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Journal articles on the topic 'Asymmetric carbocycle synthesis'

Author: Grafiati

Published: 4 June 2021

Last updated: 8 February 2022

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1

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

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2

Schwarz, Jacob B., and A. I. Meyers. "Tandem α-Cyano Enamine/Enolate Alkylations on Bicyclic Lactams: Asymmetric Carbocycle and Heterocycle Synthesis." Journal of Organic Chemistry 63, no. 5 (March 1998): 1619–29. http://dx.doi.org/10.1021/jo971920b.

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3

Marcantonio, Enrico, Claudio Curti, Lucia Battistini, Andrea Sartori, Luana Cardinale, Giorgio Pelosi, and Franca Zanardi. "Direct, Asymmetric Synthesis of Carbocycle‐Fused Uracils via [4+2] Cycloadditions: a Noncovalent Organocatalysis Approach." Advanced Synthesis & Catalysis 363, no. 10 (March 31, 2021): 2625–33. http://dx.doi.org/10.1002/adsc.202100082.

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4

Bhuniya, Rajib, Tridib Mahapatra, and Samik Nanda. "Klebsiellapneumoniae (NBRC 3319) Mediated Asymmetric Reduction of α-Substituted β-Oxo Esters and Its Application to the Enantioiselective Synthesis of Small-Ring Carbocycle Derivatives." European Journal of Organic Chemistry 2012, no. 8 (January 30, 2012): 1597–602. http://dx.doi.org/10.1002/ejoc.201101695.

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5

Bhuniya, Rajib, Tridib Mahapatra, and Samik Nanda. "ChemInform Abstract: Klebsiella pneumoniae (NBRC 3319) Mediated Asymmetric Reduction of α-Substituted β-Oxo Esters and Its Application to the Enantioselective Synthesis of Small-Ring Carbocycle Derivatives." ChemInform 43, no. 30 (July 3, 2012): no. http://dx.doi.org/10.1002/chin.201230035.

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6

Ren, Qiao, Muyao Li, Lujiang Yuan, and Jian Wang. "Recent advances in N-heterocyclic carbene catalyzed achiral synthesis." Organic & Biomolecular Chemistry 15, no. 22 (2017): 4731–49. http://dx.doi.org/10.1039/c7ob00568g.

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This review reveals the recent developments in NHC-promoted non-asymmetric umpolung transformations resulting in the expeditious construction of versatile achiral natural heterocycles, carbocycles and acylated products.

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7

Meier, Chris, Simon Weising, and Ilaria Torquati. "Stereoselective Synthesis of 1′,2′-cis-Disubstituted Carbocyclic ribo-Nucleoside Analogues." Synthesis 50, no. 06 (December 20, 2017): 1264–74. http://dx.doi.org/10.1055/s-0036-1591732.

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Herein we disclose an efficient strategy for the convergent synthesis of 1′,2′-cis-disubstituted carbocyclic ribo-nucleoside analogues. Starting from an enantiomerically pure cyclopentenol precursor, the key step for the preparation of the highly functionalized carbocyclic building block is an asymmetric dihydroxylation. Employing different variants of the Mitsunobu protocol, the condensation with all-natural nucleobases or their precursors affords a series of ribo-configured carbocyclic 1′,2′-cis-disubstituted nucleoside analogues.

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8

Schneider, Lisa M., Volker M. Schmiedel, Tommaso Pecchioli, Dieter Lentz, Christian Merten, and Mathias Christmann. "Asymmetric Synthesis of Carbocyclic Propellanes." Organic Letters 19, no. 9 (April 26, 2017): 2310–13. http://dx.doi.org/10.1021/acs.orglett.7b00836.

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9

Hanessian, Stephen, Andrew M. Griffin, and Louis-David Cantin. "Asymmetric synthesis of functionalized carbocycles and heterocycles." Chirality 12, no. 5-6 (2000): 342–45. http://dx.doi.org/10.1002/(sici)1520-636x(2000)12:5/6<342::aid-chir7>3.0.co;2-y.

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10

Zhao, Y. F., M. G. Lee, T. F. Yang, B. K. Chun, J. F. Du, R. F. Schinazi, and C. K. Chu. "Asymmetric Synthesis of Cyclopropyl Carbocyclic Nucleosides." Nucleosides, Nucleotides and Nucleic Acids 14, no. 3 (May 1, 1995): 303–5. http://dx.doi.org/10.1080/15257779508012367.

