Relevant bibliographies by topics / Transannular reaction

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  2. Dissertations / Theses
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Academic literature on the topic 'Transannular reaction'

Author: Grafiati
Published: 5 June 2025
Last updated: 1 August 2025

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Journal articles on the topic "Transannular reaction"

1

Frank, Scott A., Andrea B. Works, and William R. Roush. "Studies on the synthesis of the decahydro-as-indacene ring system of (-)-spinosyn A via transannular Diels-Alder reactions of substituted (E,E,E)-cyclododeca-1,6,8-trienes." Canadian Journal of Chemistry 78, no. 6 (2000): 757–71. http://dx.doi.org/10.1139/v00-045.

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Stereoselective syntheses of decahydro-as-indacenes 31 and 54 are reported. The key features of our syntheses of 31 and 54 are the tandem Ireland-Claisen ring contraction of lactones 29 and 38 followed by the transannular Diels-Alder cyclization of cyclododecatrienes 30 and 35. Transition state modeling of both the transannular Diels-Alder reaction and the Ireland-Claisen ring contraction using PCModel is also described.Key words: transannular Diels-Alder reactions, tandem reactions, Claisen ring contraction, Spinosyn A, synthetic study.
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Marinier, Anne, Kurt Baettig, Carol Dallaire, Rita Pitteloud, and Pierre Deslongchamps. "Synthesis and transannular Diels–Alder reaction of a cis–trans–trans and a trans–cis–cis 13-membered macrocyclic trienone." Canadian Journal of Chemistry 67, no. 10 (1989): 1609–17. http://dx.doi.org/10.1139/v89-246.

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The synthesis of the cis–trans–trans5 and trans–cis–cis6 macrocyclic trienones from cyclohexene is described. Upon heating at 300 °C, trienone 5 underwent 1,5-H shift and transannular Diels–Alder reaction to give adducts 33, 34, and 35 while trienone 6 provided tricyclic ketone 37. Keywords: transannular Diels–Alder reaction.
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Beaubien, Sylvie, та Pierre Deslongchamps. "Total synthesis of 14β-fluorosteroids via a transannular Diels–Alder reaction". Canadian Journal of Chemistry 84, № 1 (2006): 29–48. http://dx.doi.org/10.1139/v05-259.

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14β-Fluorosteroids 3 and 4 were synthesized to give a new class of unnatural cardenolides. The total synthesis of racemic 14β-fluorosteroids was accomplished using a highly diastereoselective transannular Diels–Alder reaction on a trans-cis-cis macrocyclic triene. The α-fluoro analog 4 provided a comparable inhibitory activity to natural digitoxigenin 1.Key words: fluorosteroid, bioisostere, cardiovascular diseases, transannular Diels–Alder reaction (TADA), macrocyclization.
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Xu, Yao-Chang, Andrew L. Roughton, Raymond Plante, Solo Goldstein, and Pierre Deslongchamps. "Stereocontrolled construction of 1,7-dimethyl A.B.C.[6.6.6] tricycles. Part I. Transannular Diels–Alder reactions of 14-membered macrocycles containing trans-dienophiles." Canadian Journal of Chemistry 71, no. 8 (1993): 1152–68. http://dx.doi.org/10.1139/v93-152.

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Transannular Diels–Alder reactions of 14-membered macrocyclic trienes possessing a methyl substituent on both the diene and dienophile moiety have been investigated. Macrocyclic structures 1a, 1b, and 1c having cis-trans-trans (CTT), trans-cis-trans (TCT), and trans-trans-trans (TTT) geometries could be stereoselectively constructed by coupling appropriately functionalized dienes 5 and dienophile 4 following an intramolecular displacement of an allylic halide by the anion of an appropriately located dimethyl malonate unit. The transannular Diels–Alder reaction performed on 1a led to a mixture
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Bérubé, Gervais, and Pierre Deslongchamps. "Synthesis and transannular Diels–Alder reaction of a 13-membered macrocyclic triene having a tetrasubstituted enol ether as dienophile." Canadian Journal of Chemistry 68, no. 3 (1990): 404–11. http://dx.doi.org/10.1139/v90-062.

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The syntheses of the acyclic triene trans–trans–cis27 and trans–trans–trans31 are described. Macrocyclization and concomitant transannular Diels–Alder reaction were performed with the chloride derivative obtained from the trans–trans–cis triene alcohol 27 yielding a mixture of the tricyclic compounds trans–syn–trans33 and cis–syn–cis34. On the other hand, macrocyclization of the chloride derived from trans–trans–trans triene 31 was not successful. Keywords: transannular process, Diels–Alder reaction, macrocyclic triene, macrocyclization, tricyclic compounds, organic synthesis.
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Kasal, Alexander, та Jaroslav Zajíček. "Spontaneous transannular reaction in Δ9-unsaturated A-homo-B,19-dinorsteroids". Collection of Czechoslovak Chemical Communications 54, № 5 (1989): 1327–35. http://dx.doi.org/10.1135/cccc19891327.

