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Journal articles on the topic 'Spirocycle'

Author: Grafiati

Published: 4 June 2021

Last updated: 13 February 2022

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1

Wollenweber, Markus, Reinhart Keese, and Helen Stoeckli-Evans. "Synthesis of Spirocyclic Aminosilanes with Electron Withdrawing Substituents at Nitrogen." Zeitschrift für Naturforschung B 53, no. 2 (February 1, 1998): 145–48. http://dx.doi.org/10.1515/znb-1998-0202.

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Abstract The first synthesis of spirocyclic tetrasulfonamidosilanes is described. According to the X-Ray structure analysis of the most stable tetratosylamidosilane obtained the Silicon is bonded to four Nitrogen atoms in a spirocycle and surrounded by four Oxygen atoms which are located above the planes of the SiN4 tetrahedron.

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2

Charlton, M. Anne, and James R. Green. "Formation of quaternary centres via iron allyl cations. Rapid entry into spirocyclic ring systems." Canadian Journal of Chemistry 75, no. 7 (July 1, 1997): 965–74. http://dx.doi.org/10.1139/v97-116.

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Ester-substituted allyltetracarbonyliron cations react with cycloalkylidene-type silyl enol ethers, silyl ketene acetals, and β-keto-esters to give 1,6-dicarbonyl compounds containing a newly formed quaternary centre. Selected condensation products are converted by enolate chemistry into spirocyclic [4.4], [4.5], and [4.6] systems. Acyloin and other reductive cyclization reactions are employed to convert the condensation products into spirocyclic [4.5], [5.5], and [5.6] systems. Keywords: allyliron complexes, umpolung synthesis, 1,6-dicarbonyls, spirocycle synthesis.

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3

Ji, Yanling, Xianghong He, Cheng Peng, and Wei Huang. "Recent advances in the synthesis of C2-spiropseudoindoxyls." Organic & Biomolecular Chemistry 17, no. 11 (2019): 2850–64. http://dx.doi.org/10.1039/c8ob03122c.

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4

Klika Škopić, Mateja, Suzanne Willems, Bernd Wagner, Justin Schieven, Norbert Krause, and Andreas Brunschweiger. "Exploration of a Au(i)-mediated three-component reaction for the synthesis of DNA-tagged highly substituted spiroheterocycles." Org. Biomol. Chem. 15, no. 40 (2017): 8648–54. http://dx.doi.org/10.1039/c7ob02347b.

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5

Xue, Bingxiang, Shikuan Su, Yongmei Cui, Youwen Fei, Xueshun Jia, Jian Li, and Jianhui Fang. "Phosphine-mediated sequential annulations of allenyl ketone and isocyanide: a bicyclization strategy to access a furan-fused eight-membered ring and a spirocycle." Chemical Communications 55, no. 81 (2019): 12180–83. http://dx.doi.org/10.1039/c9cc06267j.

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6

Huang, Ji-Rong, Liu Qin, Yu-Qin Zhu, Qiang Song, and Lin Dong. "Multi-site cyclization via initial C–H activation using a rhodium(iii) catalyst: rapid assembly of frameworks containing indoles and indolines." Chemical Communications 51, no. 14 (2015): 2844–47. http://dx.doi.org/10.1039/c4cc07125e.

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Tandem multi-site cyclization triggered by Rh(iii)-catalyzed C–H activation has been achieved for highly efficient synthesis of spirocycle indolin-3-one (C2-cyclization), benzo[a]carbazole (C3-cyclization) and an unusual indoxyl core (N1-cyclization).

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7

Farat, Oleg, Svetlana Varenichenko, Ekaterina Zaliznaya, and Victor Markov. "REARRANGEMENT OF SUBSTITUTED 1,3-BENZOXAZINES INTO XANTHENE-TYPE COMPOUNDS." Ukrainian Chemistry Journal 86, no. 2 (February 5, 2020): 111–22. http://dx.doi.org/10.33609/0041-6045.86.2.2020.111-122.

