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Pure Appl. Chem., 1997, Vol. 69, No. 1, pp. 97-104

http://dx.doi.org/10.1351/pac199769010097

Synthesis of conduritols and related compounds

Metin Balci

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  • Maldonado Emma, Juárez-Jaimes Verónica: Chemical constituents from Marsdenia callosa. Biochemical Systematics and Ecology 2013, 48, 219. <http://dx.doi.org/10.1016/j.bse.2013.01.005>
  • Aydın Gökay, Savran Tahir, Aktaş Fatih, Baran Arif, Balci Metin: Stereoselective syntheses of racemic quercitols and bromoquercitols starting from cyclohexa-1,4-diene: gala-, epi-, muco-, and neo-quercitol. Org. Biomol. Chem. 2013, 11, 1511. <http://dx.doi.org/10.1039/c3ob26909d>
  • Palframan Matthew J., Kociok-Köhn Gabriele, Lewis Simon E.: Photooxygenation of a Microbial Arene Oxidation Product and Regioselective Kornblum-DeLaMare Rearrangement: Total Synthesis of Zeylenols and Zeylenones. Chemistry A European Journal 2012, 18, 4766. <http://dx.doi.org/10.1002/chem.201104035>
  • Ekmekci Zeynep, Balci Metin: Synthesis of a New 2,3-Diaminoconduritol with Conduritol F Structure. Eur. J. Org. Chem. 2012, 2012, 4988. <http://dx.doi.org/10.1002/ejoc.201200582>
  • Kumar Vikas, Ghosal Partha, Das Pintu, Shaw Arun K.: Highly diastereoselective Morita–Baylis–Hillman chemistry: a remote activation effect in the diastereoface selective synthesis of densely functionalized branched cyclic enones from d-glucose. Tetrahedron: Asymmetry 2012, 23, 449. <http://dx.doi.org/10.1016/j.tetasy.2012.03.009>
  • Yadav Arun A., Sarang Prajakta S., Sau Manishankar, Thirumalairajan Srinath, Trivedi Girish K., Salunkhe Manikrao M.: Synthesis of optically active seven-membered 1,5-anhydrocarbasugars and 1,4,5-tribenzoyloxy-2-ethoxy cycloheptanes via [5+2] cycloaddition. Tetrahedron Letters 2012, 53, 3599. <http://dx.doi.org/10.1016/j.tetlet.2012.05.014>
  • Baran Arif, Bekarlar Merve, Aydin Gökay, Nebioglu Mehmet, Şahin Ertan, Balci Metin: Synthesis of Bishomoinositols and an Entry for Construction of a Substituted 3-Oxabicyclo[3.3.1]nonane Skeleton. J Org Chern 2012, 77, 1244. <http://dx.doi.org/10.1021/jo202494v>
  • Kılbaş Benan, Balci Metin: Recent advances in inositol chemistry: synthesis and applications. Tetrahedron 2011, 67, 2355. <http://dx.doi.org/10.1016/j.tet.2011.01.012>
  • Mahapatra Tridib, Nanda Samik: Asymmetric synthesis of aryl cyclitols based on 1,2,3,4-tetrahydronaphthalene scaffolds. Tet Asymm 2011, 22, 406. <http://dx.doi.org/10.1016/j.tetasy.2011.02.009>
  • Duchek Jan, Adams David R., Hudlicky Tomas: Chemoenzymatic Synthesis of Inositols, Conduritols, and Cyclitol Analogues. Chem Rev 2011, 110609082435081. <http://dx.doi.org/10.1021/cr1004138>
  • BALCI M.: ChemInform Abstract: Synthesis of Conduritols and Related Compounds. ChemInform 2010, 28, no. <http://dx.doi.org/10.1002/chin.199728256>
  • Kurbanoğlu Namudar I., Çelik Murat, Kilic Hamdullah, Alp Cemalettin, Şahin Ertan, Balci Metin: Stereospecific synthesis of a dl-gala-aminoquercitol derivative. Tetrahedron 2010, 66, 3485. <http://dx.doi.org/10.1016/j.tet.2010.03.028>
  • Salamci Emine: A concise and stereospecific synthesis of some cyclitols containing eight-membered rings: cyclooctane-1,2,3,4-tetraoles. Tetrahedron 2010, 66, 4010. <http://dx.doi.org/10.1016/j.tet.2010.04.052>