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The epoxidation of 3β-hydroxy derivatives of Δ9-unsaturated A-homo-B,19-dinorsteroids (type I-IV) proceeds with spontaneous participation of the 3β-hydroxyl under formation of transannular 9α-hydroxy-3β,10β-oxides IX, X, XV and XVII. Epoxidation of the corresponding esters V-VIII affords predominantly 9α,10α-epoxides XIV, XVI, XVIII and XIX which, after hydrolysis of the ester groups are also converted into the transannular 3β,10β-oxides of the type IX.
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Mato, Raquel, Efraim Reyes, Luisa Carrillo, et al. "Catalytic enantioselective domino Michael/transannular aldol reaction under bifunctional catalysis." Chemical Communications 56, no. 86 (2020): 13149–52. http://dx.doi.org/10.1039/d0cc05981a.

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8

Cantin, Michel, Yao-Chang Xu, and Pierre Deslongchamps. "Stereocontrolled construction of A.B.C.[6.6.6] tricycle via transannular Diels–Alder reaction of 14-membered triene macrocycle." Canadian Journal of Chemistry 68, no. 12 (1990): 2144–52. http://dx.doi.org/10.1139/v90-329.

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The synthesis of the four acyclic trienes 11a, b and 20a, b is reported. The tandem macrocyclization and stereoselective transannular Diels–Alder reaction of acyclic trienes 11b (trans-trans-cis) and 20b (trans-trans-trans) were observed in the presence of Cs2CO3 at 85 °C to give tricycles 30 (TST) and 32 (CAT) respectively. However, treatment of acyclic trienes 11a (cis-trans-cis) and 20a (cis-trans-trans) under the same conditions yielded the 14-membered macrocycles 21 and 23, which were stereoselectively transformed at 250 °C into tricycles 22 (CST) and 24 (CAT) respectively in excellent yi
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Mato, Raquel, Rubén Manzano, Efraim Reyes, Luisa Carrillo, Uxue Uria, and Jose L. Vicario. "Catalytic Enantioselective Transannular Morita–Baylis–Hillman Reaction." Journal of the American Chemical Society 141, no. 24 (2019): 9495–99. http://dx.doi.org/10.1021/jacs.9b03679.

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Chemler, Sherry R., and Samuel J. Danishefsky. "Transannular Macrocyclization via IntramolecularB-Alkyl Suzuki Reaction." Organic Letters 2, no. 17 (2000): 2695–98. http://dx.doi.org/10.1021/ol0062547.

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Dissertations / Theses on the topic "Transannular reaction"

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Conyers, Ryan C. "An Investigation of Gold(I) Catalyzed Cycloaddition Reactions." Miami University / OhioLINK, 2013. http://rave.ohiolink.edu/etdc/view?acc_num=miami1366197923.

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Craft, Derek T. "Palladium and Gold-Catalyzed transannular [4+3] cycloaddition reactions: Application to the ABCD carbon framework of Cortistatin A. A short synthesis of S-(+)-Siphonodiol. New chiral Au(I) N-heterocyclic carbene complexes and their use in intramolecular c." Oxford, Ohio : Miami University, 2010. http://rave.ohiolink.edu/etdc/view?acc%5Fnum=miami1272036117.

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Rajapaksa, Naomi Samadara. "I. Stereoselective Construction of Polycyclic Architectures: Enantioselective Catalytic Transannular Ketone-Ene Reactions and an Enantioselective Total Synthesis of (+)-Reserpine II. Synthesis of Chiral Bisthioureas for Anion-Abstraction Catalysis." Thesis, Harvard University, 2013. http://dissertations.umi.com/gsas.harvard:11127.

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The research presented herein explores three aspects of asymmetric catalysis: (1) the development of new catalytic enantioselective reactions, (2) the application of stereoselective catalysis to natural product total synthesis, and (3) the design and synthesis of new chiral catalysts.<br>Chemistry and Chemical Biology
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Bourcet, Emmanuel. "Application des réactions de métathèse en synthèse totale : approche synthètique vers les aurisides." Phd thesis, Université Claude Bernard - Lyon I, 2009. http://tel.archives-ouvertes.fr/tel-00694389.

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Les réactions de métathèse sont des méthodes performantes pour la création de doubles liaisons carbone-carbone et leurs popularités s'expliquent par l'accessibilité des catalyseurs nécessaires à celles-ci et par la facilité de mise en oeuvre de ces réactions. Elles ont par ailleurs trouvé de nombreuses applications dans la synthèse de molécules naturelles.Les aurisides A et B sont des molécules naturelles d'origine marine isolées du lièvre des mers Dolabella Auricularia en 1996. Ces macrolides présentent une activité cytotoxique intéressante contre des lignées de cellules cancéreuses HeLaS3 av
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Caramori, Giovanni Finoto. "Estudo computacional de [2.2]ciclofanos." Universidade de São Paulo, 2006. http://www.teses.usp.br/teses/disponiveis/59/59138/tde-20102006-053102/.

