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Journal articles on the topic 'Regioselective reduction'

Author: Grafiati

Published: 23 November 2024

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1

Butler, Christopher R., Justin Bendesky, and Allen Milton Schoffstall. "Regioselective Reduction of 1H-1,2,3-Triazole Diesters." Molecules 26, no. 18 (September 15, 2021): 5589. http://dx.doi.org/10.3390/molecules26185589.

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Regioselective reactions can play pivotal roles in synthetic organic chemistry. The reduction of several 1-substituted 1,2,3-triazole 4,5-diesters by sodium borohydride has been found to be regioselective, with the C(5) ester groups being more reactive towards reduction than the C(4) ester groups. The amount of sodium borohydride and reaction time required for reduction varied greatly depending on the N(1)-substituent. The presence of a β-hydroxyl group on the N(1)-substituent was seen to have a rate enhancing effect on the reduction of the C(5) ester group. The regioselective reduction was attributed to the lower electron densities of the C(5) and the C(5) ester carbonyl carbon of the 1,2,3-triazole, which were further lowered in cases involving intramolecular hydrogen bonding.

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2

Hussaini, Syed Raziullah, and Mark G. Moloney. "Regioselective Reduction of β‐Enaminoesters." Synthetic Communications 35, no. 8 (April 1, 2005): 1129–34. http://dx.doi.org/10.1081/scc-200054223.

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3

Hirota, Kosaku, Hironao Sajiki, Ryuji Hattori, Yasunari Monguchi, Genzoh Tanabe, and Osamu Muraoka. "Regioselective BH3–hydride reduction of inosine derivatives." Tetrahedron Letters 43, no. 4 (January 2002): 653–55. http://dx.doi.org/10.1016/s0040-4039(01)02209-2.

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4

Bruhn, Torsten, and Christian Brückner. "Origin of the Regioselective Reduction of Chlorins." Journal of Organic Chemistry 80, no. 10 (March 6, 2015): 4861–68. http://dx.doi.org/10.1021/acs.joc.5b00137.

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5

Setamdideh, Davood, and Behzad Zeynizadeh. "Mild and Convenient Method for Reduction of Carbonyl Compounds with the NaBH4/Charcoal System in Wet THF." Zeitschrift für Naturforschung B 61, no. 10 (October 1, 2006): 1275–81. http://dx.doi.org/10.1515/znb-2006-1014.

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The NaBH4/C (charcoal) system reduces a variety of carbonyl compounds such as aldehydes, ketones, acyloins and α-diketones to their corresponding alcohols in high to excellent yields. Reduction reactions were carried out in wet THF at r. t. In addition, regioselective 1,2-reduction of α,β - unsaturated aldehydes and ketones was achieved perfectly with this reducing system. By decreasing the amount of aprotic solvent, all reductions took place fast and efficiently under solid-gel condition

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6

Katagiri, Takayuki, and Yutaka Amao. "Visible light driven selective NADH regeneration using a system of water-soluble zinc porphyrin and homogeneous polymer-dispersed rhodium nanoparticles." New Journal of Chemistry 45, no. 35 (2021): 15748–52. http://dx.doi.org/10.1039/d1nj02856a.

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We discovered the catalytic activity of Rh nanoparticles dispersed by polyvinylpyrrolidone for regioselective NAD+ reduction to 1,4-NADH. Only 1,4-NADH was produced as the reduction product of NAD+ with visible-light irradiation.

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7

Nguyen, Mai, Issam Kherbouche, Sarra Gam-Derouich, Iman Ragheb, Stéphanie Lau-Truong, Aazdine Lamouri, Georges Lévi, et al. "Regioselective surface functionalization of lithographically designed gold nanorods by plasmon-mediated reduction of aryl diazonium salts." Chem. Commun. 53, no. 82 (2017): 11364–67. http://dx.doi.org/10.1039/c7cc05974d.

