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Pure Appl. Chem., 1987, Vol. 59, No. 11, pp. 1509-1520

Synthetic ventures in pseudo-sugar chemistry

T. Suami

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  • Reddy Y. Suman, Kadigachalam P., Basak Ranjan K., John Pal A.P., Vankar Yashwant D.: Total synthesis of (+)-pericosine B and (+)-pericosine C and their enantiomers by using the Baylis–Hillman reaction and ring-closing metathesis as key steps. Tetrahedron Letters 2012, 53, 132. <>
  • 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. <>
  • Gómez Ana M., Uriel Clara, Company Maria D., López J. Cristóbal: Synthetic Strategies Directed Towards 5a-Carbahexopyranoses and Derivatives Based on 6-endo-trig Radical Cyclizations. Eur J Org 2011, 2011, 7116. <>
  • Horasan Kishali Nurhan, Doğan Dilem, Şahin Ertan, Gunel Aslihan, Kara Yunus, Balci Metin: Stereoselective synthesis of deoxycarbaheptopyranose derivatives: 5a-carba-6-deoxy-α-dl-galacto-heptopyranose and 5a-carba-6-deoxy-α-dl-gulo-heptopyranose. Tetrahedron 2011, 67, 1193. <>
  • Salamci Emine: A concise and stereospecific synthesis of some cyclitols containing eight-membered rings: cyclooctane-1,2,3,4-tetraoles. Tetrahedron 2010, 66, 4010. <>
  • Yang Ya-Xi, Li Zheng, Feng Hui-Jin, Chen Guo-Rong, Li Yuan-Chao: Concise synthesis of five-membered ring carbasugars based on key ring-closing metathesis. Tetrahetron Lett 2010, 51, 3848. <>
  • Leermann Timo, Block Oliver, Podeschwa Michael A. L., Pfüller Uwe, Altenbach Hans-Josef: De novo synthesis and lectin binding studies of unsaturated carba-pyranoses. Org Biomol Chem 2010, 8, 3965. <>
  • Cavdar Huseyin, Saracoglu Nurullah: Ring opening of epoxides with NaHSO4: isolation of β-hydroxy sulfate esters and an effective synthesis for trans-diols. Tetrahedron 2009, 65, 985. <>
  • Liu Shi-Ling, Shi Xiao-Xin, Xu Yu-Lan, Xu Wei, Dong Jing: Asymmetric syntheses of (−)-methyl shikimate and (−)-5a-carba-β-d-gulopyranose from d-arabinose via Mukaiyama-type intramolecular aldolization. Tet Asymm 2009, 20, 78. <>
  • Saracoglu Nurullah, Cavdar Huseyin: Synthesis of New β-Hydroxy Nitrate Esters as Potential Glycomimetics or Vasodilators. Eur J Org Chem 2008, 2008, 4615. <>
  • Totokotsopoulos Sotirios M., Koumbis Alexandros E., Gallos John K.: Facile synthesis of 6a-carba-β-d-fructopyranose through an RCM approach. Tetrahedron 2008, 64, 3998. <>
  • 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. <>
  • Usami Yoshihide, Ichikawa Hayato, Arimoto Masao: Synthetic Efforts for Stereo Structure Determination of Cytotoxic Marine Natural Product Pericosines as Metabolites of Periconia sp. from Sea Hare. IJMS 2008, 9, 401. <>
  • González-Bello Concepción, Castedo Luis, Cañada Francisco Javier: Synthesis of Spiro Carba-Sugars by Ring-Closing Metathesis. Eur J Org Chem 2006, 2006, 1002. <>
  • Murugan Andiappan, Yadav Anuj K., Gurjar Mukund K.: Stereoselective syntheses of (+)-proto, (−)-gala quercitols and carba-l-rhamnose from d-(−)-quinic acid. Tetrahetron Lett 2005, 46, 6235. <>
  • Usami Yoshihide, Ueda Yasuko: Synthetic Study toward Antitumour Natural Product Pericosine A. Chem Lett 2005, 34, 1062. <>
  • Usami Yoshihide, Hatsuno Chikage, Yamamoto Hiroe, Tanabe Manabu, Numata Atsushi: Synthesis of the Epimer of Pericosine B from (−)-Quinic Acid. Chem Pharm Bull 2004, 52, 1130. <>
  • López J.Cristóbal, Gómez Ana M., Moreno Eduardo, Danelón Gerardo O., Valverde Serafı́n: Stereodivergent synthesis of 5a-carba-hexopyranoses from carbohydrates via 6-exo-dig radical cyclization: preparation of 5a-carba-β-d-manno-, α-d-allo-, β-l-talo- and α-l-gulopyranose pentaacetates from d-mannose. Tet Asymm 2003, 14, 2961. <>
  • Soengas Raquel G., Estévez Juan C., Estévez Ramón J.: Stereocontrolled Transformation of Nitrohexofuranoses into Cyclopentylamines via 2-Oxabicyclo[2.2.1]heptanes:  Incorporation of Polyhydroxylated Carbocyclic β-Amino Acids into Peptides. Org Lett 2003, 5, 1423. <>
