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Journal articles on the topic 'Transannular reaction'

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Published: 5 June 2025
Last updated: 1 August 2025

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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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2

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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3

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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4

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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5

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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6

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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7

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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9

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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10

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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11

Chen, Peng, Liang Huo, Huilin Li, et al. "Bioinspired total synthesis of (−)-gymnothelignan L." Organic Chemistry Frontiers 5, no. 7 (2018): 1124–28. http://dx.doi.org/10.1039/c8qo00026c.

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The first asymmetric total synthesis of gymnothelignan L has been accomplished in 14 steps with 11.2% overall yield. The synthetic approach features an anti Evans aldol reaction, a diastereoselective methylation, a Suzuki–Miyaura coupling and a bioinspired desymmetric transannular Friedel–Crafts reaction.
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12

Xu, Yao-Chang, Andrew L. Roughton, Pierre Soucy, Solo Goldstein, and Pierre Deslongchamps. "Stereocontrolled construction of 1,7-dimethyl A.B.C.[6.6.6] tricycles. Part II. Transannular Diels–Alder reaction of 14-membered macrocycles containing cis-dienophiles." Canadian Journal of Chemistry 71, no. 8 (1993): 1169–83. http://dx.doi.org/10.1139/v93-153.

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The synthesis and transannular Diels–Alder reactions of 14-membered macrocyclic trienes containing a methyl-substituted diene and a methyl-substituted cis-dienophile moiety are described. As a result of the dienophile cis geometry the 1,7-dimethyl A.B.C.[6.6.6] tricycles obtained from the Diels–Alder reaction have a different stereochemistry at the four chiral centers than similar tricycles that were the subject of the preceding paper in this series. Thus trans-syn-cis (TSC) tricycle 30 was the sole product obtained from the trans-cis-cis (TCC) macrocycle 1b. In a similar fashion TCC macrocycl
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13

Xu, Yao-Chang, Michel Cantin, and Pierre Deslongchamps. "Stereocontrolled construction of A.B.C.[6.6.6] tricycle via transannular Diels–Alder reaction of 14-membered macrocycle with acetylene as dienophile." Canadian Journal of Chemistry 68, no. 12 (1990): 2137–43. http://dx.doi.org/10.1139/v90-328.

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The syntheses of the acyclic dienynes 14a (cis-trans-acetylene) and 14b (trans-trans-acetylene) are described. The tandem macrocyclization and transannular Diels–Alder reaction of the allylic chloride 14b was conducted in the presence of Cs2CO3 at 85 °C in one-pot to provide tricyclic product 16, with the two hydrogens in ring B being cis. On the other hand, treatment of the allylic chloride 14a under the same conditions afforded 14-membered macrocycle 17, which could be transformed at 250 °C into a similar tricyclic product 18 with the two hydrogens in ring B being trans, along with an intere
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14

Yan, Qiao, Patrick J. Carroll, Michael R. Gau, Jeffrey D. Winkler, and Madeleine M. Joullié. "A Transannular Rearrangement Reaction of a Pyrroloindoline Diketopiperazine." Organic Letters 21, no. 17 (2019): 6619–23. http://dx.doi.org/10.1021/acs.orglett.9b02084.

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15

Shimizu, Isao, and Hiroya Nakagawa. "Synthesis of (±)-Jasmine Ketolactone by transannular Michael reaction." Tetrahedron Letters 33, no. 34 (1992): 4957–58. http://dx.doi.org/10.1016/s0040-4039(00)61244-3.

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16

Xue, Haoran, Peddabuddi Gopal, and Jiong Yang. "Stereochemical Study of a Transannular Michael Reaction Cascade." Journal of Organic Chemistry 77, no. 20 (2012): 8933–45. http://dx.doi.org/10.1021/jo301287z.

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17

Balskus, E. P., and E. N. Jacobsen. "Asymmetric Catalysis of the Transannular Diels-Alder Reaction." Science 317, no. 5845 (2007): 1736–40. http://dx.doi.org/10.1126/science.1146939.

