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Journal articles on the topic 'Carbocycle'

Author: Grafiati

Published: 4 June 2021

Last updated: 3 February 2022

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1

Xie, Xiu-Ying, Wei-Tao Jiang, and Bin Xiao. "Alkyl Carbagermatrane Enabled Synthesis of Seven-Membered Carbocycle-Fused Aromatics through Catellani Strategy." Synthesis 53, no. 16 (May 18, 2021): 2819–27. http://dx.doi.org/10.1055/s-0040-1720693.

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Synthesis of seven-membered carbocycle-fused aromatics was realized by Catellani reaction using terminally brominated alkyl carbagermatranes through intermolecular cyclization manner. Various functional groups were well tolerated, and this transformation was also expanded to the synthesis of carbocycles of other size. The utility of this method was demonstrated by modification of natural product derivatives and synthesis of bioactive molecules.

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2

Aimon, Anthony, Louis J. Farrugia, and J. Stephen Clark. "Synthesis of the Core Framework of the Cornexistins by Intramolecular Nozaki-Hiyama-Kishi Coupling." Molecules 24, no. 14 (July 22, 2019): 2654. http://dx.doi.org/10.3390/molecules24142654.

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A new and direct approach to the construction of the core framework of the herbicidal natural products cornexistin and hydroxycornexistin has been developed. Formation of the nine-membered carbocycle found in the natural products has been accomplished by an intramolecular Nozaki-Hiyama-Kishi reaction between a vinylic iodide and an aldehyde. Good yields of carbocyclic products were obtained from the reaction, but diastereomeric mixtures of allylic alcohols were produced. The cyclisation reaction was successful irrespective of the relative configuration of the stereogenic centres in the cyclisation precursor.

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3

Wang, Zhuo, and Junyang Liu. "All-carbon [3 + 2] cycloaddition in natural product synthesis." Beilstein Journal of Organic Chemistry 16 (December 9, 2020): 3015–31. http://dx.doi.org/10.3762/bjoc.16.251.

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Many natural products possess interesting medicinal properties that arise from their intriguing chemical structures. The highly-substituted carbocycle is one of the most common structural features in many structurally complicated natural products. However, the construction of highly-substituted, stereo-congested, five-membered carbocycles containing all-carbon quaternary center(s) is, at present, a distinct challenge in modern synthetic chemistry, which can be accessed through the all-carbon [3 + 2] cycloaddition. More importantly, the all-carbon [3 + 2] cycloaddition can forge vicinal all-carbon quaternary centers in a single step and has been demonstrated in the synthesis of complex natural products. In this review, we present the development of all-carbon [3 + 2] cycloadditions and illustrate their application in natural product synthesis reported in the last decade covering 2011–2020 (inclusive).

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4

Navaratne, Primali V., and Alexander J. Grenning. "Deconjugative alkylation/Heck reaction as a simple platform for dihydronaphthalene synthesis." Organic & Biomolecular Chemistry 15, no. 1 (2017): 69–75. http://dx.doi.org/10.1039/c6ob02250b.

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5

Han, Lingli, and Tao Liu. "A theoretical study on the palladium-catalyzed oxidative carbocyclization–alkoxycarbonylation of bisallenes to construct seven-membered carbocycles assisted by olefins." Organic & Biomolecular Chemistry 15, no. 23 (2017): 5055–61. http://dx.doi.org/10.1039/c7ob01161j.

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6

Tsukamoto, Hirokazu, Ayumu Kawase, and Takayuki Doi. "Asymmetric palladium-catalyzed umpolung cyclization of allylic acetate-aldehyde using formate as a reductant." Chemical Communications 51, no. 38 (2015): 8027–30. http://dx.doi.org/10.1039/c5cc02176f.

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Asymmetic palladium/chiral diphosphine-catalyzed umpolung cyclization of allylic acetate-aldehyde using formate as a reductant affordscis-disubstituted pyrrolidine, tetrahydrofuran, and spiro carbocycle.

