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Journal articles on the topic 'Transannular cyclizations'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Jahn, Ullrich, and Dennis P. Curran. "Towards a tandem-radical macrocyclization-transannular cyclization approach to steroids: Transannular cyclizations of a macrocyclic core." Tetrahedron Letters 36, no. 49 (December 1995): 8921–24. http://dx.doi.org/10.1016/0040-4039(95)01918-8.

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2

JAHN, U., and D. P. CURRAN. "ChemInform Abstract: Towards a Tandem-Radical Macrocyclization-Transannular Cyclization Approach to Steroids: Transannular Cyclizations of a Macrocyclic Core." ChemInform 27, no. 13 (August 12, 2010): no. http://dx.doi.org/10.1002/chin.199613100.

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3

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 (August 1, 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 cyclization of [n.2]metacyclophanenes (3) and (6) in the presence of iodine as an oxidant afforded phenanthrene-anellated polycyclic aromatic hydrocarbons. Apparently, the rate of the photocyclization of anti-6 was found to be much faster than that of syn-3b and almost completed within 1 h. Thus, the different reactivities for the irradiation of syn- and anti-conformer were observed. The reason for the present preference for the formation of trans-dihydrophenanthrene rather than cis-dihydrophenanthrene as the intermediate might be attributable to the more stable chair form transition state than boat one and the conformational fixation to the chair form in the ground and transition state is possible in the anti-conformer.Key words: cyclophanes, strained molecule, McMurry reaction, CC coupling, conformation analysis, cyclizations, photolysis, transannular reactions, transition states.

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4

Kende, Andrew S., Clara E. Mota Nelson, and Sébastien Fuchs. "Palladium-mediated transannular cyclizations of medium-ring olefinic enolsilanes." Tetrahedron Letters 46, no. 47 (November 2005): 8149–52. http://dx.doi.org/10.1016/j.tetlet.2005.09.125.

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5

Rychlet Elliott, Maryse, Anne-Lise Dhimane, and Max Malacria. "Biomimetic Diastereoselective Total Synthesis ofepi-Illudolviaa Transannular Radical Cyclizations Strategy." Journal of the American Chemical Society 119, no. 14 (April 1997): 3427–28. http://dx.doi.org/10.1021/ja970139i.

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6

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 (January 15, 2009): 413–16. http://dx.doi.org/10.1021/ol802729f.

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7

Williams, David R., and Paul J. Coleman. "Studies on the dolabellanes: Stereoselective transannular cyclizations of dolabelladiene macrocycles." Tetrahedron Letters 36, no. 1 (January 1995): 39–42. http://dx.doi.org/10.1016/0040-4039(94)02164-7.

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8

Curran, Dennis P., and Wang Shen. "Tandem transannular radical cyclizations. Total syntheses of (±)-modhephene and (±)-epi-modhephene." Tetrahedron 49, no. 4 (January 1993): 755–70. http://dx.doi.org/10.1016/s0040-4020(01)80321-5.

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9

HANDA, S., and G. PATTENDEN. "ChemInform Abstract: Free Radical-Mediated Macrocyclizations and Transannular Cyclizations in Synthesis." ChemInform 28, no. 37 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199737382.

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10

Doi, Takayuki, and Takashi Takahashi. "Syntheses and transannular cyclizations of neocarzinostatin-chromophore and esperamicin-calichemicin analogs." Journal of Organic Chemistry 56, no. 11 (May 1991): 3465–67. http://dx.doi.org/10.1021/jo00011a002.

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11

Rodríguez, Gema, Luis Castedo, Domingo Domínguez, and Carlos Saá. "Transannular cyclizations of 10-membered lactams: An easy route to isoquinoline alkaloids." Tetrahedron Letters 39, no. 36 (September 1998): 6551–54. http://dx.doi.org/10.1016/s0040-4039(98)01363-x.

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12

Marchand, Alan P., Benny E. Arney, Paritosh R. Dave, N. Satyanarayana, William H. Watson, and Ante Nagl. "Transannular cyclizations in the pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione system. A reinvestigation." Journal of Organic Chemistry 53, no. 11 (May 1988): 2644–47. http://dx.doi.org/10.1021/jo00246a053.

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13

WILLIAMS, D. R., and P. J. COLEMAN. "ChemInform Abstract: Studies on the Dolabellanes: Stereoselective Transannular Cyclizations of Dolabelladiene Macrocycles." ChemInform 26, no. 20 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199520176.

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14

Joshua, Alummoottil V., John R. Scott, Sham M. Sondhi, Richard G. Ball, and J. William Lown. "Transannular cyclizations of 1,2-dithia-5,8-diazacyclodeca-4,8-dienes during borohydride reduction." Journal of Organic Chemistry 52, no. 12 (June 1987): 2447–51. http://dx.doi.org/10.1021/jo00388a020.