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11

Wang, Peiyuan, Luigi A. Agrofoglio, M. Gary Newton, and Chung K. Chu. "Asymmetric synthesis of L-cyclopentyl carbocyclic nucleosides." Tetrahedron Letters 38, no. 24 (June 1997): 4207–10. http://dx.doi.org/10.1016/s0040-4039(97)00898-8.

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12

Sreedharan, Dinesh T., and Derrick L. J. Clive. "Asymmetric synthesis of carbocycles: use of intramolecular conjugate displacement." Organic & Biomolecular Chemistry 11, no. 19 (2013): 3128. http://dx.doi.org/10.1039/c3ob40115d.

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13

ZHAO, Y. F., M. G. LEE, T. F. YANG, B. K. CHUN, J. F. DU, R. F. SCHINAZI, and C. K. CHU. "ChemInform Abstract: Asymmetric Synthesis of Cyclopropyl Carbocyclic Nucleosides." ChemInform 26, no. 39 (August 17, 2010): no. http://dx.doi.org/10.1002/chin.199539249.

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14

Aggarwal, Varinder K., and Nuno Monteiro. "Asymmetric total synthesis of (+)-carbocyclic uracil polyoxin C." Journal of the Chemical Society, Perkin Transactions 1, no. 17 (1997): 2531–38. http://dx.doi.org/10.1039/a702323e.

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15

Inanaga, Kazato, Marco Wollenburg, Shoshana Bachman, Nicholas J. Hafeman, and Brian M. Stoltz. "Catalytic enantioselective synthesis of carbocyclic and heterocyclic spiranes via a decarboxylative aldol cyclization." Chemical Science 11, no. 28 (2020): 7390–95. http://dx.doi.org/10.1039/d0sc02366c.

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16

Kitamura, Masato, Kengo Miyata, Tomoaki Seki, Namdev Vatmurge, and Shinji Tanaka. "CpRu-catalyzed asymmetric dehydrative allylation." Pure and Applied Chemistry 85, no. 6 (April 15, 2013): 1121–32. http://dx.doi.org/10.1351/pac-con-12-10-02.

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Asymmetric Tsuji–Trost allylation is one of the key chiral technologies for construction of pharmaceutically important compounds because of the high utility of alkenyl-substituted products. Particularly, the dehydrative system using allylic alcohols and protic nucleophiles has started to attract the attention of organic synthetic chemists from the viewpoints of atom and step economy, environmental benignity, and operational simplicity. In this paper, two types of new chiral CpRu catalysts, which have been developed on the basis of redox-mediated donor–acceptor bifunctional catalyst (RDACat) concept, are presented. Complementary use of the chiral catalysts has realized the syntheses of a wide rage of carbocyclic compounds, saturated N- or O-heterocyclic compounds with high reactivity, regioselectivity, enantioselectivity, productivity, and generality.

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17

Gao, Yuan, Xiaonan Wang, Zhonglin Wei, Jungang Cao, Dapeng Liang, Yingjie Lin, and Haifeng Duan. "Asymmetric synthesis of spirooxindole–pyranoindole products via Friedel–Crafts alkylation/cyclization of the indole carbocyclic ring." New Journal of Chemistry 44, no. 23 (2020): 9788–92. http://dx.doi.org/10.1039/d0nj00074d.

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18

WANG, P., L. A. AGROFOLIO, M. G. NEWTON, and C. K. CHU. "ChemInform Abstract: Asymmetric Synthesis of L-Cyclopentyl Carbocyclic Nucleosides." ChemInform 28, no. 37 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199737248.

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19

Tanimori, Shinji, Masakazu Tsubota, Mingqi He, and Mitsuru Nakayama. "A Concise Enantioselective Pathway to Carbocyclic Nucleoside: Asymmetric Synthesis of Carbocyclic Moiety of Carbovir." Synthetic Communications 27, no. 14 (July 1997): 2371–78. http://dx.doi.org/10.1080/00397919708004098.

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20

Sreedharan, Dinesh, and Derrick L. J. Clive. "ChemInform Abstract: Asymmetric Synthesis of Carbocycles: Use of Intramolecular Conjugate Displacement." ChemInform 44, no. 36 (August 15, 2013): no. http://dx.doi.org/10.1002/chin.201336030.