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18

Karabiyikoglu, Sedef, Byron A. Boon, and Craig A. Merlic. "Cycloaddition Reactions of Cobalt-Complexed Macrocyclic Alkynes: The Transannular Pauson–Khand Reaction." Journal of Organic Chemistry 82, no. 15 (2017): 7732–44. http://dx.doi.org/10.1021/acs.joc.7b01369.

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19

Hall, Dennis G., Renate Müller, and Pierre Deslongchamps. "Studies on the transannular Diels–Alder reaction of 15-membered macrocyclic trienes containing a trans-trans diene. Part II: Evidence for unsymmetrical transition states in the formation of A.B.C.[6.6.7] tricyclic products." Canadian Journal of Chemistry 73, no. 10 (1995): 1695–710. http://dx.doi.org/10.1139/v95-208.

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In the preceding paper (Part I) we described the preparation of 10 model TTT and TTC cyclopentadecatrienes. Their conversion to A.B.C.[6.6.7] tricyclic products via a transannular Diels–Alder (TADA) reaction and the analysis of the resulting diastereoselection along with proofs of structures are described in the present article (Part II). The required temperature of reaction was significantly higher (~100 °C) in comparison to that required for the 14-membered lower homologs, indicating that proximity effects are playing a key role in the TADA reaction. The presence of ester groups in the chain
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20

Chantigny, Yves A., Yves L. Dory, András Toró, and Pierre Deslongchamps. "Use of the transannular Diels–Alder (TADA) reaction to probe biological receptors: Rational design and synthesis of tricyclic TADA adducts capable of rigidly holding pharmacophore parts." Canadian Journal of Chemistry 80, no. 8 (2002): 875–84. http://dx.doi.org/10.1139/v02-064.

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Transannular Diels–Alder (TADA) adducts constitute a collection of rigid structures, whose conformational diversity is rich. It is possible to design such specifically functionalized molecules capable of binding to known biological targets by molecular modelling MCSS–HOOK (multiple copy simultaneous search). Here we show that such carefully designed compounds can be easily built from small synthons. TADA adducts are very interesting due to their huge conformational diversity, their rigidity (biological interest), and their ease of synthesis (chemical interest).Key words: tricycles, synthesis,
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21

C., A. M. A. Huq, and Sivakumar S. "One-pot synthesis of novel heterocyclic compounds via tandem reactions." Journal of Indian Chemical Society Vol. 91, Feb 2014 (2014): 313–17. https://doi.org/10.5281/zenodo.5749168.

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Post Graduate and Research Department of Chemistry, The New College, Affiliated to the University of Madras, Chennai-600 014, India <em>E-mail</em> : drmdabdulhuq@yahoo.com <em>Manuscript received 19 September 2012, revised 04 February 2013, accepted 07 May 2013</em> Novel heterocyclic compounds (2), (4) and (6) have been prepared by a tandem oxy-Cope rearrangement/S<sub>N</sub> displacement reaction, a tandem dianionic oxy-Cope rearrangement/nucleophilic substitution at carbonyl carbon and a tandem anionic oxy-Cope rearrangement/transannular reaction respectively. The oxy-Cope rearrangement i
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22

Hall, Dennis G., Renate Müller, and Pierre Deslongchamps. "Studies on the transannular Diels–Alder reaction of 15-membered macrocyclic trienes containing a trans-trans diene. Part I: Synthesis and isomerization of various model cyclopentadecatrienes." Canadian Journal of Chemistry 73, no. 10 (1995): 1675–94. http://dx.doi.org/10.1139/v95-207.

