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Journal articles on the topic 'Taiwaniaquinoid'

Author: Grafiati

Published: 20 February 2023

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1

Graham, Marlowe, Robert W. Baker, and Christopher S. P. McErlean. "Cationic Polyene Cyclization for Taiwaniaquinoid Construction." European Journal of Organic Chemistry 2017, no. 4 (2017): 908–13. http://dx.doi.org/10.1002/ejoc.201601349.

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2

Guardia, Juan J., Antonio Fernández, José Justicia, et al. "Unprecedented Elimination Reactions of Cyclic Aldols: A New Biosynthetic Pathway toward the Taiwaniaquinoid Skeleton." Molecules 28, no. 4 (2023): 1524. http://dx.doi.org/10.3390/molecules28041524.

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The acid treatment of 6,7-seco-abietane dialdehydes gives, in high yield, the corresponding derivatives with the 4a-methyltetrahydrofluorene skeleton of taiwaniaquinoids. A mechanism involving the elimination of formic acid from the cyclic aldol intermediate is proposed here. This process can be postulated as a new biogenetic pathway from abietane diterpenes to taiwaniaquinoids. Using this novel reaction, the first enantiospecific synthesis of bioactive natural cupresol and taxodal has been obtained.

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3

Meng, Yonggang, Yizhen Liu, Zhigang Lv, et al. "Concise Synthesis of Taiwaniaquinol B and 5-epi-Taiwaniaquinone G." Natural Product Communications 10, no. 12 (2015): 1934578X1501001. http://dx.doi.org/10.1177/1934578x1501001204.

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The natural product taiwaniaquinol B and the unnatural 5- epi-taiwaniaquinone G were synthesized based on a highly efficient tandem acylation–Nazarov cyclization approach to build the tricyclic skeleton.

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4

Kakde, Badrinath N., Pooja Kumari, and Alakesh Bisai. "Total Synthesis of (±)-Taiwaniaquinol F and Related Taiwaniaquinoids." Journal of Organic Chemistry 80, no. 20 (2015): 9889–99. http://dx.doi.org/10.1021/acs.joc.5b01345.

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5

Ramírez-Macías, Inmaculada, Clotilde Marín, Hakima Es-Samti, et al. "Taiwaniaquinoid and abietane quinone derivatives with trypanocidal activity against T. cruzi and Leishmania spp." Parasitology International 61, no. 3 (2012): 405–13. http://dx.doi.org/10.1016/j.parint.2012.02.001.

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6

Kakde, Badrinath N., Pooja Kumari, and Alakesh Bisai. "ChemInform Abstract: Total Synthesis of (.+-.)-Taiwaniaquinol F and Related Taiwaniaquinoids." ChemInform 47, no. 10 (2016): no. http://dx.doi.org/10.1002/chin.201610207.

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7

Alvarez-Manzaneda, Enrique, Rachid Chahboun, Eduardo Cabrera, et al. "An enantiospecific route towards taiwaniaquinoids. First synthesis of (−)-taiwaniaquinone H and (−)-dichroanone." Organic & Biomolecular Chemistry 7, no. 24 (2009): 5146. http://dx.doi.org/10.1039/b916209g.

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8

Majetich, George, and Joel M. Shimkus. "Concise syntheses of (±)-dichroanone, (±)-dichroanal B, (±)-taiwaniaquinol B, and (±)-taiwaniaquinone D." Tetrahedron Letters 50, no. 26 (2009): 3311–13. http://dx.doi.org/10.1016/j.tetlet.2009.02.074.

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9

Alvarez-Manzaneda, Enrique, Rachid Chahboun, Eduardo Cabrera та ін. "A thermal 6π electrocyclization strategy towards taiwaniaquinoids. First enantiospecific synthesis of (−)-taiwaniaquinone G". Chem. Commun., № 5 (2009): 592–94. http://dx.doi.org/10.1039/b816812a.