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8

Ishii, Hideki, Sergei V. Dzyuba, and Koji Nakanishi. "Lactone-free ginkgolides via regioselective DIBAL-H reduction." Organic & Biomolecular Chemistry 3, no. 19 (2005): 3471. http://dx.doi.org/10.1039/b509129b.

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9

Davey, C. "Regioselective reduction of substituted dinitroarenes using baker's yeast." Tetrahedron Letters 35, no. 41 (October 10, 1994): 7867–70. http://dx.doi.org/10.1016/s0040-4039(00)77393-x.

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10

Davey, Claire L., Lawson W. Powell, Nicholas J. Turner, and Andrew Wells. "Regioselective reduction of substituted dinitroarenes using baker's yeast." Tetrahedron Letters 35, no. 42 (October 1994): 7867–70. http://dx.doi.org/10.1016/0040-4039(94)80139-8.

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11

Tanwar, Babita, Priyank Purohit, Banothu Naga Raju, Dinesh Kumar, Damodara N. Kommi, and Asit K. Chakraborti. "An “all-water” strategy for regiocontrolled synthesis of 2-aryl quinoxalines." RSC Advances 5, no. 16 (2015): 11873–83. http://dx.doi.org/10.1039/c4ra16568c.

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12

Stachel, Hans-Dietrich, Josef Schachtner, and Josef Seidel. "Reduktion cyclischer Maleinsäurederivate/Reduction of Cyclic Maleic Acid Derivatives." Zeitschrift für Naturforschung B 51, no. 3 (March 1, 1996): 409–16. http://dx.doi.org/10.1515/znb-1996-0317.

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Abstract A series of potentially cytotoxic α,β-unsaturated γ -hydroxy-butyrolactones, -lactams and -thiolactones has been synthesized via regioselective hydride reduction of the appropriate maleic acid anhydrides, imides and thioanhydrides. By this means a straightforward access to naturally occurring antibiotic narthigenine 2, its hitherto unknown thio-analogue 5b and higher substituted derivatives and analogues of 2 is presented.

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13

Li, Jide, Weiping Tang, Demin Ren, Jiaxi Xu, and Zhanhui Yang. "Iridium-catalysed highly selective reduction–elimination of steroidal 4-en-3-ones to 3,5-dienes in water." Green Chemistry 21, no. 8 (2019): 2088–94. http://dx.doi.org/10.1039/c9gc00654k.

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14

Liu, Hsing-Jang, and Weide Luo. "Synthetic applications of glycidic thiolesters. Regioselective reduction to 1,3-diols and 2,3-epoxy alcohols." Canadian Journal of Chemistry 70, no. 1 (January 1, 1992): 128–34. http://dx.doi.org/10.1139/v92-022.

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Glycidic thiolesters were shown to undergo regioselective reduction with Raney nickel to give 1,3-diols. With sodium borohydride at room temperature and lithium aluminum hydride at −78 °C, the reduction of glycidic thiolesters was found to proceed chemoselectively to furnish 2,3-epoxy alcohols. Keywords: glycidic thiolesters, reduction, 1,3-diols, 2,3-epoxy alcohols.

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15

Devaux, Jean-François, Steven V. O'Neil, Nathalie Guillo, and Leo A. Paquette. "Studies Toward an Asymmetric Synthesis of CP-263,114 and CP-225,917." Collection of Czechoslovak Chemical Communications 65, no. 4 (2000): 490–510. http://dx.doi.org/10.1135/cccc20000490.

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An enantioselective approach to construction of the complex framework of the CP compounds is presented. The synthesis relies on initial elaboration of the two sidechains. The "upper" appendage was asymmetrically dihydroxylated with both AD-mix reagents in order to lend flexibility to the scheme and provide the necessary handle for evolving the additional stereogenic centers. These fragments were linked to benzoic acid via Birch reduction-alkylation and subsequent cuprate addition. A series of functionalization reactions including dissolving metal reduction, Claisen rearrangement, iodolactonization, regioselective epoxide cleavage-oxidation, and intramolecular Wadsworth-Emmons cyclization took advantage of highly efficient stereocontrol. However, this flexibility was thwarted when deprotonation of a penultimate intermediate failed to be regioselective in the proper direction.