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The rearrangement patterns of new 1,3-benzoxazines derivatives obtained by condensation of substituted salicylamides with cyclic ketones under the influence of Vilsmeier-Haack reagent has been studied. The influence of angel strain in a 4-membered spirocycle prevents the rearrangement of spiro [1,3-benzoxazine-2,1'-cyclobutan]-4(3H)-one under the action of a formylating agent. 1,3-Benzoxazines derivatives with ring sizes from 5- to 8-membered under the action of a formylating agent have formed formylxanthene derivative. Their formation reaction rate depends on the presence of electronegativity substituents at positions C-6 and C-8 of the aromatic cycle, as well as in the spiroring. In this work, we presented an effective method for the synthesis of formyl derivatives of xanthenes based on readily available salicylamide. It was found that (spiro[1,3-benzoxazine-2,1'-cyclobutan]-4(3H)-one) does not rearrange even under prolonged heating due to the spirocycle strain. The presence of bromine or iodine atoms at positions C-6 and C-8 of the aromatic cycle of 1,3-benzoxazines makes the reaction more difficult, which requires more harsh synthesis conditions.

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8

Jiang, Chongguo, Sijia Chen, Jianxian Gong, and Zhen Yang. "Synthetic Study Toward the 4,5-Spirocycle Skeleton of Phainanoids." Acta Chimica Sinica 78, no. 9 (2020): 928. http://dx.doi.org/10.6023/a20060198.

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9

Bassindale, Martin J., Peter Hamley, Andreas Leitner, and Joseph P. A. Harrity. "Spirocycle assembly through selective tandem ring closing metathesis reactions." Tetrahedron Letters 40, no. 16 (April 1999): 3247–50. http://dx.doi.org/10.1016/s0040-4039(99)00375-5.

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10

Tkachuk, Anna V., Sergey V. Kurbatov, Pavel G. Morozov, and Gennadiy S. Borodkin. "The first dipolar spirocycle based on 10-(benzylamino)colchicine." Chemistry of Heterocyclic Compounds 51, no. 10 (October 2015): 948–50. http://dx.doi.org/10.1007/s10593-015-1803-5.

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11

Lv, Ningning, Yue Liu, Chunhua Xiong, Zhanxiang Liu, and Yuhong Zhang. "Cobalt-Catalyzed Oxidant-Free Spirocycle Synthesis by Liberation of Hydrogen." Organic Letters 19, no. 17 (August 21, 2017): 4640–43. http://dx.doi.org/10.1021/acs.orglett.7b02266.

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12

Kimura, Makoto, Shin-ichiro Inoue, Kou Shimada, Shizuo Tokito, Koji Noda, Yasunori Taga, and Yasuhiko Sawaki. "Spirocycle-Incorporated Triphenylamine Derivatives as an Advanced Organic Electroluminescent Material." Chemistry Letters 29, no. 2 (February 2000): 192–93. http://dx.doi.org/10.1246/cl.2000.192.

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13

Fraley, Amy E., Kersti Caddell Haatveit, Ying Ye, Samantha P. Kelly, Sean A. Newmister, Fengan Yu, Robert M. Williams, Janet L. Smith, K. N. Houk, and David H. Sherman. "Molecular Basis for Spirocycle Formation in the Paraherquamide Biosynthetic Pathway." Journal of the American Chemical Society 142, no. 5 (January 6, 2020): 2244–52. http://dx.doi.org/10.1021/jacs.9b09070.

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14

Bassindale, Martin J., Peter Hamley, Andreas Leitner, and Joseph P. A. Harrity. "ChemInform Abstract: Spirocycle Assembly Through Selective Tandem Ring Closing Metathesis Reactions." ChemInform 30, no. 27 (June 14, 2010): no. http://dx.doi.org/10.1002/chin.199927053.

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15

Li, Fang, and Steven L. Castle. "Synthesis of the Acutumine Spirocycle via a Radical−Polar Crossover Reaction." Organic Letters 9, no. 20 (September 2007): 4033–36. http://dx.doi.org/10.1021/ol701757f.

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16

Fominova, Kateryna, Taras Diachuk, Dmitry Granat, Taras Savchuk, Vladyslav Vilchynskyi, Oleksiy Svitlychnyi, Vladyslav Meliantsev, et al. "Oxa-spirocycles: synthesis, properties and applications." Chemical Science 12, no. 34 (2021): 11294–305. http://dx.doi.org/10.1039/d1sc03615g.