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15

Murthy, Yerramilli V. S. N., and C. N. Pillai. "Transannular Cyclizations in Caged Bislactones: Synthesis of Polyfunctional Cyclopentanes and Oxa-Cage Compounds." Synthetic Communications 26, no. 12 (June 1996): 2363–81. http://dx.doi.org/10.1080/00397919608004548.

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16

Adio, Adewale M. "Germacrenes A–E and related compounds: thermal, photochemical and acid induced transannular cyclizations." Tetrahedron 65, no. 8 (February 2009): 1533–52. http://dx.doi.org/10.1016/j.tet.2008.11.050.

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17

CURRAN, D. P., and W. SHEN. "ChemInform Abstract: Tandem Transannular Radical Cyclizations. Total Syntheses of (.+-.)- Modhephene and (.+-.)-Epi-Modhephene." ChemInform 24, no. 19 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199319230.

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18

Nobusue, Shunpei, Ayumi Yoshizaki, Masahito Miki, Hirokazu Miyoshi, Akihiro Shimizu, and Yoshito Tobe. "Transformation of octadehydrodibenzo[12]annulene to benzonaphthopentalene by successive nucleophilic and electrophilic transannular cyclizations." Tetrahedron 70, no. 45 (November 2014): 8474–79. http://dx.doi.org/10.1016/j.tet.2014.09.079.

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19

Edstrom, Eric D. "An unexpected reversal in the stereochemistry of transannular cyclizations. A stereoselective synthesis of (±)-epilupinine." Tetrahedron Letters 32, no. 41 (October 1991): 5709–12. http://dx.doi.org/10.1016/s0040-4039(00)93536-6.

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20

Leeson, Paul D., Kim James, Robert W. Carling, Kevin W. Moore, Julian D. Smith, Akbar A. Mahomed, Richard H. Herbert, and Raymond Baker. "Transannular cyclizations of 5-(hydroxyamino)dibenzo[a,e]cyclooctatrienes. Regioselective synthesis of dibenzohomotropane analogs." Journal of Organic Chemistry 55, no. 7 (March 1990): 2094–103. http://dx.doi.org/10.1021/jo00294a023.

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21

RODRIGUEZ, G., CASTEDO L. CASTEDO. L., D. DOMINGUEZ, and C. SAA. "ChemInform Abstract: Transannular Cyclizations of 10-Membered Lactams: An Easy Route to Isoquinoline Alkaloids." ChemInform 29, no. 48 (June 18, 2010): no. http://dx.doi.org/10.1002/chin.199848172.

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22

Newcomb, Martin, and Donald J. Marquardt. "N-Hydroxypyridine-2-thione Carbamates as Aminiun Radical Cation Precursors. Transannular Radical Cyclizations Forming Tropanes." HETEROCYCLES 28, no. 1 (1989): 129. http://dx.doi.org/10.3987/com-88-s52.

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23

Colclough, David, James B. White, William B. Smith, and Yongliang Chu. "Electrophilic and radical transannular cyclizations of 5-cyclodecenone to give either hydronaphthalene or hydroazulene products." Journal of Organic Chemistry 58, no. 23 (November 1993): 6303–13. http://dx.doi.org/10.1021/jo00075a025.

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24

MURTHY, Y. V. S. N., and C. N. PILLAI. "ChemInform Abstract: Transannular Cyclizations in Caged Bislactones: Synthesis of Polyfunctional Cyclopentanes and Oxa-Cage Compounds." ChemInform 27, no. 36 (August 5, 2010): no. http://dx.doi.org/10.1002/chin.199636175.

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25

Winkler, Jeffrey D., and V. Sridar. "Stereochemical control of transannular radical cyclizations. A new approach to the synthesis of linearly fused cyclopentanoids." Journal of the American Chemical Society 108, no. 7 (April 1986): 1708–9. http://dx.doi.org/10.1021/ja00267a061.

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26

Pérez Morales, M. Carmen, Julieta V. Catalán, Victoriano Domingo, Martín Jaraíz, M. Mar Herrador, José F. Quílez del Moral, José-Luis López-Pérez, and Alejandro F. Barrero. "Structural Diversity from the Transannular Cyclizations of Natural Germacrone and Epoxy Derivatives: A Theoretical-Experimental Study." Chemistry - A European Journal 19, no. 21 (April 16, 2013): 6598–612. http://dx.doi.org/10.1002/chem.201300662.