  • Gómez Ana M., Moreno Eduardo, Valverde Serafı́n, López J.Cristóbal: A general stereodivergent strategy for the preparation of carbasugars. Syntheses of 5a-carba-α-d-glucose, α-d-galactose, and β-l-gulose pentaacetates from d-mannose. Tetrahetron Lett 2002, 43, 5559. <>
  • TOYOSHIMA Toshinobu, FUJIHARA Masahiro, TAMAGAKI Seizo: An Implication of Molecular Mechanism for Eliciting Sweetness of Anionic .BETA.-Glycyrrhetinic Acid Derivatives. J Oleo Sci 2002, 51, 313. <>
  • Padwa Albert, Reger Thomas S: Construction of bicyclic tetrahydroisoquinolinones by combination of an IMDAF-ring cleavage reaction of N-allyl-2-furan-2-yl-acetamides. Can J Chem 2000, 78, 749. <>
  • Beusker Patrick H., M. Aben René W., Seerden Jean-Paul G., Smits Jan M. M., Scheeren Hans W.: Exploration of High-Pressure Cycloadducts of Furans and Citraconic Anhydride as Precursors for CD-Ring Fragments of Paclitaxel and Its Analogues. Eur J Org Chem 1998, 1998, 2483. <<2483::AID-EJOC2483>3.0.CO;2-M>
  • Jiang Shende, Singh Gurdial: Chemical synthesis of shikimic acid and its analogues. Tetrahedron 1998, 54, 4697. <>
  • Suami Tetsuo, Hough Leslie, Tsuboi Masamichi, Machinami Tomoya, Watanabe Nobuhiro: Molecular Mechanisms of Sweet Taste. V. Sucralose and Its Derivatives. J Carbohydr Chem 1994, 13, 1079. <>
  • Bach Gabriela, Breiding-Mack Sabine, Grabley Susanne, Hammann Peter, Hütter Klaus, Thiericke Ralf, Uhr Hermann, Wink Joachim, Zeeck Axel: Secondary Metabolites by Chemical Screening, 22. Gabosines, New Carba-sugars FromStreptomyces. Liebigs Ann Chem 1993, 1993, 241. <>
  • Arjona Odón, de Dios Alfonso, Plumet Joaquín: Regio- and stereocontrolled alkylative ring opening of unsymmetrical 8-oxabicyclo[3.2.1]octene systems. Synthesis of highly substituted hydroxycycloheptenyl sulfones. Tetrahetron Lett 1993, 34, 7451. <>
  • Redlich Hartmut, Sudau Wolfgang, Szardenings Anna Katrin, Vollerthun Roland: Radical cyclisation of hept-1-enitols. Carbohydrates Research 1992, 226, 57. <>
  • Lankin David C., Nugent Sean T., Rao Shashidhar N.: NMR spectroscopy and conformational analysis of substituted 1,2:5,6-di-O-isopropylidene-α-d-allofuranose derivatives. Carbohydrates Research 1992, 229, 245. <>
  • Roy Glenn, Zanno Paul R.: A review of sweet taste potentiation brought about by divalent oxygen and sulfur incorporation. Crit Rev Food Sci Technol 1992, 31, 59. <>
  • Suami Tetsuo, Hough Leslie: Molecular Mechanisms of Sweet Taste 1: Sweet and Non-Sweet Tasting Amino Acids. J Carbohydr Chem 1991, 10, 851. <>
  • Koizumi Toru: Sulfinylethenes, Versatile Molecules for the Chiral Synthesis of Bio-Active Compounds. Phosphorus Sulfur Silicon Relat Elem 1991, 58, 111. <>
  • Marschner Christoph, Penn Gerhard, Griengl Herfried: Synthesis of α- and β-D-carbaribofuranose from (+)-norborn-5-en-2-one. Tetrahetron Lett 1990, 31, 2873. <>
  • Arjona Odón, Pradilla Roberto Fernández de la, Martin-Domenech Angel, Plumet Joaquin: Ring-opening Sn2' reactions of 7-oxanorbornenes by organolithium reagents. Regio- and stereospecific synthesis of substituted cyclohexenediols. Tetrahedron 1990, 46, 8187. <>
  • Arjona Odón, de la Pradilla Roberto Fernández, Mallo Araceli, Plumet Joaquin, Viso Alma: Regio- and stereocontrolled synthesis of hydroxycyclohexenyl sulfones from oxanorbornenes. Tetrahetron Lett 1990, 31, 1475. <>
  • Arjona Odón, Fernández de la Pradilla Roberto, García Ernesto, Martin-Domenech Angel, Plumet Joaquín: Regio- and stereospecific synthesis of substituted cyclohexenediols from 7-oxabicyclo[2.2.1]hept-5-en-2-ols and organolithium reagents. Tetrahetron Lett 1989, 30, 6437. <>
  • Tochtermann Werner, Schröder Gunter-Rudolf, Snatzke Günther, Peters Eva-maria, Peters Karl, von Schnering Hans Georg: Tetrahydrofurane und Lactone, I. Synthese und Reaktionen chiraler 2,5-überbrückter Tetrahydrofurane – ein neuer Weg zu optisch aktiven γ-Lactonen und γ-Bislactonen. Chem Ber 1988, 121, 1625. <>