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17

Buckland, SJ, B. Halton, and PJ Stang. "Studies in the Cycloproparene Series: The Behavior of Alkylidenecycloproparenes Towards Nucleophiles and Oxidizing Agents." Australian Journal of Chemistry 41, no. 6 (1988): 845. http://dx.doi.org/10.1071/ch9880845.

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The alkylidenecycloproparene (1) reacts with potassium t- butoxide to give the ring-expanded heptafulvene (3). Epoxidation of (1) provides the hydroxy ketone (5) probably via the spiro epoxide (4) but carbene additions fail to give spirocycle (7). Photooxygenation of (1a,b) gives products (5),(12)-(14) and (16) which are explicable in terms of initial formation of dioxetan (10); products (13) and (14) result from 1H-cyclopropa[b] naphthalenone (11). By comparison (1c) provides phenanthraquinone acetal (17) in low yield. With osmium tetroxide and sodium periodate , (1a) gives benzophenone (12a) in competition with hydroxy ketone (5a) and 2,2-diphenylcyclobutanaphthalenone (20). The modes of formation of the various products are discussed.

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18

Klapötke, Thomas M., Sham Kumar Vasisht, and Peter Mayer. "Spirocycle (SitBu3)6Si9Cl2: The First of Its Kind among Group 14 Elements." European Journal of Inorganic Chemistry 2010, no. 21 (June 23, 2010): 3256–60. http://dx.doi.org/10.1002/ejic.201000498.

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19

Kimura, Makoto, Shin-ichiro Inoue, Kou Shimada, Shizuo Tokito, Koji Noda, Yasunori Taga, and Yasuhiko Sawaki. "ChemInform Abstract: Spirocycle-Incorporated Triphenylamine Derivatives as an Advanced Organic Electroluminescent Material." ChemInform 31, no. 23 (June 8, 2010): no. http://dx.doi.org/10.1002/chin.200023104.

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20

RAUBOLD, T., S. FREITAG, R. HERBST-IRMER, and H. W. ROESKY. "ChemInform Abstract: Synthesis and Crystal Structure of the Spirocycle ((iPr)2P(S)NSiMe3) 2SnCl2." ChemInform 24, no. 29 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199329220.

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21

Ray, Peter C., Margaret Huggett, Penelope A. Turner, Malcolm Taylor, Laura A. T. Cleghorn, Julie Early, Anuradha Kumar, et al. "Spirocycle MmpL3 Inhibitors with Improved hERG and Cytotoxicity Profiles as Inhibitors of Mycobacterium tuberculosis Growth." ACS Omega 6, no. 3 (January 13, 2021): 2284–311. http://dx.doi.org/10.1021/acsomega.0c05589.

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22

Xie, Jiaxin, Jianchun Wang, and Guangbin Dong. "Synthetic Study of Phainanoids. Highly Diastereoselective Construction of the 4,5-Spirocycle via Palladium-Catalyzed Intramolecular Alkenylation." Organic Letters 19, no. 11 (May 19, 2017): 3017–20. http://dx.doi.org/10.1021/acs.orglett.7b01303.

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23

Yang, Zheng, Likai Hao, Bing Yin, Mengyao She, Martin Obst, Andreas Kappler, and Jianli Li. "Six-Membered Spirocycle Triggered Probe for Visualizing Hg2+ in Living Cells and Bacteria–EPS–Mineral Aggregates." Organic Letters 15, no. 17 (August 12, 2013): 4334–37. http://dx.doi.org/10.1021/ol401795m.

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24

Best, Quinn A., Narsimha Sattenapally, Daniel J. Dyer, Colleen N. Scott, and Matthew E. McCarroll. "pH-Dependent Si-Fluorescein Hypochlorous Acid Fluorescent Probe: Spirocycle Ring-Opening and Excess Hypochlorous Acid-Induced Chlorination." Journal of the American Chemical Society 135, no. 36 (August 27, 2013): 13365–70. http://dx.doi.org/10.1021/ja401426s.