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The transannular Diels–Alder reaction of 15-membered macrocyclic trienes with a trans-trans-cis (TTC) olefin geometry can lead to A.B.C.[6.6.7] tricyclic products of trans-syn-trans (TST) and cis-syn-cis (CSC) stereochemistry whereas the TTT isomers can produce the trans-anti-cis (TAC) and cis-anti-trans (CAT) tricycles. In order to study the influence of the position (pro-6.6 or pro-6.7) and the nature (alkyl, alkoxymethyl, or formyl) of the dienophile substituent, a set of 10 model cyclopentadecatrienes was prepared. The synthesis of appropriately functionalized trisubstituted dienophile and
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23

Ndibwami, Alexis, Serge Lamothe, Daniel Guay, et al. "Transannular Diels–Alder reactions on 14-membered macrocyclic trienes. Part I: stereoselective syntheses of the macrocyclic trienes precursors." Canadian Journal of Chemistry 71, no. 5 (1993): 695–713. http://dx.doi.org/10.1139/v93-094.

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Transannular Diels–Alder reactions on 14-membered macrocycles containing properly located diene and methyl-substituted dienophile units lead to A.B.C.[6.6.6] tricycles related to steroids. To study the influence of the olefin and diene geometry on the stereochemical outcome of the Diels–Alder reaction it was necessary to prepare macrocyclic trienes of well-defined stereochemistry. Eight different types of macrocyclic trienes might be obtained by the coupling of appropriate dienophiles and dienes, namely, TTC, TTT, TCC, TCT, CTC, CTT, CCC, and CCT. In this paper (first in a series of two), the
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24

Schläpfer-Dähler, Marlise, Roland Prewo, Jost H. Bieri, Gabriel Germain, and Heinz Heimgartner. "Bildung eines Azacyclols durch transanulare Ringkontraktion." CHIMIA 42, no. 1 (1988): 25. https://doi.org/10.2533/chimia.1988.25.

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Reaction of 3-dimethylamino-2,2-dimethyl-2H-azirine (1) with phthalimide (8) in polar solvents yields the (1:1)-adduct 2-dimethylamino-9b-hydroxy-3,3-dimethyl-5,9b-dihydro-3H-imidazo[2,1-a]isoindol-5-one (10). The structure of this azacyclol has been established by X-ray crystallography. A reaction mechanism via ring expansion to an eight-membered heterocycle followed by transannular ring contraction explains the formation of 10.
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25

Ohkura, Kazue, and Koh-ichi Seki. "Photoinduced Transannular Reaction of 1,3-Dimethyl-Cyclooctapyrimidine-2,4-Diones¶." Photochemistry and Photobiology 75, no. 6 (2007): 579–84. http://dx.doi.org/10.1562/0031-8655(2002)0750579ptrodc2.0.co2.

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26

Ohkura, Kazue, and Koh-ichi Seki. "Photoinduced Transannular Reaction of 1,3-Dimethyl-Cyclooctapyrimidine-2,4-Diones¶." Photochemistry and Photobiology 75, no. 6 (2002): 579. http://dx.doi.org/10.1562/0031-8655(2002)075<0579:ptrodc>2.0.co;2.

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27

Phoenix, Serge, Maddi Sridhar Reddy, and Pierre Deslongchamps. "Total Synthesis of (+)-Cassaine via Transannular Diels−Alder Reaction." Journal of the American Chemical Society 130, no. 42 (2008): 13989–95. http://dx.doi.org/10.1021/ja805097s.

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28

Warrington, Jeffrey M., Glenn P. A. Yap, and Louis Barriault. "Tandem Oxy-Cope/Transannular Ene Reaction of 1,2-Divinylcyclohexanols." Organic Letters 2, no. 5 (2000): 663–65. http://dx.doi.org/10.1021/ol005502w.

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29

Longobardi, Lauren E., Tayseer Mahdi, and Douglas W. Stephan. "B(C6F5)3 mediated arene hydrogenation/transannulation of para-methoxyanilines." Dalton Transactions 44, no. 16 (2015): 7114–17. http://dx.doi.org/10.1039/c5dt00921a.

