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Journal articles on the topic 'Indole alkaloids; Substitution reactions'

Author: Grafiati

Published: 4 June 2021

Last updated: 16 February 2022

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1

Sariöz, Ö., та M. I. Abdullah. "Electrophilic substitution reactions of indole alkaloids with α,β-unsaturated carbonyl compounds in the presence of K10 montmorillonite". Russian Journal of Organic Chemistry 42, № 6 (2006): 879–82. http://dx.doi.org/10.1134/s107042800606011x.

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2

Nagaraju, Karre, and Dawei Ma. "Oxidative coupling strategies for the synthesis of indole alkaloids." Chemical Society Reviews 47, no. 21 (2018): 8018–29. http://dx.doi.org/10.1039/c8cs00305j.

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3

Partsvaniya, D. A., R. N. Akhvlediani, V. E. Zhigachev, E. N. Gordeev, L. N. Kuleshova, and N. N. Suvorov. "Indole derivatives. 129. Electrophilic-substitution reactions in 4,5-ethylenedioxyindole." Chemistry of Heterocyclic Compounds 23, no. 7 (1987): 755–57. http://dx.doi.org/10.1007/bf00475642.

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4

Somei, Masanori, Fumio Yamada, and Daisuke Shinmyo. "Nucleophilic Substitution Reactions on Indole Nucleus: Syntheses of 2-Substituted Indole-3-carboxaldehydes." HETEROCYCLES 38, no. 2 (1994): 273. http://dx.doi.org/10.3987/com-93-6599.

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5

Dittami, James P., and Halasya Ramanathan. "Intramolecular radical cyclization reactions. An approach to the indole alkaloids." Tetrahedron Letters 29, no. 1 (1988): 45–48. http://dx.doi.org/10.1016/0040-4039(88)80012-1.

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6

Blechert, Siegfried, Ruth Knier, Harald Schroers, and Thomas Wirth. "Domino Reactions - New Concepts in the Synthesis of Indole Alkaloids and Other Polycyclic Indole Derivatives." Synthesis 1995, no. 05 (1995): 592–604. http://dx.doi.org/10.1055/s-1995-3950.

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7

Song, Jin, Dian-Feng Chen, and Liu-Zhu Gong. "Recent progress in organocatalytic asymmetric total syntheses of complex indole alkaloids." National Science Review 4, no. 3 (2017): 381–96. http://dx.doi.org/10.1093/nsr/nwx028.

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Abstract Indole and its structural analogues have been frequently found in numerous alkaloids, pharmaceutical products and related materials. The enantioselective construction of these structures allows efficient total synthesis of optically pure indole alkaloids, and hence has received worldwide interest. In the past decade, asymmetric organocatalysis has been recognized as one of the most powerful strategies to create chiral molecules with high levels of stereoselectivity. In particular, organocatalytic asymmetric cascade reactions often occur with multiple bond-breaking and forming events s

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8

Ohno, Hiroaki, and Shinsuke Inuki. "Nonbiomimetic total synthesis of indole alkaloids using alkyne-based strategies." Organic & Biomolecular Chemistry 19, no. 16 (2021): 3551–68. http://dx.doi.org/10.1039/d0ob02577a.

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Significance of nonbiomimetic natural product synthesis and nonbiomimetic total syntheses of indole alkaloids based on the construction of core structures using alkyne reactions are summarized in this review.

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9

Liu, Yun-Lin, Guo-Shu Chen, and Xiao-Tong Lin. "3-(2-Isocyanoethyl)indole: A Versatile Reagent for Polycyclic Spiroindoline Synthesis." Synlett 31, no. 11 (2020): 1033–39. http://dx.doi.org/10.1055/s-0039-1690853.

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Polycyclic spiroindolines are the basic skeletons of large families of indole alkaloids that exhibit a broad spectrum of biological and pharmacological activities. The past seven years have seen impressive developments in the construction of polycyclic spiroindolines enabled by 3-(2-isocyanoethyl)indole-based cascade reactions. We herein give a brief summary on this evolution and highlight our contributions in this field.1 Introduction2 Cascade Reactions Involving Nitrilium Ion Intermediates3 Cascade Reactions Involving Ketenimine Intermediates4 Conclusion and Outlook

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10

Pritchett, Beau P., and Brian M. Stoltz. "Enantioselective palladium-catalyzed allylic alkylation reactions in the synthesis of Aspidosperma and structurally related monoterpene indole alkaloids." Natural Product Reports 35, no. 6 (2018): 559–74. http://dx.doi.org/10.1039/c7np00069c.