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7

Abboud, K. A., E. J. Enholm, and A. Trivellas. "Structure of a densely oxygenated carbocycle." Acta Crystallographica Section C Crystal Structure Communications 48, no. 2 (February 15, 1992): 370–72. http://dx.doi.org/10.1107/s0108270191008879.

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8

Abboud, K. A., E. J. Enholm, and A. Trivellas. "Structure of a densely oxygenated carbocycle." Acta Crystallographica Section C Crystal Structure Communications 48, no. 9 (September 15, 1992): 1695–98. http://dx.doi.org/10.1107/s0108270192001033.

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9

Larock, Richard C., Qingping Tian, and Alexandre A. Pletnev. "Carbocycle Synthesis via Carbopalladation of Nitriles." Journal of the American Chemical Society 121, no. 13 (April 1999): 3238–39. http://dx.doi.org/10.1021/ja984086w.

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10

Desenko, S. M., K. �strada, V. D. Orlov, and O. A. Ponomarev. "Carbocycle annelated 1,2,4-triazolo[1,5-?]pyrimidines." Chemistry of Heterocyclic Compounds 27, no. 1 (January 1991): 88–91. http://dx.doi.org/10.1007/bf00633226.

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11

Sun, Zhaocui, Nailiang Zhu, Man Zhou, Xiaowei Huo, Haifeng Wu, Yu Tian, Junshan Yang, Guoxu Ma, Yan-Long Yang, and Xudong Xu. "Clavipines A–C, antiproliferative meroterpenoids with a fused azepine skeleton from the basidiomycete Clitocybe clavipes." Organic Chemistry Frontiers 6, no. 22 (2019): 3759–65. http://dx.doi.org/10.1039/c9qo01005j.

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Three novel meroterpenoids, clavipines A–C (1–3), possessing a benzoquinone fused to an azepine ring and a ten-membered carbocycle with α,β-epoxy/unsaturated-γ-lactone, were isolated from the basidiomycete Clitocybe clavipes.

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12

Howard, Siân T., and Ian A. Fallis. "A ‘triylide carbocycle’: cyclononane-1,4,7-triammonium triylide." Journal of the Chemical Society, Perkin Transactions 2, no. 11 (1998): 2335–36. http://dx.doi.org/10.1039/a805600e.

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13

Nakashima, Katsuyuki, Yuzuru Kondo, Kosei Yoshimasu, Masakazu Sono, and Motoo Tori. "Synthesis of Chiral Hexasubstituted Cyclohexanediol, a Key Intermediate for the Synthesis of Verticillol, from (+)-Dihydrocarvone; Attempted Cyclization to 12-Membered Carbocycle in Verticillol using RCM Reaction." Natural Product Communications 10, no. 4 (April 2015): 1934578X1501000. http://dx.doi.org/10.1177/1934578x1501000402.

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A cyclohexane derivative with three chiral centers, a key intermediate for the synthesis of a diterpene verticillol, was prepared starting from (+)-dihydrocarvone. A further challenge to cyclize to a 12-membered carbocycle was attempted, although the products were dimeric derivatives presumably due to an undesirable conformation of the substrate.

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14

Nakashima, Katsuyuki, Naoki Kikuchi, Tasuku Takehara, Takayuki Shiozawa, Shigeru Takaoka, and Motoo Tori. "Synthesis of a Key Intermediate, 10-Acetyl-7-(t-butyldiphenylsilyloxymethyl)-4-methylbicyclo[5.3.0]dec-4-en-1-ol, in the Synthesis of Pseudolaric Acid A." Natural Product Communications 8, no. 7 (July 2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800707.

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10-Acetyl-7-( t-butyldiphenylsilyloxymethyl)-4-methylbicyclo[5.3.0]dec-4-en-1-ol was synthesized by aldol cyclization to a five-membered ring, epoxidation, samarium diiodide-induced ring opening, and the RCM reaction to the seven-membered carbocycle. This method has succeeded in constructing the desired stereochemistry in the synthesis of pseudolaric acid A.