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10

Thommen, Christophe, Chandan Kumar Jana, Markus Neuburger, and Karl Gademann. "Syntheses of Taiwaniaquinone F and Taiwaniaquinol A via an Unusual Remote C–H Functionalization." Organic Letters 15, no. 6 (2013): 1390–93. http://dx.doi.org/10.1021/ol4003652.

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11

Jana, Chandan Kumar, Rosario Scopelliti, and Karl Gademann. "A Synthetic Entry into the Taiwaniaquinoids Based on a Biogenetic Hypothesis: Total Synthesis of (−)-Taiwaniaquinone H." Chemistry - A European Journal 16, no. 26 (2010): 7692–95. http://dx.doi.org/10.1002/chem.201001085.

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12

Ozeki, Minoru, Megumi Satake, Toshinori Toizume, et al. "First asymmetric total synthesis of (+)-taiwaniaquinol D and (−)-taiwaniaquinone D by using intramolecular Heck reaction." Tetrahedron 69, no. 19 (2013): 3841–46. http://dx.doi.org/10.1016/j.tet.2013.03.051.

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13

Jana, Chandan Kumar, Rosario Scopelliti, and Karl Gademann. "ChemInform Abstract: A Synthetic Entry into the Taiwaniaquinoids Based on a Biogenetic Hypothesis: Total Synthesis of (-)-Taiwaniaquinone H." ChemInform 41, no. 50 (2010): no. http://dx.doi.org/10.1002/chin.201050183.

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14

Kakde, Badrinath N., Amarchand Parida, Pooja Kumari, and Alakesh Bisai. "Total syntheses of (±)-taiwaniaquinol D and (±)-taiwaniaquinone D via a key Lewis acid-catalyzed Nazarov type cyclization." Tetrahedron Letters 57, no. 29 (2016): 3179–84. http://dx.doi.org/10.1016/j.tetlet.2016.06.030.

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15

Liao, Xuebin, Levi M. Stanley та John F. Hartwig. "Enantioselective Total Syntheses of (−)-Taiwaniaquinone H and (−)-Taiwaniaquinol B by Iridium-Catalyzed Borylation and Palladium-Catalyzed Asymmetric α-Arylation". Journal of the American Chemical Society 133, № 7 (2011): 2088–91. http://dx.doi.org/10.1021/ja110215b.

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16

Trauner, D., G. Liang, Y. Xu, and I. Seiple. "Synthesis of Taiwaniaquinoids." Synfacts 2007, no. 2 (2007): 0126. http://dx.doi.org/10.1055/s-2006-955768.

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17

Majetich, George, and Joel M. Shimkus. "The Taiwaniaquinoids: A Review†‡." Journal of Natural Products 73, no. 2 (2010): 284–98. http://dx.doi.org/10.1021/np9004695.

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18

Liao, Xuebin, Levi M. Stanley та John F. Hartwig. "ChemInform Abstract: Enantioselective Total Syntheses of (-)-Taiwaniaquinone H (I) and (-)-Taiwaniaquinol B (II) by Iridium-Catalyzed Borylation and Palladium-Catalyzed Asymmetric α-Arylation." ChemInform 42, № 27 (2011): no. http://dx.doi.org/10.1002/chin.201127191.

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19

Rodger, Robert T., Marlowe S. Graham, and Christopher S. P. McErlean. "Hyperconjomer stereocontrol of cationic polyene cyclisations." Organic & Biomolecular Chemistry 17, no. 37 (2019): 8551–60. http://dx.doi.org/10.1039/c9ob01364d.

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The stereochemical outcome of cationic polyene cyclisations of geranylbenzene derivatives is affected by the different reactivity of hyperconjomer intermediates. The synthesis of (±)-taiwaniaquinone G by a cationic polyene cyclisation is described.