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11

BLECHERT, S., R. KNIER, H. SCHROERS, and T. WIRTH. "ChemInform Abstract: Domino Reactions - New Concepts in the Synthesis of Indole Alkaloids and Other Polycyclic Indole Derivatives." ChemInform 26, no. 48 (2010): no. http://dx.doi.org/10.1002/chin.199548280.

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12

Shi, Bao-Bao, Jing-Song Lu, Jing Wu, Mei-Fen Bao, and Xiang-Hai Cai. "Symmetric cytotoxic trimeric and dimeric indole alkaloids isolated from Bousigonia angustifolia." Organic Chemistry Frontiers 8, no. 11 (2021): 2601–7. http://dx.doi.org/10.1039/d0qo01565b.

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Symmetric trimeric and dimeric indole alkaloids were isolated for the first time from Bousigonia angustifolia, and they could be constructed through Friedel–Crafts and free radical reactions, respectively.

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13

Khan, Irfan, Shahnawaz Khan, Vikas Tyagi, Pradeep Singh Chouhan та Prem M. S. Chauhan. "Diversity-oriented reconstruction of primitive diketopiperazine-fused tetrahydro-β-carboline ring systems via Pictet–Spengler/Ugi-4CR/deprotection-cyclization reactions". RSC Advances 5, № 124 (2015): 102713–22. http://dx.doi.org/10.1039/c5ra17259d.

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14

Avula, Bharathi, Satyanarayanaraju Sagi, Yan-Hong Wang, et al. "Identification and Characterization of Indole and Oxindole Alkaloids from Leaves of Mitragyna speciosa Korth Using Liquid Chromatography–Accurate QToF Mass Spectrometry." Journal of AOAC INTERNATIONAL 98, no. 1 (2015): 13–21. http://dx.doi.org/10.5740/jaoacint.14-110.

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Abstract Alkaloids have been reported to be the major physiologically active constituents in Mitragyna. An analytical method was developed to provide an alternative, fast method for characterization of alkaloids from various M. speciosa samples. The separation was achieved using an RP octylsilyl (C8) column, MS detection, and a water–acetonitrile with formic acid gradient as the mobile phase. Ultra-HPLC/quadrupole time-of-flight MS analysis and characterization were performed on 12 corynanthe-type indole/oxindole alkaloids obtainedfrom the leaves of M. speciosa Korth. The indoles and oxindoles

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15

Somei, Masanori, Toshiya Kawasaki, Yoshikazu Fukui, et al. "The Chemistry of 1-Hydroxyindole Derivatives: Nucleophilic Substitution Reactions on Indole Nucleus." HETEROCYCLES 34, no. 10 (1992): 1877. http://dx.doi.org/10.3987/com-92-6140.

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16

Wang, Yu, Matti J. P. Vaismaa, Kari Rissanen, and Robert Franzén. "N1-Functionalized Indole-Phosphane Oxazoline (IndPHOX) Ligands in Asymmetric Allylic Substitution Reactions." European Journal of Organic Chemistry 2012, no. 8 (2012): 1569–76. http://dx.doi.org/10.1002/ejoc.201101540.

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17

Chikvaidze, I. Sh, �. A. Mumladze, Sh A. Samsoniya, L. N. Kurkovskaya, Dzh A. Kereselidze, and N. N. Suvorov. "Bisindoles 29. Electrophilic substitution reactions in the 2,5?-bis-1h-indole series." Chemistry of Heterocyclic Compounds 28, no. 10 (1992): 1135–40. http://dx.doi.org/10.1007/bf00529574.

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18

Marino, Joseph P., Min Woo Kim, and Ross Lawrence. "Reactions of indole sulfoxides with dichloroketene: a new approach to the physostigmine alkaloids." Journal of Organic Chemistry 54, no. 8 (1989): 1782–84. http://dx.doi.org/10.1021/jo00269a004.

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19

Koreňová, Anna, Alžbeta Krutošíková, Jaroslav Kováč, and Stanislav Celec. "Synthesis and reactions of furo[3,2-c]pyridine derivatives." Collection of Czechoslovak Chemical Communications 52, no. 1 (1987): 192–98. http://dx.doi.org/10.1135/cccc19870192.

