

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The syntheses and structures of the bicyclic boron-nitrogen betaines 1-methyl-5-(3-nitrophenyl)-4,6,9-trioxa-1-azonia-5-boratabicyclo[3.3.1]nonane, 7a, and 3,3,4-trimethyl-1-(3-nitrophenyl)-2,6,7-trioxa-3-azonia-1-boratabicyclo[2.2.2]-octane, 14a, are reported. Crystals of 7a are orthorhombic, a = 20.256(2), b = 37.652(2), c = 6.642(1) Å, Z = 16, space group Fdd2, and those of 14a are orthorhombic, a = 21.402(2), b = 11.334(3), c = 11.248(2) Å, Z = 8, space group Pbca. The structures were solved by direct methods and were refined by full-matrix least-squares procedures to R = 0.038 and 0.045 (Rw = 0.036 and 0.053) for 975 and 1646 reflections with I ≥ 3σ(F2), respectively. The X-ray analyses establish the bicyclo[3.3.1]nonane and bicyclo[2.2.2]octane "cage" structures for 7a and 14a, respectively. Bond lengths involving the tetrahedral boron atom are (N)O—B = 1.519(5), (C)O—B = 1.444(6) and 1.443(6), C(aryl)—B = 1.602(5) Å for 7a; and (N)O—B = 1.530(3), (C)O—B = 1.446(3) and 1.455(3), C(aryl)—B = 1.608(3) Å for 14a. Weak [Formula: see text] interactions are the main feature of the crystal packing arrangements of both compounds.
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Werstiuk, Nick Henry, and Chandra Deo Roy. "Experimental and AM1 calculational studies of the deprotonation of bicyclo[2.2.2]octane-2,5-dione and bicyclo[2.2.2]octane-2,6-dione: a study of homoconjugation, inductive, and steric effects on the rates and diastereoselectivities of α enolization." Canadian Journal of Chemistry 73, no. 3 (March 1, 1995): 460–63. http://dx.doi.org/10.1139/v95-060.

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The kinetics of NaOD-catalyzed H/D exchange (enolization) at C3 α to the carbonyl group of bicyclo[2.2.2]octane-2,5-dione (1) and bicyclo[2.2.2]octane-2,6-dione (2) have been studied in 60:40 (v/v) dioxane–D2O at 25.0 °C. The second-order rate constants for exchange are (9.7 ± 1.5) × 10−1 and (3.4 ± 1.2) × 10−5 L mol−1 s−1 for 1 and 2, respectively. Thus, 1, exchanges 76 times faster than bicyclo[2.2.2]octan-2-one (3) (k = (1.27 ± 0.02) × 10−2 L mol−1 s−1), but the 2,6-dione 2 unexpectedly is much less reactive (2.7 × 10−3) than the monoketone. Unlike the large exo selectivity of 658 observed in the case of bicyclo[2.2.1]heptan-2-one, small and opposite selectivities, exo (1.2) for 1 and endo (2.1) for 2, are found for the isomeric [2.2.2] ketones. The results indicate that the incipient enolate of 1 is stabilized by a polar effect of the β carbonyl group at C5, not by homoconjugation. The source of the surprising low reactivity of 2 is unknown at this stage. The small diastereoselectivities, exo (1.2) for 1 and endo (2.1) for 2, correlate with relative energies of the diastereomeric pyramidal enolates calculated with AM1. Keywords: enolization, bicyclo[2.2.2]octane-2,5-dione, bicyclo[2.2.2]octane-2,6-dione, AM1, thermodynamic acidities.
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Werstiuk, N. H., S. Yeroushalmi, and Hong Guan-Lin. "Synthesis of bicyclic diones and thiones. Facile methylation of the enolates of bicyclo[2.2.1]heptane-2,5-dione and bicyclo[2.2.2]octane-2,5-dione. An AM1 computational study of bicyclic enolates." Canadian Journal of Chemistry 70, no. 3 (March 1, 1992): 974–80. http://dx.doi.org/10.1139/v92-130.