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20

Liang, Guangxin, Yue Xu, Ian B. Seiple, and Dirk Trauner. "Synthesis of Taiwaniaquinoids via Nazarov Triflation." Journal of the American Chemical Society 128, no. 34 (2006): 11022–23. http://dx.doi.org/10.1021/ja062505g.

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21

Graham, Marlowe S., and Christopher S. P. McErlean. "Total Synthesis of Taiwaniaquinoids: A Strategic Account." Asian Journal of Organic Chemistry 10, no. 9 (2021): 2274–86. http://dx.doi.org/10.1002/ajoc.202100303.

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22

Wang, Jinqian, Jing Wang, Changwei Li, et al. "Synthesis of 5-epi-Taiwaniaquinone G." Journal of Organic Chemistry 79, no. 13 (2014): 6354–59. http://dx.doi.org/10.1021/jo500931e.

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23

Katakawa, Kazuaki. "Syntheses of Taiwaniaquinoids Based on Hypothetical Biogenetic Routes." Journal of Synthetic Organic Chemistry, Japan 72, no. 3 (2014): 305–6. http://dx.doi.org/10.5059/yukigoseikyokaishi.72.305.

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24

Bisai, Vishnumaya, Aditi Gupta, and Alakesh Bisai. "Naturally occurring taiwaniaquinoids: biosynthetic relationships and synthetic approaches." Arkivoc 2018, no. 6 (2018): 57–84. http://dx.doi.org/10.24820/ark.5550190.p010.631.

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25

Guardia, Juan J., Rubén Tapia, Soumicha Mahdjour, et al. "Antiproliferative Activity of Natural Taiwaniaquinoids and Related Compounds." Journal of Natural Products 80, no. 2 (2017): 308–18. http://dx.doi.org/10.1021/acs.jnatprod.6b00700.

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26

Shockley, Samantha E., Jeffrey C. Holder, and Brian M. Stoltz. "A Catalytic, Enantioselective Formal Synthesis of (+)-Dichroanone and (+)-Taiwaniaquinone H." Organic Letters 16, no. 24 (2014): 6362–65. http://dx.doi.org/10.1021/ol5031537.

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27

Li, Liang-Qun, Ming-Ming Li, Dong Chen, et al. "Catalytic asymmetric formal total synthesis of (+)-dichroanone and (+)-taiwaniaquinone H." Tetrahedron Letters 55, no. 43 (2014): 5960–62. http://dx.doi.org/10.1016/j.tetlet.2014.08.110.

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28

Ren, Ting, Lijiao Zhang, Jinqian Wang, Chuanjun Song, Ruiyong Wang, and Junbiao Chang. "Study on the interaction of taiwaniaquinoids with FTO by spectroscopy and molecular modeling." Journal of Biomolecular Structure and Dynamics 35, no. 14 (2016): 3182–93. http://dx.doi.org/10.1080/07391102.2016.1249957.

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29

Li, Shuoliang, and Pauline Chiu. "Acid-promoted sequential cationic cyclizations for the synthesis of (±)-taiwaniaquinol B." Tetrahedron Letters 49, no. 11 (2008): 1741–44. http://dx.doi.org/10.1016/j.tetlet.2008.01.084.

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30

Tapia, Rubén, Juan J. Guardia, Esteban Alvarez, et al. "General Access to Taiwaniaquinoids Based on a Hypothetical Abietane C7–C8 Cleavage Biogenetic Pathway." Journal of Organic Chemistry 77, no. 1 (2011): 573–84. http://dx.doi.org/10.1021/jo202163y.

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31

Kakde, Badrinath N., Subhadip De, Dhananjay Dey, and Alakesh Bisai. "Metal triflate-catalyzed cyclization of arylvinylcarbinols: formal synthesis of (±)-dichroanone and (±)-taiwaniaquinone H." RSC Advances 3, no. 22 (2013): 8176. http://dx.doi.org/10.1039/c3ra41497c.