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27

Wille, Uta, and Christian Plath. "Transannular Cyclizations of Medium-Sized Cycloalkynes and Cycloalkynones Induced by Electro- and Photochemically Generated NO3 Radicals." Liebigs Annalen 1997, no. 1 (January 1997): 111–19. http://dx.doi.org/10.1002/jlac.199719970117.

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28

Ponomarenko, Maxim V., Yurii A. Serguchev, Bogdan V. Ponomarenko, Gerd-Volker Röschenthaler, and Andrey A. Fokin. "Experimental and theoretical studies on the transannular cyclizations of 3,7-dimethylenebicyclo[3.3.1]nonane with polyfluoroalkyl radicals." Journal of Fluorine Chemistry 127, no. 7 (July 2006): 842–49. http://dx.doi.org/10.1016/j.jfluchem.2006.03.006.

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29

Arencibia, Teresa, Thierry Prangé, JoséA Salazar, and Ernesto Suárez. "Alkoxy radical-induced transannular cyclizations of a substituted (E)-5-cyclodecenone derivative: Synthesis of bicyclo[5.3.0]decanes." Tetrahedron Letters 36, no. 35 (August 1995): 6337–40. http://dx.doi.org/10.1016/0040-4039(95)01225-7.

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30

Azarken, Redouan, Francisco M. Guerra, F. Javier Moreno-Dorado, Zacarías D. Jorge, and Guillermo M. Massanet. "Substituent effects in the transannular cyclizations of germacranes. Synthesis of 6-epi-costunolide and five natural steiractinolides." Tetrahedron 64, no. 48 (November 2008): 10896–905. http://dx.doi.org/10.1016/j.tet.2008.09.017.

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31

COLCLOUGH, D., J. B. WHITE, W. B. SMITH, and Y. CHU. "ChemInform Abstract: Electrophilic and Radical Transannular Cyclizations of 5-Cyclodecenone to Give Either Hydronaphthalene or Hydroazulene Products." ChemInform 25, no. 10 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199410100.

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32

Wille, Uta. "Sulfate Radical Anions (SO4•-) as Donor of Atomic Oxygen in Anionic Transannular, Self-Terminating, Oxidative Radical Cyclizations." Organic Letters 2, no. 22 (November 2000): 3485–88. http://dx.doi.org/10.1021/ol006527y.

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33

DOI, T., and T. TAKAHASHI. "ChemInform Abstract: Macroring Contraction Methodology. Part 5. Syntheses and Transannular Cyclizations of Neocarzinostatin-Chromophore and Esperamicin- Calichemicin Analogues." ChemInform 22, no. 42 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199142304.

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34

Biji, Mohanan, Kokkuvayil Vasu Radhakrishnan, and Ravi S. Lankalapalli. "Tandem Photoisomerization and Transannular Cyclizations of Zerumbone Epoxide: A Model for Diversity-Oriented Synthesis Using Abundant Natural Products." Organic Letters 23, no. 15 (July 13, 2021): 5871–75. http://dx.doi.org/10.1021/acs.orglett.1c01997.

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35

ARENCIBIA, T., T. PRANGE, J. SALAZAR, and E. SUAREZ. "ChemInform Abstract: Alkoxy Radical Induced Transannular Cyclizations of a Substituted (E)- 5-Cyclodecenone Derivative: Synthesis of Bicyclo(5.3.0)decanes." ChemInform 26, no. 51 (August 16, 2010): no. http://dx.doi.org/10.1002/chin.199551236.

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36

TOCHTERMANN, W., T. HABECK, C. WOLFF, E. M. PETERS, K. PETERS, and H. G. VON SCHNERING. "ChemInform Abstract: Synthesis of Medium and Large Rings. Part 35. Functionalized Hydroazulenones by Transannular Cyclizations of Dimethyl 10-Oxo-3,6- hexanooxepine-4,5-dicarboxylate." ChemInform 25, no. 24 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199424191.

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37

Samame, Renzo A., Christina M. Owens, and Scott D. Rychnovsky. "Concise synthesis of (+)-fastigiatine." Chemical Science 7, no. 1 (2016): 188–90. http://dx.doi.org/10.1039/c5sc03262h.

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38

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 (June 1, 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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39

Leitner, Christian, and Tanja Gaich. "Total synthesis of (±)-20S-hydroxy-1,2-dehydro-pseudoaspidospermidine via a C–H activation/transannular cyclization strategy." Chemical Communications 53, no. 54 (2017): 7451–53. http://dx.doi.org/10.1039/c7cc02699d.

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40

de Pascual Teresa, J., M. S. González, M. C. Caballero, T. Parra, and I. S. Bellido. "Transannular cyclization of heliangolides." Tetrahedron Letters 28, no. 7 (January 1987): 821–24. http://dx.doi.org/10.1016/s0040-4039(01)80999-0.