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25

Cacho, Ralph A., Yit-Heng Chooi, Hui Zhou, and Yi Tang. "Complexity Generation in Fungal Polyketide Biosynthesis: A Spirocycle-Forming P450 in the Concise Pathway to the Antifungal Drug Griseofulvin." ACS Chemical Biology 8, no. 10 (September 9, 2013): 2322–30. http://dx.doi.org/10.1021/cb400541z.

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26

Seto, Shigeki, Kazuhiko Yumoto, Kyoko Okada, Yoshikazu Asahina, Aya Iwane, Maki Iwago, Reiko Terasawa, Kevin R. Shreder, Koji Murakami, and Yasushi Kohno. "Quinolone derivatives containing strained spirocycle as orally active glycogen synthase kinase 3β (GSK-3β) inhibitors for type 2 diabetics." Bioorganic & Medicinal Chemistry 20, no. 3 (February 2012): 1188–200. http://dx.doi.org/10.1016/j.bmc.2011.12.046.

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27

Stokes, Francesca A., Lars Kloo, Philip J. Harford, Andrew J. Peel, Robert J. Less, Andrew E. H. Wheatley, and Dominic S. Wright. "Towards the Synthesis of Guanidinate- and Amidinate-Bridged Dimers of Mn and Ni." Australian Journal of Chemistry 67, no. 7 (2014): 1081. http://dx.doi.org/10.1071/ch14271.

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Reactions of Cp2M (Cp = cyclopentadienyl, M = Mn, Ni) with lithium amidinates and guanidinates are reported. The highly oxophilic nature of Mn leads to the isolation of the interstitial oxide Mn4O(MeN···CH···NMe)6 (4) in preference to the intended paddle-wheel homodimer Mn2(MeN···CH···NMe)4 when employing the sterically uncongested amidinate [MeN···CH···NMe]– ligand. In contrast, an analogous reaction using Cp2Ni yielded Ni2(MeN···CH···NMe)4 (5). The use of monoprotic guanidinate ligands also gave contrasting results for Mn and Ni. In the first case, the highly unusual spirocycle Mn{μ-NC(NMe2)2}4Li2·3THF (6) was produced in low yield. For M = Ni, use of the [hpp]– (1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidinate) ligand gives results comparable with the synthesis of 5, with Ni2(hpp)4 (7) isolated. In contrast to recent data obtained using Cp2Cr, the guanidinate ligands do not sequester coformed CpLi. Density functional theory analysis corroborates the view that the intermetal distance in each of the reported dinickel paddle-wheel complexes (2.4846(8) and 2.3753(5) Å in 5 and 7 respectively) is defined by the geometric parameters of the bidentate ligands and that intermetal bonding is not present.

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28

Böck, Barbara, Heinrich Nöth, and Ulrich Wietelmann. "Reactions of Amino-imino-boranes with Transition Metal Halides and Substituted Transition Metal Halides." Zeitschrift für Naturforschung B 56, no. 7 (July 1, 2001): 659–70. http://dx.doi.org/10.1515/znb-2001-0714.

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The aminoiminoborane tmp-B=NCMe3 (1) adds to TiBr4 or ZrCl4 in a 1:1 ratio while PdCl2 adds 1 in a 1:2 ratio. In these new compounds the NBN unit is almost linear and the configuration corresponds to an allene. On the other hand 1 and Ti(OR)4 compounds and Ti(NMe2)4 give N metallated diaminoboranes tmp-B(X)-NCMe3EX3 (X = OR, NMe2). Mixed compounds Ti(OR)3-nXn lead to diaminoboranes with BOR groups while the TiCl bond inserts into the B = N bond of 1 to produce tmp-BNMe2-NCMe3TiCl3. Hydrolysis of this compound leads to a spirocyclic dititanoxane with a short linear Ti-O-Ti bond and pentacoordinated Ti centers carrying two Cl atoms each. Spirocycles with a BN2E (E = Ti, Nb, Ta, Pd) unit are formed when 1 is allowed to react with TiCl4, NbCl5, TaCl5 and PdCl2. The palladium compound 16 is dimeric, and dimerization occurs via Pd-Cl bridges. The aminoiminoborane tmp-B=NC6H3-2,6-iPr2 reacts with the titanium compounds in the same manner as 1, however without formation of spirocycles.