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A group of bicyclic ketones and thiones have been synthesized for homenolization studies. Bicyclo[2.2.1]heptane-2,5-dione (6) undergoes unusually rapid tetramethylation giving 3,3,6,6-tetramethylbicyclo[2.2.1]heptane-2,5-dione (1) in good yield. Treatment of 1 with P2S5 in xylene gave 3,3,6,6-tetramethylbicyclo[2.2.1]heptane-2,5-dithione (2) and 3,3,6,6-tetramethyl 15-oxo-bicyclo[2.2.1]heptane-2-thione (3), which was converted into 4 with Raney nickel. Bicyclo[2,2,2]octane-2,5-dione (7), prepared via a Diels–Alder reaction between 2-trimethylsilyloxy-1,3-cyclohexadiene and and α-acetoxyacrylonitrile followed by a one-step desilylation/hydrolysis, also undergoes facile tetramethylation giving 3,3,6,6-tetramethylbicyclo[2.2.2]octane-2,5-dione (5) in good yield. AM1 calculations were carried out on the α-enolates of bicyclo[2.2.1]heptan-2-one, 6, 5-methylidenebicyclo[2.2.1]heptan-2-one, and 4-acetylbicyclo[2.2.1]-heptan-2-one in an attempt to gain information on the source of the enhanced acidity of the C-3 hydrogens of 6 and 7. Keywords: bicyclic ketones, thiones, synthesis.
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Liu, Qi Mei, Dang Quan Zhang, Kuan Peng, and Wan Xi Peng. "Deep Analysis on Bioindustry Prospects of 40°С Volatiles of Cinnamomum camphora Branches." Key Engineering Materials 480-481 (June 2011): 266–71. http://dx.doi.org/10.4028/www.scientific.net/kem.480-481.266.

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Cinnamomum camphora has been used to heal some specific diseases in the Chinese Folk for a long time. In order to explore the wide utilization in biomedicine and spicery, the chemical components of helium volatiles from the fresh branches of C. camphora were studied by TD-GC/MS. The analytical result by TD-GC/MS showed that 50 peaks were obtained from the helium volatiles from the fresh branches of C. camphora and 46 chemical compounds representing 99.993% of the total areas were identified. The results showed that the main components were as: Bicyclo[2.2.1]heptan-2-one, 1,7,7-trimethyl-, (1R)- (9.620%), 3-Cyclohexene-1- methanol, .alpha.,.alpha.4-trimethyl- (9.425%), 1,3-Benzodioxole, 5-(2-propenyl)- (8.223%), Bicyclo[2.2.1]heptane, 2-methyl-3-methylene-2-(4-methyl-3-pentenyl)-, (1S-exo)- (7.541%), Tricyclo[2.2.1.0(2,6)]heptane, 1,7-dimethyl-7-(4-methyl-3-pentenyl)-, (-)- (6.884%), Bicyclo[3.1.1] hept-2-ene, 2,6-dimethyl-6-(4-methyl-3-pentenyl)- (6.050%), Bicyclo[2.2.1]heptan-2-one, 1,7,7- trimethyl-, (1S)- (4.678%), 1,3-Benzodioxole, 5-(2-propenyl)- (4.500%), Naphthalene, 1,2,3,5,6,8a- hexahydro-4,7-dimethyl-1-(1-methylethyl)-, (1S-cis)- (4.491%), 3-Cyclohexen-1-ol, 4-methyl-1- (1-methylethyl)-, (R)- (4.254%), Copaene (4.120%), Tricyclo[2.2.1.0(2,6)]heptane, 1,7-dimethyl-7- (4-methyl-3-pentenyl)-, (-)- (4.097%), Acetic acid, 1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester (3.574%), Borneol 3.334%), 3-(4-N,N-Dimethylaminophenyl)propenoic acid, 2- (diethoxyphosphinyl)-, ethyl ester (2.809%), Eucalyptol (2.096%), 1,6,10-Dodecatriene, 7,11- dimethyl-3-methylene-, (Z)- (1.885%), (-)-Isosativene (1.664%), 1,6,10-Dodecatrien-3-ol, 3,7,11-trimethyl- (1.407%), Cyclohexene, 1-methyl-4-(5-methyl-1-methylene-4-hexenyl)-, (S)- (1.218%), 1,4-Methanoazulene, decahydro-4,8,8-trimethyl-9-methylene-, [1S-(1.alpha.,3a.beta., 4.alpha.,8a.beta.)]- (1.174%), .alpha.-Caryophyllene (1.156%), etc. The analytical result suggested that the helium volatiles from the fresh branches of C. camphora can be applicable to biomedicine and spicery industrial materials.
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Dissertations / Theses on the topic "Bicyclo [5,2,1] décène"

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Benchikh-Le-Hocine, Mohamed El Ouard. "Contribution à la synthèse totale des diterpènes tricycliques de type taxane." Paris 11, 1988. http://www.theses.fr/1988PA112177.