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41

Tang, Hao-Yu, Jin-Ming Gao, and Qiang Zhang. "Endophyte inspired chemical diversity from beta-caryophyllene." RSC Advances 5, no. 88 (2015): 72433–36. http://dx.doi.org/10.1039/c5ra14243a.

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The natural product (−)-β-caryophyllene is considered as an ideal initiator to generate diverse scaffolds by transannular cyclization due to its macrocyclic structure and abundant availability in nature.

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42

Porter, Ned A., Vincent H. T. Chang, David R. Magnin, and Bruce T. Wright. "Free-radical macrocyclization-transannular cyclization." Journal of the American Chemical Society 110, no. 11 (May 1988): 3554–60. http://dx.doi.org/10.1021/ja00219a034.

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43

Rodriguez-Hahn, Lydia, Jorge Cardenas, Emma Maldonado, Alfredo Ortega, Mariano Martinez, Manuel Soriano Garcia, and Alfredo Toscano. "Transannular cyclization of glaucolide A." Journal of Organic Chemistry 53, no. 13 (June 1988): 2965–68. http://dx.doi.org/10.1021/jo00248a012.

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44

Langlois, Pascal, Pierre Soucy, Yves L. Dory, and Pierre Deslongchamps. "Transannular Diels–Alder cyclization of substituted 13-membered trienes. An approach to the B.C.D.[6.6.5] rings of the 14β-hydroxysteroids." Canadian Journal of Chemistry 74, no. 2 (February 1, 1996): 129–43. http://dx.doi.org/10.1139/v96-017.

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The transannular Diels–Alder strategy has been applied to three 13-membered macrocyclic trienes whose characteristics are: a cis-trans diene and a cis methoxymethyl enol ether as the diénophile. The successful trials led to three 6.6.5 tricyles having a trans-syn-cis geometry exactly as in the B.C.D. rings of the 14β-hydroxysteroids. Key words: transannular, Diels–Alder, 14β-hydroxysteroids, 13-membered rings.

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45

Basak, Amit, Sandip Kumar Roy, and Subrata Mandal. "Activation of Macrocyclic Enediynes by Transannular Cyclization." Angewandte Chemie International Edition 44, no. 1 (January 2005): 132–35. http://dx.doi.org/10.1002/anie.200460831.

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46

Basak, Amit, Sandip Kumar Roy, and Subrata Mandal. "Activation of Macrocyclic Enediynes by Transannular Cyclization." Angewandte Chemie 117, no. 1 (January 2005): 134–37. http://dx.doi.org/10.1002/ange.200460831.

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47

Ader, Tammy A., Christine A. Champey, Larissa V. Kuznetsova, Tindy Li, Yeon-Hee Lim, David Rucando, and Scott McN Sieburth. "Polyquinanes by [4 + 4] Cycloaddition−Transannular Cyclization." Organic Letters 3, no. 14 (July 2001): 2165–67. http://dx.doi.org/10.1021/ol016076x.

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48

Krstic, Natalija, Mira Bjelakovic, Ljubinka Lorenc, and Vladimir Pavlovic. "Oxidative fragmentation of 5-hydroxy-1-oxo-5α-cholestan-3β-yl acetate." Journal of the Serbian Chemical Society 68, no. 11 (2003): 785–94. http://dx.doi.org/10.2298/jsc0311785k.

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5-hydroxy-1-oxo-5?-cholestan-3?-yl acetate (11) was prepared in 5 steps starting from (E)-3?-acetoxy-5,10-seco-1(10)-cholesten-5-one (6). Treatment of the 1-oxo-5-hydroxy derivative 11 with lead tetraacetate (LTA) (under thermal or hypoiodite conditions) or with mercuric oxide/iodine (HgO/I2) reagent resulted in the oxidative ?-fragmentation of the C(5)?C(10) bond affording 1,5-dioxo-5,10-secocholest-10(19)-en-3?-yl acetate (12), in different yields, depending on the reagent. Also the stereochemistry of the 1?,6?-cyclization product 13, formed by transannular cyclization of the 1,5-diketone 12 on silica gel, is discussed in this work.

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49

Harding, Charles E., and G. Richard Stanford. "Mechanism of the transannular cyclization of 5-cyclodecynone." Journal of Organic Chemistry 54, no. 13 (June 1989): 3054–56. http://dx.doi.org/10.1021/jo00274a018.

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50

Adekenov, S. M., N. M. Gafurov, K. M. Turdybekov, S. V. Lindeman, and Yu T. Struchkov. "Transannular cyclization of the E,E-germacradienolide hanphyllin." Chemistry of Natural Compounds 28, no. 5 (September 1992): 444–51. http://dx.doi.org/10.1007/bf00630647.

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