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29

Gopalakrishnan, Janarthanan, Babu Varghese, Adinarayana Doddi, and M. N. Sudheendra Rao. "A new synthetic route to cyclophosphadithiatriazenes: synthesis and X-ray structural characterization of the first spirocycle containing thiadiazaphosphetidine and phosphadithiatriazene heterocycles." Applied Organometallic Chemistry 20, no. 12 (2006): 880–85. http://dx.doi.org/10.1002/aoc.1148.

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30

Kemmitt, T., and NB Milestone. "The Ring Size Influence on 29Si N.M.R. Chemical Shifts of Some Spirocyclic Tetra- and Penta-coordinate Diolato Silicates." Australian Journal of Chemistry 48, no. 1 (1995): 93. http://dx.doi.org/10.1071/ch9950093.

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A series of tetracoordinate spirocyclic silicates has been prepared from the reaction of a range of diols with tetraethoxysilane, Si ( OEt )4. The silicates can be converted into anionic pentacoordinate silicates by reaction with KOBut/18-crown-6 in toluene. Alternatively, the pentacoordinate spirocycles can be prepared directly without prior preparation of a tetracoordinate spiro silicate. 29Si n.m.r. studies have demonstrated that the chemical shifts are sensitive to both coordination number and ring size. Ring contributions to the 29Si chemical shifts are apparent for the five- membered ring spiro silicates, those for the pentcoordinate species being less than those for the tetracoordinate species. Acyclic and six- membered ring spiro silicates are virtually indistinguishable by 29Si n.m.r. spectroscopy, which demonstrates that no ring contribution to the chemical shift is apparent for this ring size.

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31

Majumdar, Anupam, Chang Su Lim, Hwan Myung Kim, and Kumaresh Ghosh. "New Six-Membered pH-Insensitive Rhodamine Spirocycle in Selective Sensing of Cu2+through C–C Bond Cleavage and Its Application in Cell Imaging." ACS Omega 2, no. 11 (November 20, 2017): 8167–76. http://dx.doi.org/10.1021/acsomega.7b01324.

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32

Fang, Min, Nathan D. Jones, Robert Lukowski, Jim Tjathas, Michael J. Ferguson, and Ronald G. Cavell. "A Bimetallic, Coordinated-Ketene Complex Formed from a Bimetallic Lithium–Carbon Spirocycle by Lithium-Mediated Insertion of CO into a Rhodium–Carbon Bond." Angewandte Chemie International Edition 45, no. 19 (May 5, 2006): 3097–101. http://dx.doi.org/10.1002/anie.200503814.

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33

Fang, Min, Nathan D. Jones, Robert Lukowski, Jim Tjathas, Michael J. Ferguson, and Ronald G. Cavell. "A Bimetallic, Coordinated-Ketene Complex Formed from a Bimetallic Lithium–Carbon Spirocycle by Lithium-Mediated Insertion of CO into a Rhodium–Carbon Bond." Angewandte Chemie 118, no. 19 (May 5, 2006): 3169–73. http://dx.doi.org/10.1002/ange.200503814.

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34

Paquette, Leo A., William R. S. Barton, and Judith C. Gallucci. "Synthesis of 1-Aza-8-thiabicyclo[4.2.1]nona-2,4-diene 8,8-Dioxide and Its Conversion to a Strained Spirocycle via Photoinduced SO2−N Bond Cleavage." Organic Letters 6, no. 8 (April 2004): 1313–15. http://dx.doi.org/10.1021/ol049679s.

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35

Herbig, Marcus, Henrik Scholz, Uwe Böhme, Betty Günther, Lia Gevorgyan, Daniela Gerlach, Jörg Wagler, Sandra Schwarzer, and Edwin Kroke. "New cyclic and spirocyclic aminosilanes." Main Group Metal Chemistry 44, no. 1 (January 1, 2021): 51–72. http://dx.doi.org/10.1515/mgmc-2021-0007.