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L'objectif de cette thèse est de mettre au point une nouvelle méthode de synthèse de sous-structures du taxane, groupe des diterpènes dont certains possèdent des activités antileucémique et antitumorale prononcées. La première partie de ce travail décrit la préparation du triméthyl-4, 10, 10 bicyclo [5, 2, 1] décèn-3 dione-2,6, modèle simplifié comportant les cycles A et 8 convenablement fonctionnalisés. Une étude systématique del'addition photochimique [2 + 2] de l'allène sur les dicétones-1,3 et leurs dérivés, a permis de mettre en évidence l'effet du substituant sur la régiosélectivité de la réaction. Le réarrangement moléculaire (acido-catalysé ou basique) de ces adduits photochimiques conduit à la formation du triméthyl-4, 10, 10 bicyclo [5, 2, 1] décèn-3 dione-2,6. La deuxième partie décrit la préparation de l'hydroxy-2 triméthyl-1, 4, 4 dioxalan-7 bicyclo [6,4,0]dodécadione-3,11 comportant les cycles 8 et C du squelette taxane, par une réaction de photocycloaddition [2 + 2]de l'acétoxy-1 méthyl-2 dioxal n-5 hexène. Au cours de ce travail, nous avons pu montrer la complexité des réactions de photo cyclo addition [2 + 2] et les réactions d'alkylation appliquées à des systèmes possédant des cycles à 8 chaînons.
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LAKODEY, ALINE. "Synthese de systemes bicyclo(5. 1. 0) octeniques fonctionnalises. Thermolyses de systemes 1-carbethoxy bicyclo(5. 1. 0) oct-2-eniques." Université Louis Pasteur (Strasbourg) (1971-2008), 1992. http://www.theses.fr/1992STR13111.

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Ce memoire decrit une nouvelle synthese de systemes bicyclo(5. 1. 0) octeniques fonctionnalises au depart d'esters cycloheptadieniques eux-memes obtenus par cycloaddition (2+2) formelle de propiolate d'ethyle sur des enamines de cyclopentanone et d'indanone suivie d'une ouverture de cycle des cyclobutenes formes et d'une desamination reductive. Ces esters cycloheptadieniques reagissent avec divers diazoalcanes (2-diazo propane, diazomethane) pour conduire aux delta-1 pyrazolines correspondantes dont les traitements thermiques ou photochimiques fournissent les systemes bicyclo(5. 1. 0) octeniques attendus. L'elimination du groupe ester situe a la jonction de cycle de ces systemes bicycliques, critique a priori, a ete realisee avec succes, ce qui permet d'envisager l'application de cette nouvelle methode a la synthese de produits naturels. Par ailleurs, une nouvelle transposition cationique permettant de passer d'un systeme bicyclo(5. 1. 0) octenique a un systeme bicyclo(3. 2. 1) octenique a pu etre mise en evidence au cours de ce travail. L'action d'un exces de dioxyde de selenium sur un systeme benzobicyclo(5. 1. 0) octenique nous a egalement permis de decouvrir une nouvelle voie d'acces aux derives benzoheptafulveniques. Enfin, la thermolyse eclair des differents systeme bicyclo(5. 1. 0) octeniques nous a conduit a des migrations sigmatropiques homo(1,5) d'hydrogene plutot qu'au rearrangement des structures vinylcyclopropaniques en cyclopentenes
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Zaid, Abdelhamid. "Préparation et activité pharmacologique de l'anisyl-5 triméthyl-1,9,9 oxa-3 aza-4 bicyclo [4. 2. 1] nonane et de ses dérivés amino-acylés." Montpellier 1, 1987. http://www.theses.fr/1987MON13514.

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Chreim, Yamama. "Synthese de polymeres organosilicies par polycondensation de dienes polycycliques." Université Louis Pasteur (Strasbourg) (1971-2008), 1986. http://www.theses.fr/1986STR13134.

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Polycondensation de molecules diinsaturees, mono- ou polycycliques avec des molecules disilylees (hydrosilylation des doubles liaisons par des fonctions si-h. Les polymeres ont des masses moleculaires comprises entre 3000 et 25000. Stabilite thermique jusqu'a 450**(o)c
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Yang, Ming-Shyong, and 楊明雄. "The Photochemical Competition Reactions of 1, 3, 3-trimethyl- bicyclo[2.2.2]oct-7-en-2, 5-dione Derivatives." Thesis, 1994. http://ndltd.ncl.edu.tw/handle/61963605798314518767.