  • D’Antona Nicola, Nicolosi Giovanni, Morrone Raffaele, Kubáč David, Kaplan Ondřej, Martínková Ludmila: Synthesis of novel cyano-cyclitols and their stereoselective biotransformation catalyzed by Rhodococcus erythropolis A4. Tet Asymm 2010, 21, 695. <http://dx.doi.org/10.1016/j.tetasy.2010.04.022>
  • Bellomo Ana, Camarano Soledad, Rossini Carmen, Gonzalez David: Enantiospecific synthesis and insect feeding activity of sulfur-containing cyclitols. Carbohydrates Research 2009, 344, 44. <http://dx.doi.org/10.1016/j.carres.2008.09.026>
  • Cantekin Seda, Baran Arif, Çalışkan Raşit, Balci Metin: Synthesis of bromo-conduritol-B and bromo-conduritol-C as glycosidase inhibitors. Carbohydrates Research 2009, 344, 426. <http://dx.doi.org/10.1016/j.carres.2008.12.005>
  • Şahin Ertan, Baran Arif, Balcı Metin: rac-(2R*,3S*,5S*,6R*,7S*,8S*)-7,8-Dichlorobicyclo[2.2.2]octane-2,3,5,6-tetrayl tetraacetate. Acta Crystallogr E Struct Rep Online 2009, 65, o526. <http://dx.doi.org/10.1107/S160053680900484X>
  • Sengül Mehmet Emin, Menzek Abdullah, Sahin Ertan, Arik Mustafa, Saracoglu Nurullah: Synthesis of cyclopropane-annulated conduritol derivatives: norcaran-2,3,4,5-tetraoles. Tetrahedron 2008, 64, 7289. <http://dx.doi.org/10.1016/j.tet.2008.05.066>
  • Doddi Venkata Ramana, Kumar Amit, Vankar Yashwant D.: Stereoselective synthesis of muco-quercitol, (+)-gala-quercitol and 5-amino-5-deoxy-d-vibo-quercitol from d-mannitol. Tetrahedron 2008, 64, 9117. <http://dx.doi.org/10.1016/j.tet.2008.06.107>
  • Lang Martin, Ziegler Thomas: Synthesis of Both Enantiomers of Conduritol C Tetraacetate and ofmeso-Conduritol D Tetraacetate by Oxidation of Benzoquinone Bis(ethylene acetal). Eur J Org Chem 2007, 2007, 768. <http://dx.doi.org/10.1002/ejoc.200600764>
  • Cantekin Seda, Çalışkan Raşit, Şahin Ertan, Balci Metin: Synthesis of Phenyl-Substituted Conduritol B and Its Mechanism of Formation. HCA 2007, 90, 2227. <http://dx.doi.org/10.1002/hlca.200790231>
  • Łysek Robert, Vogel Pierre: Synthesis of amino- and diaminoconduritols and their applications. Tetrahedron 2006, 62, 2733. <http://dx.doi.org/10.1016/j.tet.2005.11.046>
  • Yardımcı Şengül Dilem, Kaya Nihal, Balci Metin: Regioselectivity in the ene-reaction of singlet oxygen with cyclic alkenes: photooxygenation of methyl-substituted 1,4-cyclohexadiene derivatives. Tetrahedron 2006, 62, 10633. <http://dx.doi.org/10.1016/j.tet.2006.07.103>
  • Kelebekli Latif, Kara Yunus, Balci Metin: Stereospecific synthesis of a new class of compounds: bis-homoconduritol-A, -D, and -F. Carbohydrates Research 2005, 340, 1940. <http://dx.doi.org/10.1016/j.carres.2005.05.021>
  • Gómez Ana M., Moreno Eduardo, Uriel Clara, Jarosz Slawomir, Valverde Serafín, López J. Cristóbal: Novel strategies for the preparation of aminocarbasugar analogues: syntheses of N-substituted aminocyclitols from d-mannose. Tet Asymm 2005, 16, 2401. <http://dx.doi.org/10.1016/j.tetasy.2005.05.033>
  • Güney Murat, Ceylan Zeynep Çelik, Daştan Arif, Balci Metin: Substituent effects of the cycloaddition reaction of 7-substituted 5H-benzocycloheptenes with singlet oxygen and the chemistry of the benzocycloheptene endoperoxides. Can J Chem 2005, 83, 227. <http://dx.doi.org/10.1139/v05-046>
  • Orsini Fulvia, Sello Guido, Bernasconi Silvana, Fallacara Gianfranco: Chemoenzymatic synthesis of conduritol analogues. Tetrahetron Lett 2004, 45, 9253. <http://dx.doi.org/10.1016/j.tetlet.2004.10.072>