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Neste trabalho foram estudados computacionalmente os [2.2]ciclofanos ([2.2]paraciclofano (1), anti-[2.2]metaciclofano (2a), sin-[2.2]metaciclofano (2b) e [2.2]metaparaciclofano (3)), que são os [2n]ciclofanos mais simples, contendo dois anéis fenílicos conectados por duas pontes etilênicas. Os ciclofanos têm apresentado inúmeras aplicações importantes, podendo atuar como auxiliares em sínteses assimétricas e como catalisadores que simulam funções enzimáticas, apresentando seletividade em relação aos substratos. Eles são empregados tanto em químicab supramolecular quanto em áreas biomédicas. Es
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Xue, Haoran. "Toward the Total Synthesis of Norzoanthamine: The Development of a Transannular Michael Reaction Cascade." Thesis, 2013. http://hdl.handle.net/1969.1/149334.

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Norzoanthamine is a complex heptacyclic marine alkaloid isolated from colonial zoanthids. It potently inhibits loss of bone weight and strength in a postmenopausal osteoporosis mouse model, but its mode-of-action remains unknown. The scarcity of this natural product from its natural source and the need to access analogs for structure-activity relationship (SAR) study make it necessary to chemically synthesize this compound. However, the complex molecular skeleton, especially the highly functionalized and stereochemically complex ABC core structure of the natural product poses a significant cha
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Li, Jiang. "Cyclophanes, transannular inverse electron demand Diels-Alder reactions and a formal total synthesis of (±)-strychnine /." 2002.

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8

Li, Li Ping, and 黎麗萍. "Transannular reactions and electronic effects of polycyclic compounds." Thesis, 1994. http://ndltd.ncl.edu.tw/handle/53320310218756020603.

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Books on the topic "Transannular reaction"

1

Piet, Dennis P. Transannular cyclisation reactions of the germacrane system mediated by enzymes from Cichorium intybus. Landbouwuniversiteit Wageningen, 1996.

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2

Balskus, Emily Patricia. Asymmetric catalysis in the construction of complex molecules: A total synthesis of (+)-lactacystin and development of an enantioselective transannular Diels-Alder reaction. 2008.

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Book chapters on the topic "Transannular reaction"

1

Taber, Douglass. "The Roush Synthesis of ( + )-Superstolide A." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0093.

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( + )-Superstolide A 3, isolated from the New Caledonian sponge Neosiphonia superstes, shows interesting cytotoxicity against malignant cell lines at ~ 4 ng/mL concentration. The key transformation in the synthesis of 3 described (J. Am. Chem. Soc. 2008, 130, 2722) by William R. Roush of Scripps Florida was the transannular Diels-Alder cyclization of 2, which established, in one step with high diastereocontrol, both the cis decalin and the macrolactone of 3. The octaene 1 was assembled from four stereodefined fragments. The first, the linchpin 6, was prepared from the stannyl aldehyde 4. Homol
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2

Taber, Douglass F. "Tethered Diels-Alder Cycloaddition: (±)-Neovibsanin B (Imagawa, Nishizawa), Valerenic Acid (Mulzer), (-)-Himandrine (Movassaghi), (±)-Pallavicinolide A (Wong), (+)-Phomopsidin (Nakada)." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0077.

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It has generally been observed that prospective intramolecular Diels-Alder cycloadditions that would form a γ-lactone are reluctant to proceed. In the course of a synthesis of (±)-neovibsanin B 4, Hiroshi Imagawa and Mugio Nishizawa of Tokushima Bunri University reversed (Organic Lett. 2009, 11, 1253) the usual connectivity and found that the dienyl ester 1 could be induced to cyclize to 3. The solvent 2 improved both the yield and the diastereoselectivity of the cycloaddition. It was not surprising that Johann Mulzer of the University of Vienna could see (Organic Lett. 2009, 11, 1151) no evid
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Tanner, D., and E. Ascic. "5.11 Intramolecular and Transannular Diels–Alder Reactions." In Comprehensive Organic Synthesis II. Elsevier, 2014. http://dx.doi.org/10.1016/b978-0-08-097742-3.00512-7.

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Wang, X. W., Y. Wang, and J. Jia. "Enamine Catalysis of Intramolecular Transannular Aldol Reactions." In Lewis Base and Acid Catalysts. Georg Thieme Verlag KG, 2012. http://dx.doi.org/10.1055/sos-sd-204-00008.

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