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Yang, Ming-Xiong, and 楊明雄. "The Photochemical Competition Reactions of 1, 3, 3-trimethyl- bicyclo[2.2.2]oct-7-en-2, 5-dione Derivatives." Thesis, 1994. http://ndltd.ncl.edu.tw/handle/37206652396846371667.

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Books on the topic "Bicyclo [5,2,1] décène"

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Wempe, Michael F. The experimental and theoretical study of the acid catalyzed transannular rearrangement of 5-cyclodecynone to Bicyclo[4.4.0]-1(6)-decen-2-one. 1996.

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Book chapters on the topic "Bicyclo [5,2,1] décène"

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"Bicyclo[3.3.0]octa-1(5),2-diene to Bicyclo[2.2.1]heptan-7-ium." In Substance Index, edited by Backes, Fröhlich, and Padeken. Stuttgart: Georg Thieme Verlag, 2000. http://dx.doi.org/10.1055/b-0035-114013.

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Azbel, B. I., N. F. Goldshleger, E. T. Epelbaum, Yu Yu Yampolskii, M. L. Khidekel, Ya I. Isakov, and Kh M. Minachev. "Catalytic Properties of a Zeolite System in Bicyclo [2. 2. 1] Hepta-2, 5-Diene Reactions." In Studies in Surface Science and Catalysis, 1407–12. Elsevier, 1989. http://dx.doi.org/10.1016/s0167-2991(08)62025-x.

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"Bicyclo[3.2.0]hept-1(5)-ene to 6,7-Dioxabicyclo[3.2.0]hept-2-ene." In Substance Index, edited by Backes, Fröhlich, and Padeken. Stuttgart: Georg Thieme Verlag, 2000. http://dx.doi.org/10.1055/b-0035-114007.

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"Table IV: Volatile compounds identified in the dust of swine confinement units Hydrocarbons Ketones Hexane 1) Acetone 4) «t-Pinen 1) Butanone 4) Limonen 1) Pentanone 4) 3,7,7-Trimethyl -Octanone 4) bicyclo (3,1,1)-l-0ctene-3-one 4) 2-Hepten 1) Benzene 1) Acids Toluene 1) Acetic 4)5)6) Alcohols Propionic 4)5)6) i-Butyric 1)5)6) 1-Pentanol 1) Butyric 4)5)6) 1-Heptanol 1) 1-Valeric 5)6) 4-Methylcyclo-Valeric 4)5)6) hexanol 1) Hexanoic 4)5) 2-Ethylhexanol 1) Heptanoic 4) Octanoic 4) Phenols Nonanoic 4) Decanoic 4) Phenol 1)3)6) Undecanoic 4) p-Cresol 3)4)6) Dodecanoic 4) o-Cresol 1) Laurie 3) p-Ethylphenol 3)6) Tridecanoic 4) o-Ethylphenol 4) Tetradecanoic 4) m-Ethylphenol 4) Benzoic 4) Phenyl acetic 3)4) Indoles 3-Phenyl propionic 3) Hydrocinnamic 4) Indole 2)6) Skatole 2)3)6) Miscellaneous Compounds Aldehydes 2-Pentylfuran 3) Vanillin 3) Butanal 4) 2-Butenal 4) Pentanal 4) 2-Pentenal 4) Hexanal 1)3)4) 1) = WEURMAN (13) 2-Hexenal 4) 2) = TRAVIS and ELLIOTT (31) Heptanal 1)3) 2-Heptenal 4) 3) = HAMMOND et al. (30) 2.4-Heptadienal 3)4) 4) = HAMMOND et al. (40) Nonanal 3) 2-Nonenal 3) 5) = AENGST (33) 2.4-Nonadienal 3)4) 6) = HARTUNG (34) Decanal 4) 2.4-Decadienal 3)4) Benzaldehyde 1)4)." In Odour Prevention and Control of Organic Sludge and Livestock Farming, 344. CRC Press, 1986. http://dx.doi.org/10.1201/9781482286311-138.

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Taber, Douglass. "Total Synthesis by Alkene Metathesis: Amphidinolide X (Urpí/Vilarrasa), Dactylolide (Jennings), Cytotrienin A (Hayashi), Lepadin B (Charette), Blumiolide C (Altmann)." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0031.

