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Pure Appl. Chem., 1987, Vol. 59, No. 3, pp. 415-424

http://dx.doi.org/10.1351/pac198759030415

De novo synthesis of carbohydrates and related natural products

R. R. Schmidt

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  • Leonori Daniele, Seeberger Peter H.: De Novo Synthesis of the Bacterial 2-Amino-2,6-Dideoxy Sugar Building Blocks d-Fucosamine, d-Bacillosamine, and d-Xylo-6-deoxy-4-ketohexosamine. Org. Lett. 2012, 14, 4954. <http://dx.doi.org/10.1021/ol3023227>
  • Giguère Denis, Martel Julien, Shiao Tze Chieh, Roy René: Enantioselective de Novo Synthesis of 4-Deoxy-d-hexopyranoses via Hetero-Diels–Alder Cycloadditions: Total Synthesis of Ezoaminuroic Acid and Neosidomycin. J Org Chern 2011, 76, 9687. <http://dx.doi.org/10.1021/jo201673w>
  • Vogel Pierre: Synthesis of Rare Carbohydrates and Biomolecules from Furan. Bull Soc Chim Belges 2010, 99, 395. <http://dx.doi.org/10.1002/bscb.19900990606>
  • Gruppenselektive Reaktionen. Nachr Chem Tech Lab 2010, 41, 314. <http://dx.doi.org/10.1002/nadc.19930410310>
  • Bindschädler Pascal, Adibekian Alexander, Grünstein Dan, Seeberger Peter H.: De novo synthesis of differentially protected l-iduronic acid glycosylating agents. Carbohydrates Research 2010, 345, 948. <http://dx.doi.org/10.1016/j.carres.2010.02.004>
  • Dziedzic Magdalena, Furman Bartłomiej: An efficient approach to the stereoselective synthesis of 2,6-disubstituted dihydropyrans via stannyl-Prins cyclization. Tetrahetron Lett 2008, 49, 678. <http://dx.doi.org/10.1016/j.tetlet.2007.11.128>
  • Adibekian Alexander, Bindschädler Pascal, Timmer Mattie S. M., Noti Christian, Schützenmeister Nina, Seeberger Peter H.: De Novo Synthesis of Uronic Acid Building Blocks for Assembly of Heparin Oligosaccharides. Chem Eur J 2007, 13, 4510. <http://dx.doi.org/10.1002/chem.200700141>
  • Timmer Mattie S. M., Adibekian Alexander, Seeberger Peter H.: De-novo-Synthese von vollständig funktionalisierten Uronsäure-Monosacchariden. Angew Chem 2005, 117, 7777. <http://dx.doi.org/10.1002/ange.200502742>
  • Timmer Mattie S. M., Adibekian Alexander, Seeberger Peter H.: Short De Novo Synthesis of Fully Functionalized Uronic Acid Monosaccharides. Angew Chem Int Ed 2005, 44, 7605. <http://dx.doi.org/10.1002/anie.200502742>
  • Tietze Lutz F., Schneider Christoph, Grote Andrea: Stereodivergent Hetero-Diels-Alder Reactions of Chiral 1-Oxa-1,3-butadienes through a Conformational Switch Induced by Lewis Acids. Chem Eur J 1996, 2, 139. <http://dx.doi.org/10.1002/chem.19960020205>
  • Zhuo Jin-Cong, Wyler Hugo, Schenk Kurt: Hetero-Diels-Alder Additions of α,β-Unsaturated-Acyl Cyanides. Part 3. Syntheses of 3-bromo-2-ethoxy-3,4-dihydro-2H-pyran-6-carbonitriles, and about their transformation to 2-ethoxy-2H-pyrans. HCA 1995, 78, 151. <http://dx.doi.org/10.1002/hlca.19950780115>
  • Tietze Lutz F., Schulz Gerhard: Molecular switches: Calculations on the stereodivergent hetero Diels-Alder reaction of chiral 1-oxa-1,3-butadienes with different lewis acids. Liebigs Ann /Recueil 1995, 1995, 1921. <http://dx.doi.org/10.1002/jlac.1995199511271>
  • Eisele Thomas, Ishida Hideharu, Hummel Gerd, Schmidt Richard R.: Synthesis of carbon-bridgedN-acetyl-c-lactosamine and derivatives. Liebigs Ann /Recueil 1995, 1995, 2113. <http://dx.doi.org/10.1002/jlac.1995199512297>
  • Tietze Lutz F., Schneider Christoph, Montenbruck Andrea: Asymmetrisch 1,6-induzierte Hetero-Diels-Alder-Reaktion chiraler Oxabutadiene zur De-novo-Synthese enantiomerenreiner Kohlenhydrate: Umkehr der Seitendifferenzierung durch Variation des Lewis-Säure-Initiators. Angew Chem 1994, 106, 1031. <http://dx.doi.org/10.1002/ange.19941060915>
  • Jung Michael E., Gardiner John M.: Asymmetric synthesis of carbohydrates: Synthesis of 2-deoxy-D- and 2-deoxy-L-xylofuranosides from a simple achiral precursor. Tetrahetron Lett 1994, 35, 6755. <http://dx.doi.org/10.1016/S0040-4039(00)73487-3>
  • Preuss Rainer, Jung Karl-Heinz, Schmidt Richard R.: Spiroketal Synthesis. — A Case of Intramolecular Glycoside Bond Formation. Liebigs Ann Chem 1992, 1992, 377. <http://dx.doi.org/10.1002/jlac.199219920166>