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The synthesis of a new type of condensed heterocycle pyrido[3',4':4,5]furo[3,2-b]indole (V) and 1,2,4-triazolo[4'',3'':1',2']pyrido[3',4':4,5]furo[3,2-b]indoles (IX) is described and the substitution nucleophilic reaction with 2-(2-nitrophenyl)-4-chlorofuro[3,2-c]pyridine (X) is presented.

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20

Shchekotikhin, A. E., E. P. Baberkina, V. N. Buyanov, K. F. Turchin, and N. N. Suvorov. "Naphthoindoles. 8. Electrophilic substitution reactions of 4,11-dimethyxynaphtho[2,3-f]indole-5,10-dione." Chemistry of Heterocyclic Compounds 34, no. 7 (1998): 813–15. http://dx.doi.org/10.1007/bf02251688.

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21

Li, Can, Hong-Hao Zhang, Tao Fan, Yang Shen, Qiong Wu, and Feng Shi. "Brønsted acid-catalyzed regioselective reactions of 2-indolylmethanols with cyclic enaminone and anhydride leading to C3-functionalized indole derivatives." Organic & Biomolecular Chemistry 14, no. 29 (2016): 6932–36. http://dx.doi.org/10.1039/c6ob01282e.

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An abnormal regioselective substitution of 2-indolylmethanols with nucleophiles has been established to afford C3-functionalized indole derivatives in high yield and regiospecificity (40 examples, up to 99% yield).

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22

Serdyuk, Olga, Igor Trushkov, Maxim Uchuskin, and Vladimir Abaev. "Indolylvinyl Ketones: Building Blocks for the Synthesis of Natural Products and Bioactive Compounds." Synthesis 51, no. 04 (2019): 787–815. http://dx.doi.org/10.1055/s-0037-1611702.

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Indolylvinyl ketones are valuable building blocks that can be utilized for the synthesis of numerous natural products and bioactive molecules containing an indole core motif. Herein, we describe their application for the total synthesis of some alkaloids, their analogues, and a variety of other important compounds, with an emphasis on biologically active examples.1 Introduction2 Functionalization of the Enone C=C Bond2.1 Reduction2.2 Michael Addition2.3 Cycloaddition3 Transformation of the Carbonyl Group3.1 Reduction3.2 Knoevenagel Reaction3.3 Addition of Organometallic Compounds3.4 Olefinatio

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23

Martin, Stephen F., Brigitte Benage, Sidney A. Williamson, and Stephen P. Brown. "Applications of the intramolecular diels-alder reactions of heterodienes to the syntheses of indole alkaloids." Tetrahedron 42, no. 11 (1986): 2903–10. http://dx.doi.org/10.1016/s0040-4020(01)90579-4.

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24

Liang, Kangjiang, and Chengfeng Xia. "Recent Advances of Transition Metal-Mediated Oxidative Radical Reactions in Total Synthesis of Indole Alkaloids." Chinese Journal of Chemistry 35, no. 3 (2017): 255–70. http://dx.doi.org/10.1002/cjoc.201600777.

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25

Li, Jie Jack. "ChemInform Abstract: Applications of Radical Cyclization Reactions in Total Syntheses of Naturally Occurring Indole Alkaloids." ChemInform 33, no. 36 (2010): no. http://dx.doi.org/10.1002/chin.200236269.

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26

Coyle, Robert, Patrick McArdle, and Fawaz Aldabbagh. "Tandem Reactions via Barton Esters with Intermolecular Addition and Vinyl Radical Substitution onto Indole." Journal of Organic Chemistry 79, no. 12 (2014): 5903–7. http://dx.doi.org/10.1021/jo5008543.

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27

Wang, Yu, Matti J. P. Vaismaa, Kari Rissanen, and Robert Franzen. "ChemInform Abstract: N1-Functionalized Indole-Phosphane Oxazoline (IndPHOX) Ligands in Asymmetric Allylic Substitution Reactions." ChemInform 43, no. 30 (2012): no. http://dx.doi.org/10.1002/chin.201230100.

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28

YAMADA, F., D. SHINMYO, and M. SOMEI. "ChemInform Abstract: The Chemistry of Indoles. Part 68. Nucleophilic Substitution Reactions on Indole Nucleus: Syntheses of 2-Substituted Indole-3-carboxaldehydes." ChemInform 25, no. 26 (2010): no. http://dx.doi.org/10.1002/chin.199426138.