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16

Tan, Minghui, Guohui Yang, Tiejun Wang, Tharapong Vitidsant, Jie Li, Qinhong Wei, Peipei Ai, Mingbo Wu, Jingtang Zheng, and Noritatsu Tsubaki. "Active and regioselective rhodium catalyst supported on reduced graphene oxide for 1-hexene hydroformylation." Catalysis Science & Technology 6, no. 4 (2016): 1162–72. http://dx.doi.org/10.1039/c5cy01355k.

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17

Gates, Ashley M., and Webster L. Santos. "Regioselective Diboron-Mediated Semireduction of Terminal Allenes." Synthesis 51, no. 24 (October 10, 2019): 4619–24. http://dx.doi.org/10.1055/s-0039-1690207.

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A method for the regioselective reduction of the terminal double bond of 1,1-disubstituted allenes has been developed. In the presence of a palladium catalyst, tetrahydroxydiboron and stoichiometric water, allene semireduction proceeds in high yield to afford Z-alkenes selectively.

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18

Tassano, Erika, Kemal Merusic, Isa Buljubasic, Olivia Laggner, Tamara Reiter, Andreas Vogel, and Mélanie Hall. "Regioselective biocatalytic self-sufficient Tishchenko-type reaction via formal intramolecular hydride transfer." Chemical Communications 56, no. 47 (2020): 6340–43. http://dx.doi.org/10.1039/d0cc02509g.

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Alcohol dehydrogenases catalyze the regioselective lactonization of dialdehydes via a bio-Tishchenko-like reaction. The nicotinamide-dependent self-sufficient reduction–oxidation sequence proceeds through a formal intramolecular hydride shift.

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19

Cheng, Hsiu-Yi, Chong-Si Sun, and Duen-Ren Hou. "Regioselective Palladium-Catalyzed Formate Reduction ofN-Heterocyclic Allylic Acetates." Journal of Organic Chemistry 72, no. 7 (March 2007): 2674–77. http://dx.doi.org/10.1021/jo0624896.

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20

Milewska, Maria J., Tomasz Bytner, and Tadeusz Połoński. "Synthesis of Lactams by Regioselective Reduction of Cyclic Dicarboximides." Synthesis 1996, no. 12 (December 1996): 1485–88. http://dx.doi.org/10.1055/s-1996-4405.

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21

Keglevich, Györg, Zsolt Böcskei, Kálmán Újszászy, and László Tőke. "Synthesis of 1,2,3,6-Tetrahydrophosphorin 1-Oxides by Regioselective Reduction." Synthesis 1997, no. 12 (December 1997): 1391–93. http://dx.doi.org/10.1055/s-1997-1364.

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22

Denislamova, E. S., N. V. Bubnov, and A. N. Maslivets. "Regioselective reduction of 1H-pyrrole-2,3-diones with thioacetamide." Russian Journal of Organic Chemistry 49, no. 2 (February 2013): 312. http://dx.doi.org/10.1134/s107042801302022x.

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23

Battisti, Umberto M., Giuseppe Cannazza, Marina M. Carrozzo, Daniela Braghiroli, Carlo Parenti, Francesca Rosato, and Luigino Troisi. "Regioselective reduction of 3-substituted 2,3-dihydrobenzothiadiazines with borohydrides." Tetrahedron Letters 51, no. 33 (August 2010): 4433–36. http://dx.doi.org/10.1016/j.tetlet.2010.06.081.

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24

Jumde, Varsha R., Niek N. H. M. Eisink, Martin D. Witte, and Adriaan J. Minnaard. "C3 Epimerization of Glucose, via Regioselective Oxidation and Reduction." Journal of Organic Chemistry 81, no. 22 (October 28, 2016): 11439–43. http://dx.doi.org/10.1021/acs.joc.6b02074.