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Abstract New cyclic and spirocyclic aminosilanes were synthesised using ethylenediamine, 2-aminobenzylamine, 1,8-diaminonaphthalene, o-phenylenediamine, and trans-cyclohexane-1,2-diamine as starting material. These diamines were converted into aminosilanes using silicon tetrachloride and dimethyldichlorosilane directly and via the N,N’-bis(trimethylsilylated) amino derivatives. 15 new compounds of the type (diamino)(SiMe3)2, (diamino)2Si, (diamino)SiMe2, and (diamino)SiCl2 have been prepared. The formation of two cyclotrisilazane derivatives was observed starting from (N,N’-2-aminobenzylamino)dichlorosilane by trimerisation. All synthesised compounds have been characterised with NMR-, Raman-, or IR-spectroscopy, mass-spectrometry, and boiling or melting point. Single-crystal X-ray structure analyses of several derivatives have been performed. The degree of substitution with trimethylsilyl groups in the final compounds depends on the ring size of the spirocycles. It was shown with quantum chemical calculations on the M062X/6-31G(d) level that trimethylsilyl groups have a stabilising effect on 5-membered ring systems and a destabilising effect on 6-membered rings in these compounds.

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36

Kotha, Sambasivarao, Kakali Lahiri, and Gaddamedi Sreevani. "Design and Synthesis of Aromatics through [2+2+2] Cyclotrimerization." Synlett 29, no. 18 (August 8, 2018): 2342–61. http://dx.doi.org/10.1055/s-0037-1609584.

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The [2+2+2] cycloaddition reaction is a useful tool to realize unusual chemical transformations which are not achievable by traditional methods. Here, we report our work during the past two decades that involve utilization of transition-metal complexes in a [2+2+2] cyclotrimerization reaction. Several key “building blocks” were assembled by a [2+2+2] cycloaddition approach and they have been further expanded by other synthetic transformations to design unusual amino acids and peptides, diphenylalkanes, bis- and trisaryl benzene derivatives, annulated benzocycloalkanes, spirocycles, and spirooxindole derivatives. Furthermore, we have also discussed about alkyne surrogates, environmentally friendly, and stereoselective [2+2+2] cycloaddition reactions. Application of the [2+2+2] cycloaddition reaction in total synthesis is also covered. In this review we also included others work to give a balanced view of the recent developments in the area of [2+2+2] cycloaddition.1 Introduction2 Unusual Amino Acids and Peptides3 Heteroanalogues of Indane4 Diphenylalkane Derivatives5 Multi-Armed Aryl Benzene Derivatives6 Annulated Benzocycloalkanes7 Spirocycles8 Selectivity in [2+2+2] Cycloaddition of Alkynes9 [2+2+2] Cycloaddition Reactions under Environmentally Friendly Conditions10 Alkyne Surrogates11 Domino Reactions involving a [2+2+2] Cycloaddition12 Biologically Important Targets/Total Synthesis13 Conclusions

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37

Fan, Peng, Tian-Tian Liu, Hong-Yu Qu, Peng Tao, Chun-Xia Liu, Xiao-Qian Liu, Mei-Hua Shen, Xiaoguang Bao, and Hua-Dong Xu. "Intramolecular Alder-ene cycloisomerization of cyclopropenes with alkenes to access spirocycles." Organic Chemistry Frontiers 8, no. 17 (2021): 4799–804. http://dx.doi.org/10.1039/d1qo00299f.

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38

Freeman, Jared L., Freda F. Li, Daniel P. Furkert, and Margaret A. Brimble. "Synthetic Studies Towards Spirocyclic Imine Marine Toxins Using N-Acyl Iminium Ions as Dienophiles in Diels–Alder Reactions." Synlett 31, no. 07 (February 13, 2020): 657–71. http://dx.doi.org/10.1055/s-0039-1691593.