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29

CHIKVAIDZE, I. SH, E. A. MUMLADZE, SH A. SAMSONIYA, L. N. KURKOVSKAYA, DZH A. KERESELIDZE, and N. N. SUVOROV. "ChemInform Abstract: Biindoles. Part 29. Electrophilic Substitution Reactions in the 2,5′- Bi-1H-indole Series." ChemInform 24, no. 45 (2010): no. http://dx.doi.org/10.1002/chin.199345193.

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30

Banerji, J., U. Dutta, B. Basak, M. Saha, H. Budzikiewicz, and A. Chatterjee. "ChemInform Abstract: Electrophilic Substitution Reactions of Indole. Part 20. Use of Montmorillonite Clay K-10." ChemInform 33, no. 6 (2010): no. http://dx.doi.org/10.1002/chin.200206125.

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31

Fochi, Mariafrancesca, Luca Bernardi, and Lorenzo Caruana. "Enantioselective Approaches to 3,4-Annulated Indoles Using Organocatalytic Domino Reactions." Synlett 28, no. 13 (2017): 1530–43. http://dx.doi.org/10.1055/s-0036-1589494.

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Organocatalytic domino reactions of 4-substituted indoles are summarized in this account. Two reactions have been developed, one with enals, activated by secondary amine catalysts via iminium ions, and one with nitroethene, using a phosphoric acid catalyst. Both reactions required solving the challenge posed by the very low nucleophilicity of the indole substrates, which bear an electron-withdrawing Michael acceptor at C4. DFT calculations were used to shed light on the unique reaction pathway followed by the phosphoric acid catalyzed transformation, wherein a bicoordinated nitronic acid inte

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32

Hasaninejad, Alireza, Abdolkarim Zare, Hashem Sharghi, et al. "A solvent-free protocol for facile condensation of indoles with carbonyl compounds using silica chloride as a new, highly efficient, and mild catalyst." Canadian Journal of Chemistry 85, no. 6 (2007): 416–20. http://dx.doi.org/10.1139/v07-051.

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A simple and efficient solvent-free procedure for the preparation of bis(indolyl)methanes via electrophilic substitution reactions of indoles with aldehydes and ketones is described. The reactions took place in the presence of a catalytic amount of silica chloride at room temperature. The advantages of this method are high yields, short reaction times, low cost, and compliance with green-chemistry protocols.Key words: silica chloride, indole, carbonyl compound, solvent-free, bis(indolyl)methane.

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33

Beemelmanns, Christine, Steffen Gross, and Hans-Ulrich Reissig. "ChemInform Abstract: Towards the Core Structure of Strychnos Alkaloids Using Samarium Diiodide-Induced Reactions of Indole Derivatives." ChemInform 45, no. 22 (2014): no. http://dx.doi.org/10.1002/chin.201422166.

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34

SHCHEKOTIKHIN, A. E., E. P. BABERKINA, V. N. BYANOV, K. F. TURCHIN, and N. N. SUVOROV. "ChemInform Abstract: Naphthoindoles. Part 8. Electrophilic Substitution Reactions of 4,11-Dimethoxynaphtho[2,3-f]indole-5,10-dione." ChemInform 30, no. 2 (2010): no. http://dx.doi.org/10.1002/chin.199902117.

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35

Coyle, Robert, Patrick McArdle, and Fawaz Aldabbagh. "ChemInform Abstract: Tandem Reactions via Barton Esters with Intermolecular Addition and Vinyl Radical Substitution onto Indole." ChemInform 45, no. 51 (2014): no. http://dx.doi.org/10.1002/chin.201451134.

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36

Kranke, Birgit, and Horst Kunz. "Stereoselective synthesis of chiral piperidine derivatives employing arabinopyranosylamine as the carbohydrate auxiliary." Canadian Journal of Chemistry 84, no. 4 (2006): 625–41. http://dx.doi.org/10.1139/v06-060.