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25

Nomura, Kota, Tadashi Mizoguchi, and Hitoshi Tamiaki. "Regioselective Reduction Pathway of Geranylgeranyl Moiety in Chlorophyll Biosynthesis." Biophysical Journal 106, no. 2 (January 2014): 182a—183a. http://dx.doi.org/10.1016/j.bpj.2013.11.1032.

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26

Civitello, Edgar R., and Henry Rapoport. "The regioselective cleavage of aryl tosylates by electrochemical reduction." Journal of Organic Chemistry 57, no. 3 (January 1992): 834–40. http://dx.doi.org/10.1021/jo00029a010.

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27

Hirota, Kosaku, Hironao Sajiki, Ryuji Hattori, Yasunari Monguchi, Genzoh Tanabe, and Osamu Muraoka. "ChemInform Abstract: Regioselective BH3-Hydride Reduction of Inosine Derivatives." ChemInform 33, no. 16 (May 22, 2010): no. http://dx.doi.org/10.1002/chin.200216204.

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28

Hagiwara, Hisahiro, Naomi Honma, Kimihiko Kinugawa, Shota Sato, Takashi Hoshi, and Toshio Suzuki. "Second Generation Synthesis of the Neo-Clerodane Diterpenoid Methyl Barbascoate." Natural Product Communications 8, no. 7 (July 2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800706.

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The second generation total synthesis of the neo-clerodane diterpenoid, methyl barbascoate, was accomplished in seven or nine linear steps via double enol triflation and subsequent palladium catalyzed double carbonylation, followed by regioselective samarium diiodide mediated conjugate reduction.

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29

Kazmia, Syed Najam-ul-Hussain, Zaheer Ahmed, Abdul Malik, Nighat Afza, and Wolfgang Voelterc. "A Regioselective One Pot Synthesis and Synthetic Applications of Cyanodeoxy Sugars by Cyanotrimethylsilane." Zeitschrift für Naturforschung B 50, no. 2 (February 1, 1995): 294–302. http://dx.doi.org/10.1515/znb-1995-0225.

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The regioselective epoxide opening of different 2,3-anhydropyranoses by cyanotrimethylsilane is investigated. The isolated cyanodeoxy pyranoses allow easy access to the corresponding branched-chains aminomethyl sugars by lithium aluminium hydride reduction or sugar amides by controlled acid hydrolysis.

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30

Liu, Huiyuan, Yujiang Song, Shushuang Li, Jia Li, Yuan Liu, Ying-Bing Jiang, and Xinwen Guo. "Synthesis of core/shell structured Pd3Au@Pt/C with enhanced electrocatalytic activity by regioselective atomic layer deposition combined with a wet chemical method." RSC Advances 6, no. 71 (2016): 66712–20. http://dx.doi.org/10.1039/c6ra04990g.

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Core/shell structured Pd₃Au@Pt/C created by regioselective atomic layer deposition combined with a wet chemical method demonstrates improved electrocatalytic activity toward formic acid oxidation and oxygen reduction compared with commercial Pt/C.

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31

Wang, Jia-Yin, Guigen Li, Wen-Juan Hao, and Bo Jiang. "Enantio- and Regioselective CuH-Catalyzed Conjugate Reduction of Yne–Allenones." Organic Letters 23, no. 10 (May 6, 2021): 3828–33. http://dx.doi.org/10.1021/acs.orglett.1c00892.

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32

Zhang, Bing, Xueying Guo, Lei Tao, Ruolin Li, Zhenyang Lin, and Wanxiang Zhao. "Rhodium-Catalyzed Regioselective and Chemoselective Deoxygenative Reduction of 1,3-Diketones." ACS Catalysis 12, no. 8 (April 5, 2022): 4640–47. http://dx.doi.org/10.1021/acscatal.2c00520.

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33

Nishizawa, Mugio, Hisaya Nishide, Kaoru Kuriyama, and Yuji Hayashi. "Regioselective reduction of .ALPHA.,.GAMMA.-onoceradienedione : Synthesis of lansiolic acid." CHEMICAL & PHARMACEUTICAL BULLETIN 34, no. 10 (1986): 4443–46. http://dx.doi.org/10.1248/cpb.34.4443.