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15

Griffiths, Peter R., Don E. Pivonka, and Richard Vaughan Williams. "The Experimental Realization of a Neutral Homoaromatic Carbocycle." Chemistry - A European Journal 17, no. 33 (July 6, 2011): 9193–99. http://dx.doi.org/10.1002/chem.201100025.

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16

LI, C. J., D. L. CHEN, Y. Q. LU, J. X. HABERMAN, and J. T. MAGUE. "ChemInform Abstract: Novel Carbocycle Enlargement in Aqueous Medium." ChemInform 27, no. 34 (August 5, 2010): no. http://dx.doi.org/10.1002/chin.199634090.

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17

Larock, Richard C., Qingping Tian, and Alexandre A. Pletnev. "ChemInform Abstract: Carbocycle Synthesis via Carbopalladation of Nitriles." ChemInform 30, no. 29 (June 14, 2010): no. http://dx.doi.org/10.1002/chin.199929055.

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18

Palani, Namasivayam, Sengottuvelan Balasubramanian, and Tarur Dinesh. "Intramolecular Radical Cyclization of Vinyl, Aryl and Alkyl Halides Using Catalytic Amount of Bis-tri-n-butyltin Oxide/Sodium Borohydride: A Novel Entry to Functionalized Carbocycles." Synlett 26, no. 08 (March 17, 2015): 1055–58. http://dx.doi.org/10.1055/s-0034-1380325.

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We wish to report a facile method in which a catalytic amount of bis-tri-n-butyltinoxide (TBTO) in the presence of sodium borohydride efficiently brings about the intramolecular radical cyclization of a variety of vinyl, aryl and alkyl halides to their corresponding functionalized bicyclic and tricyclic carbocycle frameworks. The methodology obviates the need for stoichiometric amounts of tin reagent normally required for radical cyclization reactions.

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19

Yang, Eugene G., Karthik Sekar, and Martin J. Lear. "A macrolactonisation approach to the cembrane carbocycle of bielschowskysin." Tetrahedron Letters 54, no. 33 (August 2013): 4406–8. http://dx.doi.org/10.1016/j.tetlet.2013.06.012.

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20

Li, Chao-Jun, Dong-Li Chen, Yue-Qi Lu, John X. Haberman, and Joel T. Mague. "Metal-mediated two-atom carbocycle enlargement in aqueous medium." Tetrahedron 54, no. 11 (March 1998): 2347–64. http://dx.doi.org/10.1016/s0040-4020(98)00004-0.

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21

Nevalainen, Marta, and Ari M. P. Koskinen. "Synthesis of a 10-Membered Carbocycle By Olefin Metathesis." Angewandte Chemie International Edition 41, no. 1 (January 2, 2002): 16. http://dx.doi.org/10.1002/1521-3773(20020104)41:1<16::aid-anie16>3.0.co;2-b.

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22

Nevalainen, Marta, and Ari M. P. Koskinen. "Synthesis of a 10-Membered Carbocycle By Olefin Metathesis." Angewandte Chemie 113, no. 21 (November 5, 2001): 4184–86. http://dx.doi.org/10.1002/1521-3757(20011105)113:21<4184::aid-ange4184>3.0.co;2-r.

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23

Nevalainen, Marta, and Ari M. P. Koskinen. "Synthesis of a 10-Membered Carbocycle By Olefin Metathesis." Angewandte Chemie 114, no. 1 (January 4, 2002): 16. http://dx.doi.org/10.1002/1521-3757(20020104)114:1<16::aid-ange16>3.0.co;2-q.

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24

Aumüller, Ingo B., and Jari Yli-Kauhaluoma. "Computational methods for analysis of an unsaturated carbocycle: heptafulvene." Theoretical Chemistry Accounts 126, no. 1-2 (November 13, 2009): 55–73. http://dx.doi.org/10.1007/s00214-009-0675-0.