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21

Ohfune, Yasufumi, Kousuke Nanba, Ichinori Takada, Toshiyuki Kan, Manabu Horikawa, and Terumi Nakajima. "Asymmetric syntheses of 5- and 6-membered carbocyclic serine analogs via an intramolecular Strecker synthesis." Chirality 9, no. 5-6 (1997): 459–62. http://dx.doi.org/10.1002/(sici)1520-636x(1997)9:5/6<459::aid-chir11>3.0.co;2-n.

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22

Wang, Hai-Xia, Wen-Peng Li, Chao Xia, Ming-Sheng Xie, Gui-Rong Qu, and Hai-Ming Guo. "Enantioselective synthesis of chiral carbocyclic pyrimidine nucleosides via asymmetric cyclopropanation." Tetrahedron Letters 60, no. 43 (October 2019): 151183. http://dx.doi.org/10.1016/j.tetlet.2019.151183.

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23

Zhao, Yufen, Tefang Yang, Migyoung Lee, Doowon Lee, M. Gary Newton, and Chung K. Chu. "Asymmetric Synthesis of (1'S,2'R)-Cyclopropyl Carbocyclic Nucleosides." Journal of Organic Chemistry 60, no. 16 (August 1995): 5236–42. http://dx.doi.org/10.1021/jo00121a047.

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24

AGGARWAL, V. K., and N. MONTEIRO. "ChemInform Abstract: Asymmetric Total Synthesis of (+)-Carbocyclic Uracil Polyoxin C." ChemInform 28, no. 51 (August 2, 2010): no. http://dx.doi.org/10.1002/chin.199751251.

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25

Shi, Junxing, and Raymond F. Schinazi. "ASYMMETRIC SYNTHESIS OF CARBOCYCLIC PYRIMIDINE NUCLEOSIDES VIA π-ALLYLPALLADIUM COMPLEX." Nucleosides, Nucleotides and Nucleic Acids 20, no. 4-7 (March 31, 2001): 1367–70. http://dx.doi.org/10.1081/ncn-100002557.

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26

TANIMORI, S., M. TSUBOTA, M. HE, and M. NAKAYAMA. "ChemInform Abstract: A Concise Enantioselective Pathway to Carbocyclic Nucleoside: Asymmetric Synthesis of Carbocyclic Moiety of Carbovir." ChemInform 28, no. 38 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199738275.

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27

Vogt, Paul F., Jan-Gerd Hansel, and Marvin J. Miller. "Asymmetric synthesis of an important precursor to 5′-nor carbocyclic nucleosides." Tetrahedron Letters 38, no. 16 (April 1997): 2803–4. http://dx.doi.org/10.1016/s0040-4039(97)00511-x.

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28

Narasaka, Koichi, Kazuhiro Hayashi, and Yujiro Hayashi. "Asymmetric synthesis of methylenecyclobutanes and their transformation to medium-sized carbocyclic compounds." Tetrahedron 50, no. 15 (April 1994): 4529–42. http://dx.doi.org/10.1016/s0040-4020(01)89384-4.

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29

Hanessian, Stephen, Dilip K. Maji, Subramaniyan Govindan, Riccardo Matera, and Marina Tintelnot-Blomley. "Substrate-Controlled and Organocatalytic Asymmetric Synthesis of Carbocyclic Amino Acid Dipeptide Mimetics." Journal of Organic Chemistry 75, no. 9 (May 7, 2010): 2861–76. http://dx.doi.org/10.1021/jo100017t.

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30

ZHAO, Y., T. YANG, M. LEE, D. LEE, M. G. NEWTON, and C. K. CHU. "ChemInform Abstract: Asymmetric Synthesis of (1′S,2′R)-Cyclopropyl Carbocyclic Nucleosides." ChemInform 26, no. 50 (August 16, 2010): no. http://dx.doi.org/10.1002/chin.199550209.

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31

Shi, Junxing, and Raymond F. Schinazi. "ChemInform Abstract: Asymmetric Synthesis of Carbocyclic Pyrimidine Nucleosides via π-Allylpalladium Complex." ChemInform 32, no. 49 (May 23, 2010): no. http://dx.doi.org/10.1002/chin.200149235.