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34

Hunter, Roger, and Birgit Bartels. "The first solvent-directed regioselective ketal reduction of unsymmetrical glycols." Journal of the Chemical Society, Perkin Transactions 1, no. 11 (1991): 2887. http://dx.doi.org/10.1039/p19910002887.

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35

Dragovich, Peter S., Thomas J. Prins, and Ru Zhou. "Palladium Catalyzed, Regioselective Reduction of 1,2-Epoxides by Ammonium Formate." Journal of Organic Chemistry 60, no. 15 (July 1995): 4922–24. http://dx.doi.org/10.1021/jo00120a042.

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36

Brestensky, Donna M., and Jeffrey M. Stryker. "Regioselective conjugate reduction and reductive silylation of α,β-unsaturated." Tetrahedron Letters 30, no. 42 (January 1989): 5677–80. http://dx.doi.org/10.1016/s0040-4039(00)76168-5.

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37

Dotsenko, V. V., and S. G. Krivokolysko. "Regioselective reduction of 2-cyanoprop-2-enethioamides with sodium borohydride." Russian Chemical Bulletin 61, no. 12 (December 2012): 2261–64. http://dx.doi.org/10.1007/s11172-012-0321-1.

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38

Nakamura, Kaoru, Shin-ichi Kondo, Yasushi Kawai, Kouichi Hida, Kazutada Kitano, and Atsuyoshi Ohno. "Enantio- and regioselective reduction of α-diketones by baker's yeast." Tetrahedron: Asymmetry 7, no. 2 (February 1996): 409–12. http://dx.doi.org/10.1016/0957-4166(96)00020-1.

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39

Epling, Gary A., and Qingxi Wang. "Regioselective reduction of epoxides by electron transfer—a photochemical approach." J. Chem. Soc., Chem. Commun., no. 16 (1992): 1133–34. http://dx.doi.org/10.1039/c39920001133.

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40

Lee, Sun-Hwa, Dmitry V. Gutsulyak, and Georgii I. Nikonov. "Chemo- and Regioselective Catalytic Reduction of N-Heterocycles by Silane." Organometallics 32, no. 16 (June 17, 2013): 4457–64. http://dx.doi.org/10.1021/om400269q.

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41

Yamaji, Ayaka, Hayato Tsurugi, Yoshihiro Miyake, Kazushi Mashima, and Hiroshi Shinokubo. "Chemo- and Regioselective Reduction of 5,15-Diazaporphyrins Providing Antiaromatic Azaporphyrinoids." Chemistry - A European Journal 22, no. 12 (February 3, 2016): 3956–61. http://dx.doi.org/10.1002/chem.201600066.

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42

Ishitsuka, Takuya, Yasuhiro Okuda, Robert K. Szilagyi, Seiji Mori, and Yasushi Nishihara. "The molecular mechanism of palladium-catalysed cyanoesterification of methyl cyanoformate onto norbornene." Dalton Transactions 45, no. 18 (2016): 7786–93. http://dx.doi.org/10.1039/c6dt00341a.

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Density functional theory-based potential energy surface investigation revealed that the reaction mechanism of palladium-catalysed cyanoesterification onto norbornene (NBE) proceeds through exclusive exo-coordination, regioselective olefin insertion first into the Pd–COOR bond, and reduction elimination to form the subsituted NBE.

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43

Hosoda, Ryusuke, Yoshiyuki Horio, Kei Shimoda, Manabu Hamada, Hatsuyuki Hamada, and Hiroki Hamada. "Regioselective Hydroxylation and Glucosylation of Flavanones with Cultured Plant Cells of Eucalyptus perriniana." Natural Product Communications 8, no. 7 (July 2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800712.