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25

Huber, Tatjana, Lara Weisheit, and Thomas Magauer. "Synthesis of Xenia diterpenoids and related metabolites isolated from marine organisms." Beilstein Journal of Organic Chemistry 11 (December 10, 2015): 2521–39. http://dx.doi.org/10.3762/bjoc.11.273.

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This review describes strategies for the chemical synthesis of xenicane diterpenoids and structurally related metabolites. Selected members from the four different subclasses of the Xenia diterpenoid family, the xenicins, xeniolides, xeniaphyllanes and xeniaethers, are presented. The synthetic strategies are discussed with an emphasis on the individual key reactions for the construction of the uncommon nine-membered carbocycle which is the characteristic structural feature of these natural products. Additionally, the putative biosynthetic pathway of xenicanes is illustrated.

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26

Jeon, Byung-sun, Mark W. Ruszczycky, William K. Russell, Geng-Min Lin, Namho Kim, Sei-hyun Choi, Shao-An Wang, et al. "Investigation of the mechanism of the SpnF-catalyzed [4+2]-cycloaddition reaction in the biosynthesis of spinosyn A." Proceedings of the National Academy of Sciences 114, no. 39 (September 5, 2017): 10408–13. http://dx.doi.org/10.1073/pnas.1710496114.

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The Diels–Alder reaction is one of the most common methods to chemically synthesize a six-membered carbocycle. While it has long been speculated that the cyclohexene moiety found in many secondary metabolites is also introduced via similar chemistry, the enzyme SpnF involved in the biosynthesis of the insecticide spinosyn A in Saccharopolyspora spinosa is the first enzyme for which catalysis of an intramolecular [4+2]-cycloaddition has been experimentally verified as its only known function. Since its discovery, a number of additional standalone [4+2]-cyclases have been reported as potential Diels–Alderases; however, whether their catalytic cycles involve a concerted or stepwise cyclization mechanism has not been addressed experimentally. Here, we report direct experimental interrogation of the reaction coordinate for the [4+2]-carbocyclase SpnF via the measurement of α-secondary deuterium kinetic isotope effects (KIEs) at all sites of sp2→sp3 rehybridization for both the nonenzymatic and enzyme-catalyzed cyclization of the SpnF substrate. The measured KIEs for the nonenzymatic reaction are consistent with previous computational results implicating an intermediary state between formation of the first and second carbon–carbon bonds. The KIEs measured for the enzymatic reaction suggest a similar mechanism of cyclization within the enzyme active site; however, there is evidence that conformational restriction of the substrate may play a role in catalysis.

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27

Chen, Xiaoyu, Andrew Thomas Holm, and Philip Wai Hong Chan. "Gold Catalysed 1,4-Enyne Acetate Strategy for the Synthesis of 1H-Indenes and Partially Hydrogenated Methanonaphtho[1,2-c]furan-1,3(4H)-diones." Australian Journal of Chemistry 73, no. 12 (2020): 1165. http://dx.doi.org/10.1071/ch20175.

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A synthetic method to prepare 1H-indenes and partially hydrogenated methanonaphtho[1,2-c]furan-1,3(4H)-diones from gold(i)-catalysed 1,4-enyne acetate cycloisomerisation and oxidation or Diels–Alder reaction with maleic anhydride is described. The proposed mechanism involves Rautenstrauch rearrangement of the 1,4-enyne motif to give an insitu formed 1,3-cyclopentadiene intermediate. This is followed by 6-endo-dig cyclisation of the cyclic adduct and oxidation to give the aromatic carbocycle or Diels–Alder reaction with maleic anhydride to afford the bridged furan product.