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Cyclic imine marine toxins have attracted considerable attention from the synthetic community in the past two decades due to their unique chemical structures and clinically relevant biological activities. This review presents recent efforts of our group in the development of various strategies to efficiently construct the common spirocyclic imine fragments of the cyclic imine toxins. In particular, the use of α,β-unsaturated N-acyl iminium ion dienophiles in Diels–Alder reactions are highlighted, whereby direct access to spirocyclic imine motifs was obtained and important mechanistic details were discovered. Alternative approaches to spirocyclic imine systems involving hydroamination of amino alkynes are also summarized. One such approach led to serendipitous access to N-vinyl amide products, while our most recently reported approach involving an intermolecular Diels–Alder/cross-coupling sequence using novel 2-bromo-1,3-butadienes to access 5,6-spirocyclic imines is also discussed. Additionally, the development of a novel method to construct another challenging motif present in the portimines is also introduced.1 Introduction2 Strategies towards the Spirocyclic Imine Fragment of Cyclic Imine Toxins2.1 Diels–Alder Cycloadditions of α,β-Unsaturated N-Acyl Iminium Dienophiles2.2 Early Studies Using in situ-Generated Iminium Ion Dienophiles2.3 Use of More Stable Iminium Ion Dienophiles for Diels–Alder Reactions2.4 Other Notable Strategies towards Spirocyclic Imines2.5 Recent Efforts towards the 5,6-Spirocyclic Imine Marine Toxin Portimine A2.6 Construction of Another Challenging Motif of Portimine A3 Conclusion and Future Perspectives

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39

Chupakhin, Evgeny, Olga Babich, Alexander Prosekov, Lyudmila Asyakina, and Mikhail Krasavin. "Spirocyclic Motifs in Natural Products." Molecules 24, no. 22 (November 17, 2019): 4165. http://dx.doi.org/10.3390/molecules24224165.

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Spirocyclic motifs are emerging privileged structures for drug discovery. They are also omnipresent in the natural products domain. However, until today, no attempt to analyze the structural diversity of various spirocyclic motifs occurring in natural products and their relative populations with unique compounds reported in the literature has been undertaken. This review aims to fill that void and analyze the diversity of structurally unique natural products containing spirocyclic moieties of various sizes.

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40

Fan, Lulu, Shinobu Takizawa, Yoshiki Takeuchi, Kazuhiro Takenaka, and Hiroaki Sasai. "Pd-catalyzed enantioselective intramolecular α-arylation of α-substituted cyclic ketones: facile synthesis of functionalized chiral spirobicycles." Organic & Biomolecular Chemistry 13, no. 17 (2015): 4837–40. http://dx.doi.org/10.1039/c5ob00382b.

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Synthesis of chiral spirocyclic ketones was accomplishedviathe Pd-catalyzed intramolecular α-arylation of α-substituted cyclic ketones. The obtained spirocyclic ketone could be converted into an acid–base organocatalyst.

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41

Livendahl, M., J. Jamroskovic, M. Hedenström, T. Görlich, N. Sabouri, and E. Chorell. "Synthesis of phenanthridine spiropyrans and studies of their effects on G-quadruplex DNA." Organic & Biomolecular Chemistry 15, no. 15 (2017): 3265–75. http://dx.doi.org/10.1039/c7ob00300e.

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Zhang, Ye, Tian-Lu Zheng, Fu Cheng, Kun-Long Dai, Kun Zhang, Ai-Jun Ma, Fu-Min Zhang, Xiao-Ming Zhang, Shao-Hua Wang, and Yong-Qiang Tu. "Facile access to diverse all-carbon quaternary center containing spirobicycles by exploring a tandem Castro–Stephens coupling/acyloxy shift/cyclization/semipinacol rearrangement sequence." Chemical Science 11, no. 15 (2020): 3878–84. http://dx.doi.org/10.1039/d0sc00102c.

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Verrier, Charlie, Sylvie Moebs-Sanchez, Yves Queneau, and Florence Popowycz. "The Piancatelli reaction and its variants: recent applications to high added-value chemicals and biomass valorization." Organic & Biomolecular Chemistry 16, no. 5 (2018): 676–87. http://dx.doi.org/10.1039/c7ob02962d.

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Han, Xi, Lingheng Kong, Jiami Feng, and Xingwei Li. "Rhodium(iii)-catalyzed synthesis of spirocyclic isoindole N-oxides and isobenzofuranones via C–H activation and spiroannulation." Chemical Communications 56, no. 41 (2020): 5528–31. http://dx.doi.org/10.1039/d0cc00830c.

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Smith, Laura K., and Ian R. Baxendale. "Total syntheses of natural products containing spirocarbocycles." Organic & Biomolecular Chemistry 13, no. 39 (2015): 9907–33. http://dx.doi.org/10.1039/c5ob01524c.