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Cultured plant cells of Eucalyptus perriniana catalyzed reduction regioselective hydroxylation and regioselective glycosylation of flavanones. (2 S)-Flavanone was converted into (2 S)-flavan-4-ol (2 S)-flavan-4,7-diol (2 S)-flavan-7-ol (2 S)-flavan-7-yl glucoside and (2 S)-flavan-7-yl gentiobioside. The cells glucosylated (2 S)-flavan-6-ol to (2 S)-flavan-6-yl glucoside. (2 S)-Flavan-2′-ol was transformed to (2 S)-flavan-2′,4-diol (2 S)-flavan-2′,7-diol (2 S)-flavan-2′-yl glucoside. In addition (2 S)-flavan-4′-ol was transformed to (2 S)-flavan-4,4′-diol (2 S)-flavan-4′,7-diol (2 S)-flavan-4′-yl glucoside.

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44

Liu, Jun, Zhi-Bing Dong, Caizhu Chang, Jialin Geng, Yinxin Liu, and Yuguo Du. "Stereoselective Total Synthesis of Arundinolides A and B." Synthesis 52, no. 10 (February 5, 2020): 1576–84. http://dx.doi.org/10.1055/s-0039-1691699.

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The efficient and enantioselective syntheses of arundinolides A and B have been accomplished for the first time from chiral pool methyl-2,3-O-isopropylidene-β-d-ribofuranoside and d-ethyl lactate. The key features of the total synthesis are intramolecular crotonyl migration and NaBH4-CuCl catalyzed regioselective reduction and cross-metathesis reaction.

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45

Zhang, Miaomiao, Hongmei Jiao, Haojie Ma, Ran Li, Bo Han, Yuqi Zhang, and Jijiang Wang. "Zn-Catalyzed Regioselective and Chemoselective Reduction of Aldehydes, Ketones and Imines." International Journal of Molecular Sciences 23, no. 20 (October 21, 2022): 12679. http://dx.doi.org/10.3390/ijms232012679.

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An operationally convenient Zn-catalyzed synthesis of alcohols by the reduction of aldehydes, ketones, and α,β-unsaturated aldehydes/ketones is reported. It is a rare example of using mild and sustainable HBpin as a reductant for catalytic reduction of carbonyl compounds in the absence of acid or base as hydrolysis reagent. The reaction is upscalable and proceeds in high selectivity without the formation of boronate ester by-products, and tolerates sensitive functionalities, such as iodo, bromo, chloro, fluoro, nitro, trifluoromethyl, aminomethyl, alkynyl, and amide. The Zn(OAc)2/HBpin combination has been also proved to be chemoselective for the C=N reduction of imine analogs.

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46

Khlebnikova, T. S., V. G. Isakova, A. V. Baranovskii, and F. A. Lakhvich. "Regioselective reduction of 2-perfluoroalkanoylcyclohexane-1,3-diones and their enamino derivatives." Russian Journal of General Chemistry 81, no. 4 (April 2011): 672–79. http://dx.doi.org/10.1134/s1070363211040098.

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47

Debenham, Sheryl D., and Eric J. Toone. "Regioselective reduction of 4,6-O-benzylidenes using triethylsilane and BF3·Et2O." Tetrahedron: Asymmetry 11, no. 2 (February 2000): 385–87. http://dx.doi.org/10.1016/s0957-4166(99)00584-4.

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48

Link, J. T., and Samuel J. Danishefsky. "Regioselective imide reduction : An issue in the total synthesis of staurosporine." Tetrahedron Letters 35, no. 49 (December 1994): 9135–38. http://dx.doi.org/10.1016/0040-4039(94)88446-3.

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49

Denislamova, E. S., N. V. Bubnov, and A. N. Maslivets. "ChemInform Abstract: Regioselective Reduction of 1H-Pyrrole-2,3-diones with Thioacetamide." ChemInform 44, no. 36 (August 15, 2013): no. http://dx.doi.org/10.1002/chin.201336104.

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50

IWATA, C., M. FUJIMOTO, M. WATANABE, T. KAWAKAMI, N. MAEDA, T. IMANISHI, and T. TANAKA. "ChemInform Abstract: Regioselective Hydride Reduction of 2-(N-Cyanoimino)thiazolidine Derivatives." ChemInform 23, no. 16 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199216211.

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