  • Maier Thomas, Schmidt Richard R.: Synthesis of methyl 4-acetamido-2,4-dideoxy-d-glycero-d-galacto-octopyranoside, a decarboxyneuraminic acid analogue. Carbohydrates Research 1992, 216, 483. <http://dx.doi.org/10.1016/0008-6215(92)84183-S>
  • Neff Denis-Pierre, Chen Yuanwei, Vogel Pierre: A New Total Synthesis ofD-threo-L-talo-Octose. HCA 1991, 74, 508. <http://dx.doi.org/10.1002/hlca.19910740307>
  • Reißig Hans-Ulrich, Hippeli Claudia, Arnold Thomas: On the mechanism of diels-alder reactions of nitroso alkenes:exo/endo selectivity, stereospecificity,E/Z selectivity, and relative reactivity of various olefins. Chem Ber 1990, 123, 2403. <http://dx.doi.org/10.1002/cber.19901231224>
  • Haag-Zeino Brigitte, Schmidt Richard R.: De novo synthesis of carbohydrates and related natural products, 34. Synthesis ofN-acetyl-β-D-neuraminic acid derivatives via inverse-type hetero-Diels-Alder reaction. Liebigs Ann Chem 1990, 1990, 1197. <http://dx.doi.org/10.1002/jlac.1990199001217>
  • Maier Sibylle, Preuss Rainer, Schmidt Richard R.: Functionally substituted vinyl carbanions, 40. Synthesis of the basic structure of ezomycin A. Liebigs Ann Chem 1990, 1990, 483. <http://dx.doi.org/10.1002/jlac.199019900191>
  • Denmark Scott E., Senanayake C.B.W., Ginny-Dai Ho: Tandem [4+2]/[3+2]-cycloadditions. 2. Asymmetric induction with a chiral vinyl ether. Tetrahedron 1990, 46, 4857. <http://dx.doi.org/10.1016/S0040-4020(01)85599-X>
  • De Gaudenzi Luigi, Apparao Satyam, Schmidt Richard R.: Synthesis of 2-deoxy-L- and -D-galacto-heptose via inverse type hetero-diels-alder reaction. Tetrahedron 1990, 46, 277. <http://dx.doi.org/10.1016/S0040-4020(01)97598-2>
  • Coleman Robert S., Grant Eugene B.: Cycloaddition reactions of acyl ketenes with enol ethers: A general synthesis of 2-alkoxy-2,3-dihydro-4h-pyran-4-ones. Tetrahetron Lett 1990, 31, 3677. <http://dx.doi.org/10.1016/S0040-4039(00)97442-2>
  • Auberson Yves, Vogel Pierre: Total Synthesis ofL-Allose,L-Talose, and derivatives. HCA 1989, 72, 278. <http://dx.doi.org/10.1002/hlca.19890720212>
  • Preuss Rainer, Schmidt Richard R.: Funktionell substituierte Vinylcarbanionen, 38.C-Glucoside durch direkte 1-C-Lithiierung von 2-Phenylsulfinyl-aktiviertemD-Glucal. Liebigs Ann Chem 1989, 1989, 429. <http://dx.doi.org/10.1002/jlac.198919890176>
  • Schmidt Richard R., Frische Klaus: De-novo-Synthese von Kohlenhydraten und verwandten Naturstoffen, 29. Synthese von partiell geschützten Zuckern ausmeso-Divinylglycol. Liebigs Ann Chem 1988, 1988, 209. <http://dx.doi.org/10.1002/jlac.198819880305>
  • Schmidt Richard R., Haag-Zeino Brigitte, Hoch Monika: De-novo-Synthese von Kohlenhydraten und verwandten Naturstoffen, 32 Die inverse Hetero-Diels-Alder-Reaktion zur Synthese von Teilsequenzen für Polyketid-Naturstoffe. Liebigs Ann Chem 1988, 1988, 885. <http://dx.doi.org/10.1002/jlac.198819880912>
  • Vogt Klaus, Schmidt Richard R.: Synthesis of (±)-ramulosin via inverse type hetero-diels-alder reaction 1. Tetrahedron 1988, 44, 3271. <http://dx.doi.org/10.1016/S0040-4020(01)85960-3>
  • Schmidt(rk) Richard R., Frick Wendelin: Short synthesis of c-aryl-glucopyranosides of the papulacandin type. Tetrahedron 1988, 44, 7163. <http://dx.doi.org/10.1016/S0040-4020(01)86084-1>
  • Hoppe Dieter, Tarara Gerhard, Wilckens Marcus, Jones Peter G., Schmidt Dieter, Stezowski John J.: Enantioselektive Synthese von Methylfuranosiden unnatürlicher 3,6-Didesoxy-3-methyl-aldohexosen aus Milchsäureestern durch Homoaldol-Reaktion. Angew Chem 1987, 99, 1079. <http://dx.doi.org/10.1002/ange.19870991033>
  • Schmidt Richard R., Preuss Rainer, Betz Rainer: C-1 lithiation of c-2 activated glucals. Tetrahetron Lett 1987, 28, 6591. <http://dx.doi.org/10.1016/S0040-4039(00)96921-1>
  • Schmidt Richard R., Frick Wendelin, Haag-Zeino Brigitte, Apparao Satyam: C-aryl-glycosides and 3-deoxy-2-glyculosonates via inverse type hetero-diels-alder reaction. Tetrahetron Lett 1987, 28, 4045. <http://dx.doi.org/10.1016/S0040-4039(01)83857-0>