  • Gültekin M.Serdar, Salamci Emine, Balci Metin: A novel and short synthesis of (1,4/2)-cyclohex-5-ene-triol and its conversion to (±)-proto-quercitol. Carbohydrates Research 2003, 338, 1615. <http://dx.doi.org/10.1016/S0008-6215(03)00256-8>
  • Kara Yunus, Balci Metin: A new and stereospecific synthesis of an inositol analogue: bis-homoinositol. Tetrahedron 2003, 59, 2063. <http://dx.doi.org/10.1016/S0040-4020(03)00209-6>
  • Heo Jung-Nyoung, Holson Edward B., Roush William R.: Common-Intermediate Strategy for Synthesis of Conduritols and Inositols via β-Hydroxy Cyclohexenylsilanes. Org Lett 2003, 5, 1697. <http://dx.doi.org/10.1021/ol034349d>
  • Crowley Patrick J., Fawcett John, Kariuki Benson M., Moralee Andrew C., Percy Jonathan M., Salafia Vittoria: Basic and Reductive Sulfone-Directed Ring-Opening Reactions of Difluorinated Oxa[2.2.1]bicycloheptanes. Org Lett 2002, 4, 4125. <http://dx.doi.org/10.1021/ol0268743>
  • Dastan Arif, Saracoglu Nurullah, Balci Metin: A New Method for the Synthesis of Stipitatic Acid Isomers: Photooxygenation of Ethyl 6H-Cyclohepta[d][1,3]dioxole-6-carboxylate. Eur J Org Chem 2001, 2001, 3519. <http://dx.doi.org/10.1002/1099-0690(200109)2001:18<3519::AID-EJOC3519>3.0.CO;2-2>
  • Trost Barry M., Dudash, Jr. Joseph, Hembre Erik J.: Asymmetric Induction of Conduritols via AAA Reactions: Synthesis of the Aminocyclohexitol of Hygromycin A. Chem Eur J 2001, 7, 1619. <http://dx.doi.org/10.1002/1521-3765(20010417)7:8<1619::AID-CHEM16190>3.0.CO;2-4>
  • Mehta Goverdhan, Ramesh Senaiar S: Polycyclitols: synthesis of novel carbasugar and conduritol analogues as potential glycosidase inhibitors. Tetrahetron Lett 2001, 42, 1987. <http://dx.doi.org/10.1016/S0040-4039(01)00050-8>
  • Kwon Yong-Uk, Chung Sung-Kee: Facile Synthetic Routes to All Possible Enantiomeric Pairs of Conduritol Stereoisomers via Efficient Enzymatic Resolution of Conduritol B and C Derivatives. Org Lett 2001, 3, 3013. <http://dx.doi.org/10.1021/ol0164233>
  • Dalko Peter I., Sinaÿ Pierre: Neue Fortschritte bei der Umwandlung von Kohlenhydratfuranosiden und -pyranosiden zu Carbocyclen. Angew Chem 1999, 111, 819. <http://dx.doi.org/10.1002/(SICI)1521-3757(19990315)111:6<819::AID-ANGE819>3.0.CO;2-S>
  • Cerè Vanda, Peri Francesca, Pollicino Salvatore: Synthesis of Enantiopure Polyhydroxylated Carbo and Sulfurated Cycles with Potential or Proved Biological Activity, Starting from D-Mannitol. Phosphorus Sulfur Silicon Relat Elem 1999, 153, 305. <http://dx.doi.org/10.1080/10426509908546443>
  • Arjona Odón, Iradier Fátima, Mañas Rosario M., Plumet Joaquín: Synthesis of a protected derivative of (±)-1-(hydroxymethyl)conduritol C from 2-(hydroxymethyl)furan. Tetrahetron Lett 1998, 39, 8335. <http://dx.doi.org/10.1016/S0040-4039(98)01936-4>
  • IKEDA Hajime, SUGAI Takeshi, HOSOMI Hiroyuki, OHBA Shigeru, OHTA Hiromichi: Syntheses of Highly Oxygen-functionalized Derivatives of Dihydrodihydroxyphthalic Acid in Enantiomerically Enriched Forms. Biosci Biotechnol Biochem 1998, 62, 396. <http://dx.doi.org/10.1271/bbb.62.396>
  • Lallemand Marie-Christine, Desjardins Michel, Freeman Stanley, Hudlicky Tomas: Synthesis of conduritol, conduramine, and validoxylamine analogs from tetrahydronaphthalene-cis-diol. Tetrahetron Lett 1997, 38, 7693. <http://dx.doi.org/10.1016/S0040-4039(97)10008-9>