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To assemble the framework of the cytotoxic macrolide Amphidinolide X 3, Fèlix Urpí and Jaume Vilarrasa of the Universitat de Barcelona devised (Organic Lett. 2008, 10, 5191) the ring-closing metathesis of the alkenyl silane 1. No Ru catalyst was effective, but the Schrock Mo catalyst worked well. In the course of a synthesis of (-)-Dactylolide 6, Michael P. Jennings of the University of Alabama offered (J. Org. Chem. 2008, 73, 5965) a timely reminder of the particular reactivity of allylic alcohols in ring-closing metathesis. The cyclization of 4 to 5 proceeded smoothly, but attempted ring closing of the corresponding bis silyl ether failed. Polyenes such as ( + )-Cytotrienin A 8 are notoriously unstable. It is remarkable that Yujiro Hayashi of the Tokyo University of Science could (Angew. Chem. Int. Ed. 2008, 47, 6657) assemble the triene of 8 by the ring-closing metathesis of the highly functionalized precursor 7. Bicyclo [2.2.2] structures such as 9 are readily available by the addition of, in this case, methyl acrylate to an enantiomerically-pure 2-methylated dihydropyridine. André B. Charette of the Université de Montréal found (J. Am. Chem. Soc. 2008, 130, 13873) that 9 responded well to ring-opening/ring-closing metathesis, to give the octahydroquinoline 10. Functional group manipulation converted 10 into the Clavelina alkaloid ( + )-Lepadin B 11. The construction of trisubstituted alkenes by ring-closing metathesis can be difficult, and medium rings with their transannular strain are notoriously challenging to form. Nevertheless, Karl-Heinz Altmann of the ETH Zürich was able (Angew. Chem. Int. Ed. 2008, 47, 10081), using the H2 catalyst, to cyclize 12 to cyclononene 13, the precursor to the Xenia lactone ( + )-Blumiolide C 14. It is noteworthy that these fi ve syntheses used four different metathesis catalysts in the key alkene forming step. For the cyclization of 7, the use of the Grubbs first generation catalyst G1, that couples terminal alkenes but tends not to interact with internal alkenes, was probably critical to success.
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6

Taber, Douglass F. "The Smith Synthesis of (−)-Calyciphylline N." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0095.

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The Daphniphyllum alkaloids are a diverse group, some of which exhibit potent bio­logical activity. Amos B. Smith III of the University of Pennsylvania envisioned (J. Am. Chem. Soc. 2014, 136, 870) the preparation of the bicyclo[2.2.2] core of (−)-calyciphylline N 3 by the intramolecular Diels–Alder cyclization of 1 to 2, with the silicon of 2 a surrogate for the secondary alcohol of 3. Following the precedent of Mori (Tetrahedron Asymm. 2005, 16, 685), the requi­site secondary center of 1 was set by methylation of the anion derived from the Evans acyl oxazolidinone 4. Reductive removal of the oxazolidinone led to the alcohol 5, that was reduced under Birch conditions, then isomerized with base to the desired conjugated diene 6. This was silylated with the alkenyl silane 7 to give the triene 1. Direct thermal cyclization of 1 gave a mixture of all four possible diastereomers of the cycloadduct. Fortunately, the Lewis acid-activated cyclization delivered 2 as the dominant diastereomer. To differentiate the two ends of the alkene, the ester of 2 was extended to the alco­hol 8. Epoxidation occurred from the more open face of the alkene, setting the stage for intramolecular opening and oxidation to give 9. Reduction with SmI2 and protec­tion then completed the preparation of the ketone 10. The third quaternary center of 3 was constructed by acetylation of 10 followed by Pd-catalyzed allylation, to give 11. On exposure to LDA, the derived iodide 12 smoothly cyclized to the cycloheptanone 13, the structure of which was confirmed by X-ray analysis. The alkene of 13 was converted to the primary alcohol, which was protected. The aryl lithium 14 then was used to selectively open the cyclic silyl ether, to give 15. Coupling with phthalimide followed by carbonylative vinylation of the derived vinyl triflate delivered the dienone 16. Exposure to HBF4 effected the desired Nazarov cyclization, and at the same time converted the aryl silane to the fluorosilane, set for the Tamao oxidation that revealed the secondary alcohol. The two alcohols were sequentially protected to give 17. Direct oxidation of the primary silyl ether gave the aldehyde.
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