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32

Deng, Jun, Ruofan Li, Yijie Luo, et al. "Divergent Total Synthesis of Taiwaniaquinones A and F and Taiwaniaquinols B and D." Organic Letters 15, no. 8 (2013): 2022–25. http://dx.doi.org/10.1021/ol400717h.

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33

Li, Liang-Qun, Ming-Ming Li, Dong Chen, et al. "ChemInform Abstract: Catalytic Asymmetric Formal Total Synthesis of (+)-Dichroanone (Ia) and (+)-Taiwaniaquinone H (Ib)." ChemInform 46, no. 17 (2015): no. http://dx.doi.org/10.1002/chin.201517254.

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34

Kakde, Badrinath N., Amarchand Parida, Nivesh Kumar, Abhishek Mourya, and Alakesh Bisai. "FeCl3-Catalyzed Highly Efficient Nazarov Type Cyclization of Arylvinylcarbinols: Total Synthesis of (±)-Dichroanal B and Related Taiwaniaquinoids†." ChemistrySelect 1, no. 12 (2016): 3357–62. http://dx.doi.org/10.1002/slct.201600890.

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35

Alvarez-Manzaneda, Enrique, Rachid Chahboun, Eduardo Cabrera, et al. "A Very Efficient Route toward the 4a-Methyltetrahydrofluorene Skeleton: Short Synthesis of (±)-Dichroanone and (±)-Taiwaniaquinone H." Journal of Organic Chemistry 74, no. 9 (2009): 3384–88. http://dx.doi.org/10.1021/jo900153y.

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36

Yan, Xiuxiang, та Xiangdong Hu. "Protecting-Group-Free Synthesis of Taiwaniaquinone H Using a One-Pot Thermal Ring Expansion/4π-Electrocyclization Strategy". Journal of Organic Chemistry 79, № 11 (2014): 5282–86. http://dx.doi.org/10.1021/jo5008652.

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37

Fillion, Eric, та Dan Fishlock. "Total Synthesis of (±)-Taiwaniaquinol B via a Domino Intramolecular Friedel−Crafts Acylation/Carbonyl α-tert-Alkylation Reaction". Journal of the American Chemical Society 127, № 38 (2005): 13144–45. http://dx.doi.org/10.1021/ja054447p.

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38

Alvarez-Manzaneda, Enrique, Rachid Chahboun, Eduardo Cabrera, et al. "Correction to A Very Efficient Route toward the 4a-Methyltetrahydrofluorene Skeleton: Short Synthesis of (±)-Dichroanone and (±)-Taiwaniaquinone H." Journal of Organic Chemistry 74, no. 16 (2009): 6414. http://dx.doi.org/10.1021/jo901501h.

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39

Tang, Shouchu, Yanfen Xu, Jinmei He, et al. "Application of a Domino Friedel−Crafts Acylation/Alkylation Reaction to the Formal Syntheses of (±)-Taiwaniaquinol B and (±)-Dichroanone." Organic Letters 10, no. 9 (2008): 1855–58. http://dx.doi.org/10.1021/ol800513v.

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40

Yan, Xiuxiang, та Xiangdong Hu. "ChemInform Abstract: Protecting-Group-Free Synthesis of Taiwaniaquinone H Using a One-Pot Thermal Ring Expansion/4π-Electrocyclization Strategy." ChemInform 45, № 47 (2014): no. http://dx.doi.org/10.1002/chin.201447222.

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41

Banerjee, Mainak, Ranjan Mukhopadhyay, Basudeb Achari, and Asish Kr Banerjee. "General Route to 4a-Methylhydrofluorene Diterpenoids: Total Syntheses of (±)-Taiwaniaquinones D and H, (±)-Taiwaniaquinol B, (±)-Dichroanal B, and (±)-Dichroanone." Journal of Organic Chemistry 71, no. 7 (2006): 2787–96. http://dx.doi.org/10.1021/jo052589w.