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28

Harrowven, David C., Timothy Woodcock, and Peter D. Howes. "A tandem Heck reaction leading to a 26-membered carbocycle." Tetrahedron Letters 43, no. 51 (December 2002): 9327–29. http://dx.doi.org/10.1016/s0040-4039(02)02343-2.

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29

Haberman, John X., and Chao-Jun Li. "Indium and zinc mediated one-atom carbocycle enlargement in water." Tetrahedron Letters 38, no. 27 (July 1997): 4735–36. http://dx.doi.org/10.1016/s0040-4039(97)01024-1.

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30

Peng, Bo, Xiujuan Feng, Xin Zhang, Sheng Zhang, and Ming Bao. "Propargylic and Allenic Carbocycle Synthesis through Palladium-Catalyzed Dearomatization Reaction." Journal of Organic Chemistry 75, no. 8 (April 16, 2010): 2619–27. http://dx.doi.org/10.1021/jo100211d.

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31

Swamy, Nalivela Kumara, Lakshmi Kumar Tatini, J. Moses Babu, Pazhanimuthu Annamalai, and Manojit Pal. "Pd-mediated synthesis of substituted benzenes fused with carbocycle/heterocycle." Chemical Communications, no. 10 (2007): 1035. http://dx.doi.org/10.1039/b612770c.

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32

Xie, Xin, Wei Huang, Cheng Peng, and Bo Han. "Organocatalytic Asymmetric Synthesis of Six-Membered Carbocycle-Based Spiro Compounds." Advanced Synthesis & Catalysis 360, no. 2 (November 16, 2017): 194–228. http://dx.doi.org/10.1002/adsc.201700927.

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33

Chen, Shi, Gang Shan, Pengju Nie, and Yu Rao. "3-Alkyloxycyclobutanones as Useful Synthons for Heterocycle and Carbocycle Synthesis." Asian Journal of Organic Chemistry 4, no. 1 (December 2, 2014): 16–26. http://dx.doi.org/10.1002/ajoc.201402200.

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34

ABBOUD, K. A., E. J. ENHOLM, and A. TRIVELLAS. "ChemInform Abstract: Structure of a Densely Oxygenated Carbocycle. Part 2." ChemInform 23, no. 51 (December 22, 1992): no. http://dx.doi.org/10.1002/chin.199251282.

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35

Hams, Arthur E., and John R. Stille. "Carbocycle formation via intramolecular insertion of alkynes into titanium-carbon bonds." Tetrahedron Letters 33, no. 44 (October 1992): 6565–68. http://dx.doi.org/10.1016/s0040-4039(00)60986-3.

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36

Fráter, Georg. "Book Review: Carbocycle Construction in Terpene Synthesis. By Tse-Lok Ho." Angewandte Chemie International Edition in English 28, no. 11 (November 1989): 1537. http://dx.doi.org/10.1002/anie.198915371.

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37

LI, C. J., D. L. CHEN, Y. Q. LU, J. X. HABERMAN, and J. T. MAGUE. "ChemInform Abstract: Metal-Mediated Two-Atom Carbocycle Enlargement in Aqueous Medium." ChemInform 29, no. 25 (June 22, 2010): no. http://dx.doi.org/10.1002/chin.199825096.

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38

Yamazaki, Shoko. "ChemInform Abstract: Development of Novel Carbocycle Forming Reactions Using Vinyl Selenides." ChemInform 31, no. 32 (June 3, 2010): no. http://dx.doi.org/10.1002/chin.200032241.

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39

Nevalainen, Marta, and Ari M. P. Koskinen. "ChemInform Abstract: Synthesis of a 10-Membered Carbocycle by Olefin Metathesis." ChemInform 33, no. 9 (May 22, 2010): no. http://dx.doi.org/10.1002/chin.200209172.

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40

Schuster, Christopher H., John R. Coombs, Zachary A. Kasun, and James P. Morken. "Enantioselective Carbocycle Formation through Intramolecular Pd-Catalyzed Allyl–Aryl Cross-Coupling." Organic Letters 16, no. 17 (August 8, 2014): 4420–23. http://dx.doi.org/10.1021/ol5019163.