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The stoichiometric reaction of para-methoxyanilines and B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub> under H<sub>2</sub> results in reduction of the N-bound phenyl ring(s), and subsequent transannular ring closure with elimination of methanol, affording the respective 7-azabicyclo[2.2.1]heptane derivatives.
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30

Shimizu, Tomoe, Katsuhiko Hida, and Takehiko Yamato. "Synthesis of 5-tert-butyl-8,12,14-trimethyl- and 5-tert-butyl-8,12,14,16-tetramethyl[2.2]metacyclophane and their treatment with Lewis acids in benzene." Journal of Chemical Research 2009, no. 7 (2009): 443–47. http://dx.doi.org/10.3184/030823409x465222.

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Treatment of 5- tert-butyl-8,12,14,16-tetramethyl[2.2]MCP with AlCl3-MeNO2 in benzene led to trans- tert-butylation to afford 8,12,14,16-tetramethyl[2.2]MCP in good yield along with tert-butylbenzene. On the other hand, the same treatment of 5- tert-butyl-8,12,14-trimethyl[2.2]MCP led to transannular cyclisation reaction and isomerisation reaction to afford the corresponding strainless 2- tert-butyl-3a,6,8-trimethyl-3,3a,4,5,9,10-hexahydropyrene in good yield.
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31

Marinier, Anne, and Pierre Deslongchamps. "Stereocontrolled chiral synthesis of a trans-anti-trans tricycle by a transannular Diels–Alder reaction." Canadian Journal of Chemistry 70, no. 9 (1992): 2350–64. http://dx.doi.org/10.1139/v92-297.

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The racemic and chiral synthesis of trans-cis-cis macrocyclic triene 5 is described. Heating this compound at 262 °C leads via a transannular Diels–Alder reaction to the tricyclic structure 6, which can be further transformed into tricyclic compound 7. This work constitutes a preliminary study for the synthesis of corticoids.
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32

Pedrón, Manuel, Jana Sendra, Irene Ginés, Tomás Tejero, Jose L. Vicario, and Pedro Merino. "Computational studies of Brønsted acid-catalyzed transannular cycloadditions of cycloalkenone hydrazones." Beilstein Journal of Organic Chemistry 19 (April 20, 2023): 477–86. http://dx.doi.org/10.3762/bjoc.19.37.

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The contribution to the energy barrier of a series of tethers in transannular cycloadditions of cycloalkenes with hydrazones has been computationally studied by using DFT. The Houk's distortion model has been employed to evaluate the influence of the tether in the cycloaddition reaction. That model has been extended to determine the contribution of each tether and, more importantly, the effect exerted between them. In addition to the distortion induced by the tethers, the entropy effects caused by them has also been studied. The analysis of the evolution of the electron localization function a
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33

Du, Rui Huan, Bai Qin Zheng, and Jian Min Zhang. "Theoretical Study of the Diels-Alder Reaction in the Synthesis of Abietane Diterpenes." Applied Mechanics and Materials 608-609 (October 2014): 981–84. http://dx.doi.org/10.4028/www.scientific.net/amm.608-609.981.

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Density Functional Theory (DFT),at the B3LYP/6-311 G(d,p) level of theory and Moller-Plesse Theory (MP2/6-311G (d,p)) has been performed to study the mechanism, potential energy surface of the Diels-Alder reaction in the Synthesis of abietane diterpenes. The obtained results indicate that the reaction is concerted and synchronous processes. The transannular product is formed via a six-member ring transition state; yield of the endo product is higher. And finally, the enthalpie and activation energie of the reaction are given respectively. The reaction is exothermic,which accords well with expe
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34

Aly, Ashraf A., Alaa A. Hassan, and Aboul-Fetouh E. Mourad. "Novel [2.2]paracyclophane derivatives via charge-transfer complexation." Canadian Journal of Chemistry 71, no. 11 (1993): 1845–49. http://dx.doi.org/10.1139/v93-231.