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32

Crimmins, Michael T., Bryan W. King, William J. Zuercher, and Allison L. Choy. "An Efficient, General Asymmetric Synthesis of Carbocyclic Nucleosides: Application of an Asymmetric Aldol/Ring-Closing Metathesis Strategy." Journal of Organic Chemistry 65, no. 25 (December 2000): 8499–509. http://dx.doi.org/10.1021/jo005535p.

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33

Pai Fondekar, Kamalesh P., Franz-J. Volk, S. M. Khaliq-uz-Zaman, Philippe Bisel, and August W. Frahm. "Carbocyclic α,β-diamino acids: asymmetric Strecker synthesis of stereomeric 1,2-diaminocyclohexanecarboxylic acids." Tetrahedron: Asymmetry 13, no. 20 (October 2002): 2241–49. http://dx.doi.org/10.1016/s0957-4166(02)00610-9.

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34

VOGT, P. F., J. G. HANSEL, and M. J. MILLER. "ChemInform Abstract: Asymmetric Synthesis of an Important Precursor to 5′-Nor-carbocyclic Nucleosides." ChemInform 28, no. 31 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199731199.

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35

Crimmins, Michael T., and Bryan W. King. "An Efficient Asymmetric Approach to Carbocyclic Nucleosides: Asymmetric Synthesis of 1592U89, a Potent Inhibitor of HIV Reverse Transcriptase." Journal of Organic Chemistry 61, no. 13 (January 1996): 4192–93. http://dx.doi.org/10.1021/jo960708p.

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36

Kumar, Rajan, Rohan Kalyan Rej, Joydev Halder, Haridas Mandal, and Samik Nanda. "Enantiopure hydroxymethylated cycloalkenols as privileged small molecular multifunctional scaffolds for the asymmetric synthesis of carbocycles." Tetrahedron: Asymmetry 27, no. 11-12 (July 2016): 498–512. http://dx.doi.org/10.1016/j.tetasy.2016.05.003.

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37

Kerr, Daniel J., Jonathan M. White, and Bernard L. Flynn. "A Reductive-Coupling plus Nazarov Cyclization Sequence in the Asymmetric Synthesis of Five-Membered Carbocycles." Journal of Organic Chemistry 75, no. 21 (November 5, 2010): 7073–84. http://dx.doi.org/10.1021/jo100736p.

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38

Marco-Contelles, José, and Manuel Bernabé. "Asymmetric synthesis of cyclopentylamine derivatives, intermediates for carbocyclic nucleoside synthesis. Carbocyclization of 2-amino-5-hexenyl radicals." Tetrahedron Letters 35, no. 34 (August 1994): 6361–64. http://dx.doi.org/10.1016/s0040-4039(00)73433-2.

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39

Pai Fondekar, Kamalesh, Franz-J. Volk, and August W. Frahm. "Carbocyclic α-amino acids: asymmetric synthesis of all four 1-amino-2-hydroxycyclohexanecarboxylic acids." Tetrahedron: Asymmetry 10, no. 4 (February 1999): 727–35. http://dx.doi.org/10.1016/s0957-4166(99)00045-2.

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40

Jeong, Lak Shin, Jeong A. Lee, Hyung Ryong Moon, Hea Ok Kim, Kang Man Lee, Hyun Joo Lee, and Moon Woo Chun. "Asymmetric Synthesis of Novel Apio Carbocyclic Nucleoside Analogues as Potential Antiviral and Antitumor Agent." Nucleosides, Nucleotides and Nucleic Acids 26, no. 6-7 (November 26, 2007): 721–24. http://dx.doi.org/10.1080/15257770701493237.

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41

NARASAKA, K., K. HAYASHI, and Y. HAYASHI. "ChemInform Abstract: Asymmetric Synthesis of Methylenecyclobutanes and Their Transformation to Medium-Sized Carbocyclic Compounds." ChemInform 25, no. 32 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199432035.

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42

Tanaka, Masakazu, Yoshihiko Norimine, Toshiaki Fujita, Hiroshi Suemune, and Kiyoshi Sakai. "Chemoenzymatic Synthesis of Antiviral Carbocyclic Nucleosides: Asymmetric Hydrolysis ofmeso-3,5-Bis(acetoxymethyl)cyclopentenes UsingRhizopusdelemarLipase." Journal of Organic Chemistry 61, no. 20 (January 1996): 6952–57. http://dx.doi.org/10.1021/jo9608230.