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42

Wang, Ning, Xinxin Han, Junya Li, et al. "Influence of the methyl position on the binding of 5-epi-taiwaniaquinone G to HHb investigated by spectrofluorimetry and molecular modelling." Physics and Chemistry of Liquids 57, no. 4 (2018): 516–27. http://dx.doi.org/10.1080/00319104.2018.1491573.

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43

Li, Zhigang, Jinqian Wang, Ting Ren, et al. "Influence of the methyl position on the binding of 5-epi-taiwaniaquinone G to HSA investigated by spectrofluorimetry and molecular modeling." Medicinal Chemistry Research 25, no. 5 (2016): 1009–19. http://dx.doi.org/10.1007/s00044-016-1547-5.

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44

Singh, Ritesh, Maloy Kumar Parai, and Gautam Panda. "Application of Nazarov cyclization to access [6-5-6] and [6-5-5]tricyclic core embedded new heterocycles: an easy entry to structures related to Taiwaniaquinoids." Organic & Biomolecular Chemistry 7, no. 9 (2009): 1858. http://dx.doi.org/10.1039/b901632e.

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45

Singh, Ritesh, and Gautam Panda. "Application of Nazarov type electrocyclization to access [6,5,6] and [6,5,5] core embedded new polycycles: an easy entry to tetrahydrofluorene scaffolds related to Taiwaniaquinoids and C-nor-D homosteroids." Organic & Biomolecular Chemistry 9, no. 13 (2011): 4782. http://dx.doi.org/10.1039/c0ob00892c.

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46

Singh, Ritesh, and Gautam Panda. "ChemInform Abstract: Application of Nazarov Type Electrocyclization to Access [6,5,6] and [6,5,5] Core Embedded New Polycycles: An Easy Entry to Tetrahydrofluorene Scaffolds Related to Taiwaniaquinoids and C-nor-D Homosteroids." ChemInform 42, no. 48 (2011): no. http://dx.doi.org/10.1002/chin.201148029.

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47

Kakde, Badrinath N., Amarchand Parida, Vipin R. Gavit, Rhituparna Nandi, Sourav Kundu, and Alakesh Bisai. "FeCl3-Catalyzed Highly Efficient Nazarov Type Cyclization of Arylvinyl Carbinols: Total Syntheses of Naturally Occurring Taiwaniaquinoids." Prayogik Rasayan 5, no. 2 (2021). http://dx.doi.org/10.53023/p.rasayan-20211115.

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FeCl3-catalyzed cyclization of arylvinylcarbinols for the synthesis of [6,5,6]-carbotricyclic core sharing an all-carbon quaternary center has been described in this full article. A careful mechanistic details suggest that the reaction follows a stepwise mechanism via the intermediacy of arylallyl carbocationic species. The carbocation subsequently reacts with an adjacent aromatic ring to form [6,5,6]-carbotricyclic scaffold of abeo-abietane diterpenoids. The methodology works under mild conditions to afford a variety of carbotricyclic core in good to excellent yields (up to 99% yield). Our st

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48

"Syntheses of Taiwaniaquinone F and Taiwaniaquinol A." Synfacts 9, no. 06 (2013): 0587. http://dx.doi.org/10.1055/s-0033-1338716.

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49

Alvarez-Manzaneda, Enrique, Rachid Chahboun, Eduardo Cabrera та ін. "ChemInform Abstract: A Thermal 6π Electrocyclization Strategy Towards Taiwaniaquinoids. First Enantiospecific Synthesis of (-)-Taiwaniaquinone G." ChemInform 40, № 25 (2009). http://dx.doi.org/10.1002/chin.200925174.

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50

Wang, Jinqian, Jing Wang, Changwei Li, et al. "ChemInform Abstract: Synthesis of 5-epi-Taiwaniaquinone G." ChemInform 46, no. 1 (2015). http://dx.doi.org/10.1002/chin.201501202.

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