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The transannular electronic interactions in [2.2]paracyclophanes affect the selectivity of the tricyanovinylation reaction with tetracyanoethylene (TCNE). In addition to the normal N-tricyanovinyl product, 4-amino[2,2]paracyclophane reacts with TCNE to give oxaziridine derivatives. In the case of reaction with 4-N-methylamino[2.2]paracyclophane, the unusual N-tricyanovinylated product as well as 4-(N-carbonitrile-N-methyl)annino[2.2]paracyclophane was isolated. The reaction of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) with 4-amino[2.2]paracyclophane results in formation of 2-cyano-3-(4-[
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35

Wolfe, Saul, Anthony V. Buckley, and Noham Weinberg. "A comprehensive computational examination of transannular Diels–Alder reactions of unsubstituted C14 trienes — Barriers, template effects, and the Curtin–Hammett principle." Canadian Journal of Chemistry 79, no. 8 (2001): 1284–92. http://dx.doi.org/10.1139/v01-103.

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A combination of MM3-level molecular mechanics calculations and PM3-level semiempirical molecular orbital calculations has been employed, in conjunction with an algorithm for the comprehensive conformational analysis of cyclic compounds, to obtain 1202 unique 1,3,9-cyclotetradecatriene conformations, distributed over the six possible geometrical isomers, and 70 unique transannular Diels–Alder transition structures leading to the six possible stereoisomeric tricyclic olefins. A kinetic analysis that takes into account all minima of a given geometrical isomer and all transition structures leadin
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36

Kräme, Guido, Annette Oehlhof, and Herbert Meier. "Equilibrium between Hydroxycycloalkanones and Oxabicycloalkanols." Zeitschrift für Naturforschung B 64, no. 7 (2009): 847–50. http://dx.doi.org/10.1515/znb-2009-0713.

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Hydroxycycloalkanones 1 of medium ring size (8 -10) exist in a transannular tautomeric equilibrium with the corresponding oxabicycloalkan-1-ols 2, which represent hemiacetals. Normally, the bicyclic structures 2 predominate in solution although their portion decreases with increasing solvent polarity. A correlation of the Gibbs reaction enthalpies ΔG (1→2) with the solvent parameters ET (30) is presented.
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37

Han, Chong, Sathish Rangarajan, Alicia C. Voukides, Aaron B. Beeler, Richard Johnson, and John A. Porco. "Reaction Discovery Employing Macrocycles: Transannular Cyclizations of Macrocyclic Bis-lactams." Organic Letters 11, no. 2 (2009): 413–16. http://dx.doi.org/10.1021/ol802729f.

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38

Padrón, Juan I., Jesús T. Vázquez, Ezequiel Q. Morales, Miguel Zárraga, and Julio D. Martín. "Conformationally controlled transannular reaction of a 12-membered macrocyclic trienol." Tetrahedron: Asymmetry 3, no. 3 (1992): 415–30. http://dx.doi.org/10.1016/s0957-4166(00)80285-2.

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39

Snider, Barry B., and Jingye Zhou. "Synthesis of (+)-Sch 642305 by a Biomimetic Transannular Michael Reaction." Organic Letters 8, no. 7 (2006): 1283–86. http://dx.doi.org/10.1021/ol052948+.

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40

Chemler, Sherry R., and Samuel J. Danishefsky. "ChemInform Abstract: Transannular Macrocyclization via Intramolecular B-Alkyl Suzuki Reaction." ChemInform 31, no. 47 (2000): no. http://dx.doi.org/10.1002/chin.200047052.

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41

Ndibwami, Alexis, Serge Lamothe, Pierre Soucy, Solo Goldstein, and Pierre Deslongchamps. "Transannular Diels–Alder reactions on 14-membered macrocyclic trienes. Part II: formation of macrocycles and thermal conversion into tricyclic systems." Canadian Journal of Chemistry 71, no. 5 (1993): 714–25. http://dx.doi.org/10.1139/v93-095.