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43

Marcé, Patricia, Yolanda Díaz, M. Isabel Matheu, and Sergio Castillón. "Synthesis ofd- andl-Carbocyclic Nucleosides via Rhodium-Catalyzed Asymmetric Hydroacylation as the Key Step." Organic Letters 10, no. 21 (November 6, 2008): 4735–38. http://dx.doi.org/10.1021/ol801791g.

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44

Crimmins, Michael T., Bryan W. King, William J. Zuercher, and Allison L. Choy. "ChemInform Abstract: An Efficient, General Asymmetric Synthesis of Carbocyclic Nucleosides: Application of an Asymmetric Aldol/Ring-Closing Metathesis Strategy." ChemInform 32, no. 17 (April 24, 2001): no. http://dx.doi.org/10.1002/chin.200117211.

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45

Trost, Barry M., Steven M. Silverman, and James P. Stambuli. "Development of an Asymmetric Trimethylenemethane Cycloaddition Reaction: Application in the Enantioselective Synthesis of Highly Substituted Carbocycles." Journal of the American Chemical Society 133, no. 48 (December 7, 2011): 19483–97. http://dx.doi.org/10.1021/ja207550t.

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46

Maruoka, Keiji, Susumu Saito, Takashi Ooi, and Hisashi Yamamoto. "A New Stereoselective Approach to Oxygenated Carbocycles: Asymmetric Synthesis of the Cyclohexyl Fragment of FK-506." Synlett 1991, no. 08 (1991): 579–80. http://dx.doi.org/10.1055/s-1991-21983.

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47

Adly, Frady G., and Ashraf Ghanem. "Chiral Dirhodium(II) Carboxylates and Carboxamidates as Effective Chemzymes in Asymmetric Synthesis of Three-Membered Carbocycles." Chirality 26, no. 11 (July 15, 2014): 692–711. http://dx.doi.org/10.1002/chir.22347.

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48

Wu, Jie, Yi Pu, and James S. Panek. "Divergent Synthesis of Functionalized Carbocycles through Organosilane-Directed Asymmetric Alkyne–Alkene Reductive Coupling and Annulation Sequence." Journal of the American Chemical Society 134, no. 44 (October 23, 2012): 18440–46. http://dx.doi.org/10.1021/ja3083945.

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49

Littlechild, Jennifer A. "Thermophilic archaeal enzymes and applications in biocatalysis." Biochemical Society Transactions 39, no. 1 (January 19, 2011): 155–58. http://dx.doi.org/10.1042/bst0390155.

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Thermophilic enzymes have advantages for their use in commercial applications and particularly for the production of chiral compounds to produce optically pure pharmaceuticals. They can be used as biocatalysts in the application of ‘green chemistry’. The thermophilic archaea contain enzymes that have already been used in commercial applications such as the L-aminoacylase from Thermococcus litoralis for the resolution of amino acids and amino acid analogues. This enzyme differs from bacterial L-aminoacylases and has similarities to carboxypeptidases from other archaeal species. An amidase/γ-lactamase from Sulfolobus solfataricus has been used for the production of optically pure γ-lactam, the building block for antiviral carbocyclic nucleotides. This enzyme has similarities to the bacterial signature amidase family. An alcohol dehydrogenase from Aeropyrum pernix has been used for the production of optically pure alcohols and is related to the zinc-containing eukaryotic alcohol dehydrogenases. A transaminase and a dehalogenase from Sulfolobus species have also been studied. The archaeal transaminase is found in a pathway for serine synthesis which is found only in eukaryotes and not in bacteria. It can be used for the asymmetric synthesis of homochiral amines of high enantioselective purity. The L-2-haloacid dehalogenase has applications both in biocatalysis and in bioremediation. All of these enzymes have increased thermostability over their mesophilic counterparts.

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50

Wang, Peiyuan, Raymond F. Schinazi, and Chung K. Chu. "Asymmetric synthesis and anti-HIV activity of L-carbocyclic 2′,3′-didehydro-2′,3′-dideoxyadenosine." Bioorganic & Medicinal Chemistry Letters 8, no. 13 (July 1998): 1585–88. http://dx.doi.org/10.1016/s0960-894x(98)00278-9.

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