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41

Aurrecoechea, José M., Mónica Arrate, Jesús H. Gil, and Beatriz López. "Direct carbohydrate to carbocycle conversions via intramolecular allylation with Et2Zn/Pd(0)." Tetrahedron 59, no. 29 (July 2003): 5515–22. http://dx.doi.org/10.1016/s0040-4020(03)00825-1.

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42

Urabe, Hirokazu, Miho Narita, and Fumie Sato. "A Titanacycle-to-Carbocycle Relay Leading to an Expedient Synthesis of Cyclopentadienols." Angewandte Chemie International Edition 38, no. 23 (November 30, 1999): 3516–18. http://dx.doi.org/10.1002/(sici)1521-3773(19991203)38:23<3516::aid-anie3516>3.0.co;2-0.

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43

Chen, Shi, Gang Shan, Pengju Nie, and Yu Rao. "ChemInform Abstract: 3-Alkyloxycyclobutanones as Useful Synthons for Heterocycle and Carbocycle Synthesis." ChemInform 46, no. 14 (March 19, 2015): no. http://dx.doi.org/10.1002/chin.201514323.

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44

HABERMAN, J. X., and C. J. LI. "ChemInform Abstract: Indium and Zinc Mediated One-Atom Carbocycle Enlargement in Water." ChemInform 28, no. 40 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199740059.

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45

Peng, Bo, Xiujuan Feng, Xin Zhang, Sheng Zhang, and Ming Bao. "ChemInform Abstract: Propargylic and Allenic Carbocycle Synthesis Through Palladium-Catalyzed Dearomatization Reaction." ChemInform 41, no. 36 (August 12, 2010): no. http://dx.doi.org/10.1002/chin.201036054.

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46

Na, Hai-Sub, Yasuhiro Morisaki, Yasuhiro Aiki, and Yoshiki Chujo. "Synthesis of Conjugated Polymers Containing Phosphole with the 5-Member Fused Carbocycle." Polymer Bulletin 58, no. 4 (November 14, 2006): 645–52. http://dx.doi.org/10.1007/s00289-006-0702-4.

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47

Kamernitskii, Alexey V., V. N. Ignatov, and Inna S. Levina. "Photochemical Methods for the Construction of an Additional Four-membered Carbocycle in Steroids." Russian Chemical Reviews 57, no. 3 (March 31, 1988): 270–82. http://dx.doi.org/10.1070/rc1988v057n03abeh003349.

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48

Wang, Zhao, Yuhui Huang, Jia Guo, Zhenhua Li, Jiangtao Xu, Jennifer Q. Lu, and Changchun Wang. "Design and Synthesis of Thermal Contracting Polymer with Unique Eight-Membered Carbocycle Unit." Macromolecules 51, no. 4 (February 9, 2018): 1377–85. http://dx.doi.org/10.1021/acs.macromol.7b02705.

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49

Schuster, Christopher H., John R. Coombs, Zachary A. Kasun, and James P. Morken. "ChemInform Abstract: Enantioselective Carbocycle Formation Through Intramolecular Pd-Catalyzed Allyl-Aryl Cross-Coupling." ChemInform 46, no. 10 (February 19, 2015): no. http://dx.doi.org/10.1002/chin.201510034.

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50

Shundrin, Leonid A., Irina G. Irtegova, Nadezhda V. Vasilieva, Pavel A. Avrorov, Natalia Yu Selikhova, Arkady G. Makarov, Alexander Yu Makarov, Yuri G. Slizhov, and Andrey V. Zibarev. "Electrochemical properties and radical anions of carbocycle-fluorinated quinoxalines and their substituted derivatives." Journal of Physical Organic Chemistry 30, no. 8 (November 29, 2016): e3667. http://dx.doi.org/10.1002/poc.3667.

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