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In the preceding paper (Part I) we described the synthesis of eight isomeric acyclic trienes. These compounds could be transformed into the corresponding macrocyclic trienes, which were further converted into tricyclic A.B.C.[6.6.6] products by a thermal transannular Diels–Alder reaction. The experimental results of this study and their analysis are reported in the present paper. The comparison with theoretical predictions is also discussed.
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42

Kim, Hyoungsu, Hosam Choi, and Kiyoun Lee. "A Concise Total Synthesis of (±)-Mesembrine." Synlett 29, no. 09 (2018): 1203–6. http://dx.doi.org/10.1055/s-0036-1591547.

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A concise total synthesis of (±)-mesembrine has been successfully accomplished in seven steps and 24% overall yield from commercially available 3-ethoxy-2-cyclohexen-1-one. Central to the assembly of the skeleton of mesembrine are a Johnson–Claisen rearrangement for the formation of the benzylic quaternary stereocenter and direct allylic oxidation to generate the substrate for the amidation/transannular aza-conjugate addition reaction.
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43

Kuroyanagi, Masanori, Osamu Shirota, Setsuko Sekita, and Takahisa Nakane. "Transannular Cyclization of (4S,5S)-Germacrone-4,5-epoxide into Guaiane and Secoguaiane-type Sesquiterpenes." Natural Product Communications 7, no. 4 (2012): 1934578X1200700. http://dx.doi.org/10.1177/1934578x1200700406.

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Germacrone (1) and ( 4S,5S)-germacrone-4,5-epoxide (2) were isolated, along with guaiane and secoguaiane-type sesquiterpenes, from Curcuma aromatica plants. Compound 2 was derived from 1 and cyclized through transannular (T-A) reactions into various guaiane and secoguaiane-type sesquiterpenes in C. aromatica. The cyclization reaction of 2 was initiated by protonation at an epoxide oxygen atom, followed by cleavage of the epoxide ring and the formation of a C-C bond between C-1 and C-5 to give guaiane-type derivatives. Acidic and thermal treatments of 2 produced twelve sesquiterpenes having gua
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44

HORIKAWA, Tamaki, Yoshihiko NORIMINE, Masakazu TANAKA, Kiyoshi SAKAI, and Hiroshi SUEMUNE. "Synthesis of Optically Active Bicyclo(3.3.0)octane Skeleton Using Transannular Reaction." CHEMICAL & PHARMACEUTICAL BULLETIN 46, no. 1 (1998): 17–21. http://dx.doi.org/10.1248/cpb.46.17.

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45

Warrington, Jeffrey M., Glenn P. A. Yap, and Louis Barriault. "ChemInform Abstract: Tandem Oxy-Cope/Transannular Ene Reaction of 1,2-Divinylcyclohexanols." ChemInform 31, no. 24 (2010): no. http://dx.doi.org/10.1002/chin.200024102.

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46

Kliegel, Wolfgang, Gottfried Lubkowitz, Steven J. Rettig, and James Trotter. "Structural studies of organoboron compounds LIX. Reaction of two sterically hindered N,N′-dihydroxyaminals with phenylboronic acid, and the crystal and molecular structures of the resulting 1,3,5-trioxa-6,8-diaza-2,4-diboracyclooctanes and one of the adducts." Canadian Journal of Chemistry 71, no. 12 (1993): 2129–38. http://dx.doi.org/10.1139/v93-264.

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The syntheses of the sterically hindered N,N′-dihydroxyaminals; N,N′-bis(1-ethoxycarbonyl-1-methylethyl)-N,N′-dihydroxymethanediamine, 1b, and N,N′-bis(1,1-dimethylethyl)-N,N′-dihydroxymethanediamine, 1c, and their reactions with phenylboronic acid to yield the 1,3,5-trioxa-6,8-diaza-2,4-diboracyclooctanes 3 and 4, respectively, are described. Crystals of 1b are tetragonal, a = 18.413(1), c = 9.867(2) Å, Z = 8, space group I41; those of 3 are monoclinic, a = 20.420(4), b = 8.272(4), c = 17.851(5) Å, β = 117.34(1)°, Z = 4, space group C2/c; and those of 4 are monoclinic, a = 9.493(4), b = 16.20
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47

Yamato, Takehiko, Koji Fujita, Keigo Futatsuki, and Hirohisa Tsuzuki. "Medium-sized cyclophanes. Part 53.1 Synthesis and conformational studies, and photoinduced cyclization of syn-[n.2]metacyclophanenes." Canadian Journal of Chemistry 78, no. 8 (2000): 1089–99. http://dx.doi.org/10.1139/v00-110.