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Stereoselective synthesis of 2-substituted dehydropiperidinones and their further transformation to variously disubstituted piperidine derivatives was achieved employing D-arabinopyranosylamine as the stereodifferentiating carbohydrate auxiliary. A domino MannichMichael reaction of 1-methoxy-3-(trimethylsiloxy)butadiene (Danishefsky's diene) with O-pivaloylated arbinosylaldimines furnished N-arabinosyl dehydropiperidinones in high diastereoselectivity. Subsequent conjugate cuprate addition gave 2,6-cis-substituted piperidinones, while enolate alkylation furnished 2,3-trans-substituted dehydro

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37

Mayer, Szabolcs, András Keglevich, Csilla Sepsey Für, et al. "Results in Chemistry of Natural Organic Compounds. Synthesis of New Anticancer Vinca Alkaloids and Flavone Alkaloids." Chemistry 2, no. 3 (2020): 714–26. http://dx.doi.org/10.3390/chemistry2030046.

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The antitumor indole–indoline alkaloids of the evergreen Catharanthus roseus—namely vinblastine and vincristine—are widely used in chemotherapy of cancer. Many efforts were made to synthesize more efficient derivatives with less side-effect. The 14,15-cyclopropane derivative of vinblastine was synthesized successfully by a five-step procedure starting from vindoline. Vincristine, vinorelbine and several derivatives condensed with a cyclopropane ring were synthesized. Various hybrid molecules were prepared by the coupling reaction of vindoline and methyl ester of tryptophan, which were conjugat

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38

Cadar, Emin, Aneta Tomescu, Cristina Luiza Erimia, Alef Mustafa, and Rodica Sîrbu. "The Impact of Alkaloids Structures from NaturalCompounds on Public Health." European Journal of Social Sciences Education and Research 5, no. 1 (2015): 34. http://dx.doi.org/10.26417/ejser.v5i1.p34-39.

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Alkaloids are organic heterocycle substances with nitrogen, of plant origin, with basic character, arising from the secondary metabolism of plants, which give characteristic reactions and exert an effect on animal bodies, most often of a toxic nature. Alkaloids have at least one atom of heterocycle nitrogen, in which case it is often tertiary, less frequently quaternary. The heterocycles can condense among themselves or with other cycles in such a way that alkaloid molecules may become poly- or macro-cycles. Alkaloids are classified on both the criterion of chemical structure, as well as based

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39

Kuo, Fu-Ming, Ming-Chung Tseng, Ya-Hew Yen, and Yen-Ho Chu. "Microwave accelerated Pictet–Spengler reactions of tryptophan with ketones directed toward the preparation of 1,1-disubstituted indole alkaloids." Tetrahedron 60, no. 52 (2004): 12075–84. http://dx.doi.org/10.1016/j.tet.2004.10.025.

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40

Olyaei, Abolfazl, Mohsen Vaziri, Reza Razeghi, Shams Bahareh, and Hasan Bagheri. "Novel approach to bis(indolyl)methanes using nickel nanoparticles as a reusable catalyst under solvent-free conditions." Journal of the Serbian Chemical Society 78, no. 4 (2013): 463–68. http://dx.doi.org/10.2298/jsc120506076o.

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A nanosized Nickel as catalyst has been developed for the electrophilic substitution reactions of indole with variousaromatic aldehydes under solvent-free conditions to afford the corresponding bis(indolyl)methanes in high to excellent yields. The described method has promising features such as no hazardous organic solvents or catalysts, short reaction time, high product yields, simple work-up procedure, reusable catalyst and easy product separation without further purification with column chromatography.

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41

Kirschke, K., A. Möller, E. Schmitz, R. J. Kuban, and B. Schulz. "Surprising reactions or special azoolefins - self-arylation, indole ring closure, mild chlorine substitution, and “tert. amino effect”." Tetrahedron Letters 27, no. 36 (1986): 4281–84. http://dx.doi.org/10.1016/s0040-4039(00)94252-7.

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42

Crawford, Sarah M., Craig A. Wheaton, Vinayak Mishra, and Mark Stradiotto. "Probing the effect of donor-fragment substitution in Mor-DalPhos on palladium-catalyzed C–N and C–C cross-coupling reactivity." Canadian Journal of Chemistry 96, no. 6 (2018): 578–86. http://dx.doi.org/10.1139/cjc-2017-0749.