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Tan, Bojun, Long Liu, Huayu Zheng, Tianyi Cheng, Dianhu Zhu, Xiaofeng Yang, and Xinjun Luan. "Two-in-one strategy for fluorene-based spirocycles via Pd(0)-catalyzed spiroannulation of o-iodobiaryls with bromonaphthols." Chemical Science 11, no. 37 (2020): 10198–203. http://dx.doi.org/10.1039/d0sc04386a.

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Chen, Shi Peng, Jian Ting Zhang, Gao Peng Wang, Cheng Lin Zhu, Jun Min Feng, Xiao Ji Wang, and Shuang Ping Huang. "A Prophase Study on the Concise Synthesis of Aculeatin A." Advanced Materials Research 881-883 (January 2014): 461–64. http://dx.doi.org/10.4028/www.scientific.net/amr.881-883.461.

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The 1,7-dioxadispiro [5.1.5.-pentadecane spirocyclic architecture is the main structural feature in the aculeatins which attracted scientists interesting for the remarkably high cytotoxicity, anti-bacterial and anti-protozoal activities. A prophase study on concise synthesis of the core 1,7-dioxadispiro [5.1.5.-pentadecane spirocyclic architecture of aculeatins was accomplished by using Mukaiyama aldol reaction.

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Ueda, Mitsuhiro, Yoshitaka Uenoyama, Nozomi Terasoma, Shoko Doi, Shoji Kobayashi, Ilhyong Ryu, and John A. Murphy. "A construction of 4,4-spirocyclic γ-lactams by tandem radical cyclization with carbon monoxide." Beilstein Journal of Organic Chemistry 9 (July 5, 2013): 1340–45. http://dx.doi.org/10.3762/bjoc.9.151.

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A straightforward synthesis of 4,4-spirocyclic indol γ-lactams by tandem radical cyclization of iodoaryl allyl azides with CO was achieved. The reaction of iodoaryl allyl azides, TTMSS and AIBN under CO pressure (80 atm) in THF at 80 °C gave the desired 4,4-spirocyclic indoline, benzofuran, and oxindole γ-lactams in moderate to good yields.

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Yadav, J. S., B. V. Subba Reddy, V. Hari Krishna, T. Swamy, and GG KS Narayana Kumar. "Iodine-promoted Prins-cyclization of ketones — A facile synthesis of spirocyclic-4-iodo-tetrahydropyrans and 5,6-dihydro-2H-pyrans." Canadian Journal of Chemistry 85, no. 6 (June 1, 2007): 412–15. http://dx.doi.org/10.1139/v07-048.

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Homoallylic and homopropargylic alcohols undergo smooth coupling with ketones in the presence of molecular iodine at ambient temperature to produce spirocyclic-4-iodotetrahydropyrans and 5,6-dihydro-2H-pyrans, respectively, in high yields in a short reaction time with high selectivity. The use of molecular iodine makes this procedure quite simple, more convenient, and cost-effective.Key words: Prins-cyclization, iodine, homopropargylic alcohol, spirocyclic-4-iodopyrans.

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Weidmann, Verena, Mathias Schaffrath, Holger Zorn, Julia Rehbein, and Wolfgang Maison. "Elucidation of the regio- and chemoselectivity of enzymatic allylic oxidations with Pleurotus sapidus – conversion of selected spirocyclic terpenoids and computational analysis." Beilstein Journal of Organic Chemistry 9 (October 29, 2013): 2233–41. http://dx.doi.org/10.3762/bjoc.9.262.

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Allylic oxidations of olefins to enones allow the efficient synthesis of value-added products from simple olefinic precursors like terpenes or terpenoids. Biocatalytic variants have a large potential for industrial applications, particularly in the pharmaceutical and food industry. Herein we report efficient biocatalytic allylic oxidations of spirocyclic terpenoids by a lyophilisate of the edible fungus Pleurotus sapidus. This ‘’mushroom catalysis’’ is operationally simple and allows the conversion of various unsaturated spirocyclic terpenoids. A number of new spirocyclic enones have thus been obtained with good regio- and chemoselectivity and chiral separation protocols for enantiomeric mixtures have been developed. The oxidations follow a radical mechanism and the regioselectivity of the reaction is mainly determined by bond-dissociation energies of the available allylic CH-bonds and steric accessibility of the oxidation site.

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