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A series of [n.2]metacyclophanenes (3) and (6) were prepared in good yields by a McMurry cyclization of 1,n-bis(3-acetyl-4-methoxyphenyl)alkanes (2) and 1,3-bis(3-formyl-4-methoxyphenyl)propane (5), respectively. Compounds 3b, 3c exist in the syn-conformation due to the steric repulsion between the methyl groups at the ethano bridge and the methoxy groups at the aromatic rings while compound 6 prefers the anti-conformation typical of [3.2]metacyclophanes. The assignment of syn-conformations has been confirmed by 1H NMR analyses and X-ray diffraction studies. Photoinduced transannular cyclizati
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48

Kollenz, Gert, and Curt Wentrup. "From dipivaloylketene to tetraoxaadamantanes." Beilstein Journal of Organic Chemistry 14 (January 2, 2018): 1–10. http://dx.doi.org/10.3762/bjoc.14.1.

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Dipivaloylketene (2) is obtained by flash vacuum pyrolysis of furan-2,3-dione 6 and dimerizes to 1,3-dioxin-4-one 3, which is a stable but reactive ketene. The transannular addition and rearrangement of enols formed by the addition of nucleophiles to the ketene function in 3 generates axially chiral 2,6,9-trioxabicyclo[3.3.1]nonadienes (bisdioxines) 4. When arylamines are used as the nucleophiles under neutral conditions, decarboxylation occurs during the formation of bisdioxines 8. However, when water or alcohols are added to 3 under acidic conditions, bisdioxine-carboxylic acids and esters 1
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49

Mato, Raquel, Rubén Manzano, Efraím Reyes, et al. "Kinetic Resolution in Transannular Morita-Baylis-Hillman Reaction: An Approximation to the Synthesis of Sesquiterpenes from Guaiane Family." Catalysts 12, no. 1 (2022): 67. http://dx.doi.org/10.3390/catal12010067.

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An approximation to the synthesis of several sesquiterpenes from the Guaiane family is described in which the core structure was obtained through a transannular Morita-Baylis-Hillman reaction performed under kinetic resolution. Several manipulations of the obtained MBH adduct have been carried out directed towards the total synthesis of γ-Gurjunene, to the formal synthesis of Clavukerin A, to the synthesis of a non-natural isomer of isoguaiane and to the synthesis of an advanced intermediate in the total synthesis of Palustrol.
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50

Camps, Pelayo, Diana Görbig, Victoria Muñoz-Torrero, and Francesc Pérez. "Synthesis, Conformational Analysis and Transannular Reactions of 5,9-Propanobenzo[7]annulene Derivatives." Collection of Czechoslovak Chemical Communications 62, no. 10 (1997): 1585–98. http://dx.doi.org/10.1135/cccc19971585.

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(5α,9α,11β)-11-Hydroxy-6,7,8,9-tetrahydro-5H-5,9-propanobenzo[7]annulen-7-one ethylene ketal (6a) and its 11α-methyl derivative (6b) were prepared from monoketal 3. These compounds underwent acid-catalyzed transannular reactions leading to 6,7,8,9-tetrahydro-5H-5,9-propanobenzo[7]annulene derivatives 5a, 8a and 5b, 8b, respectively, depending on the reaction conditions. The compounds 6a and 6b were dehydrated to 6,7,8,9-tetrahydro-5H-5,9-prop[1]enobenzo[7]annulen-7-one (9a) and its 11-methyl derivative (9b), respectively. The conformational analysis of the 5,9-propanobenzo[7]annulene derivativ
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