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The competitive catalytic screening of 18 known and newly prepared Mor-DalPhos ligand variants in the palladium-catalyzed cross-coupling of chlorobenzene with aniline, octylamine, morpholine, indole, ammonia, or acetone is presented, including ligands derived from the new secondary phosphine HP(Me2Ad)2 (Me2Ad = 3,5-dimethyladamantyl). Although triarylphosphine ancillary ligand variants performed poorly in these test reactions, ligands featuring either PAd2 or P(Me2Ad)2 donors (Ad = 1-adamantyl) gave rise to superior catalytic performance. Multiple Mor-DalPhos variants proved effective in cross

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43

Pan, Xiaohong, та Thomas D. Bannister. "Sequential Sonagashira and Larock Indole Synthesis Reactions in a General Strategy To Prepare Biologically Active β-Carboline-Containing Alkaloids". Organic Letters 16, № 23 (2014): 6124–27. http://dx.doi.org/10.1021/ol5029783.

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44

Kraľovičová, Eva, Alžbeta Krutošíková, and Jaroslav Kováč. "Preparation and reactions of thieno[3,2-b]furan derivatives." Collection of Czechoslovak Chemical Communications 51, no. 8 (1986): 1685–91. http://dx.doi.org/10.1135/cccc19861685.

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Reactions of 3-(5-aryl-2-furyl)propenoic, 3-(2-benzo[b]furyl)propenoic and 3-(5-ethoxycarbonyl-4H-furo[3,2-b]-2-pyrrolyl)propenoic acids with thionyl chloride in the presence of triethylbenzylammonium chloride were investigated. The obtained 2-arylthieno[3,2-b]-furan-5-carboxylic acid chlorides Ia - Ic and 3-chlorothieno[3,2-b]benzo[b]furan-2-carboxylic acid chloride afforded in substitution nucleophilic reactions the corresponding esters V and carboxylic acids VI which were decarboxylated to VII. 3-Chlorothieno[3,2-b]benzo[b]furan-2-carboxylic acid chloride (Id), 6-ethoxycarbonyl-3-chlorothie

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45

LOMADZE, N. SH, I. SH CHIKVAIDZE, N. L. TARGAMADZE, L. N. KURKOVSKAYA, SH A. SAMSONIYA, and N. N. SUVOROV. "ChemInform Abstract: Pyrroloindoles. Part 16. Some Electrophilic Substitution Reactions of 2,7-Diethoxycarbonyl-1H,6H-pyrrolo(2,3-e)indole." ChemInform 26, no. 25 (2010): no. http://dx.doi.org/10.1002/chin.199525122.

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46

Mori, Miwako, Masato Nakanishi, Daisuke Kajishima, and Yoshihiro Sato. "A Novel and General Synthetic Pathway to Strychnos Indole Alkaloids: Total Syntheses of (−)-Tubifoline, (−)-Dehydrotubifoline, and (−)-Strychnine Using Palladium-Catalyzed Asymmetric Allylic Substitution." Journal of the American Chemical Society 125, no. 32 (2003): 9801–7. http://dx.doi.org/10.1021/ja029382u.

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47

Brown, Dearg S., Philippe Charreau, Thomas Hansson, and Steven V. Ley. "Substitution reactions of 2-phenylsulphonyl-piperidines and -pyrrolidines with carbon nucleophiles: Synthesis of the pyrrolidine alkaloids norruspoline and ruspolinone." Tetrahedron 47, no. 7 (1991): 1311–28. http://dx.doi.org/10.1016/s0040-4020(01)86388-2.

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48

Pan, Xiaohong, та Thomas D. Bannister. "ChemInform Abstract: Sequential Sonagashira and Larock Indole Synthesis Reactions in a General Strategy to Prepare Biologically Active β-Carboline-Containing Alkaloids." ChemInform 46, № 20 (2015): no. http://dx.doi.org/10.1002/chin.201520260.

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49

Mentzel, Uffe V., David Tanner, and Janne E. Tønder. "Comparative Study of the Kumada, Negishi, Stille, and Suzuki−Miyaura Reactions in the Synthesis of the Indole Alkaloids Hippadine and Pratosine." Journal of Organic Chemistry 71, no. 15 (2006): 5807–10. http://dx.doi.org/10.1021/jo060729b.

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50

SOMEI, M., T. KAWASAKI, Y. FUKUI, et al. "ChemInform Abstract: The Chemistry of Indoles. Part 61. The Chemistry of 1-Hydroxyindole Derivatives: Nucleophilic Substitution Reactions on Indole Nucleus." ChemInform 24, no. 6 (2010): no. http://dx.doi.org/10.1002/chin.199306148.

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