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Pure Appl. Chem., 1978, Vol. 50, No. 11-12, pp. 1343-1362

http://dx.doi.org/10.1351/pac197850111343

Sugar enolones: synthesis, reactions of preparative interest, and γ-pyrone formation

F. W. Lichtenthaler

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  • Hussain Altaf, Mukherjee Debaraj: Highly diastereoselective 1,2-dichlorination of glycals using NCS/PPh3: study of substituent and solvent effects. Tetrahedron 2014, 70, 1133. <http://dx.doi.org/10.1016/j.tet.2013.12.088>
  • Xavier Nuno M., Rauter Amélia P.: Environmentally friendly approaches to the synthesis of new antibiotics from sugars. PureAppl Chem 2012, 1. <http://dx.doi.org/10.1351/PAC-CON-11-11-11>
  • Jarglis Pan, Göckel Volker, Lichtenthaler Frieder W.: A convenient access to the 1,5-anhydro forms of d-tagatose, l-rhamnulose and d-xylulose via 2-hydroxyglycal esters. Tet Asymm 2009, 20, 952. <http://dx.doi.org/10.1016/j.tetasy.2009.03.016>
  • Xavier Nuno M., Rauter Amélia P.: Sugars containing α,β-unsaturated carbonyl systems: synthesis and their usefulness as scaffolds in carbohydrate chemistry. Carbohydrates Research 2008, 343, 1523. <http://dx.doi.org/10.1016/j.carres.2008.04.033>
  • Brehm Manfred, Göckel Volker H., Jarglis Pan, Lichtenthaler Frieder W.: Expedient conversion of d-glucose into 1,5-anhydro-d-fructose and into single stereogenic-center dihydropyranones, suitable six-carbon scaffolds for concise syntheses of the soft-coral constituents (−)-bissetone and (−)-palythazine. Tet Asymm 2008, 19, 358. <http://dx.doi.org/10.1016/j.tetasy.2008.01.019>
  • Gupta Preeti, Kumari Nitee, Agarwal Aditi, Vankar Yashwant D.: HClO4·SiO2 catalysed synthesis of alkyl 3-deoxy-hex-2-enopyranosides from 2-hydroxy glucal ester: application in the synthesis of a cis-fused bicyclic ether and a 4-amino-C-glucoside. Org Biomol Chem 2008, 6, 3948. <http://dx.doi.org/10.1039/b810654a>
  • Jarglis Pan, Lichtenthaler Frieder W.: Eine stereospezifische Synthese von (S,S)-Palythazin aus D-Glucose. Angew Chem 2006, 94, 140. <http://dx.doi.org/10.1002/ange.19820940219>
  • Sagar Ram, Reddy L. Vijaya Raghava, Shaw Arun K.: Studies on epoxidation of enantiomerically pure 2,3-dideoxy hex-2-enitols: a convenient access to highly functionalized enantiomerically pure tetrahydrofuran derivatives. Tet Asymm 2006, 17, 1189. <http://dx.doi.org/10.1016/j.tetasy.2006.04.022>
  • Deppe Olaf, Glümer Anke, Yu Shukun, Buchholz Klaus: Synthesis and co-polymerization of an unsaturated 1,5-anhydro-d-fructose derivative. Carbohydrates Research 2004, 339, 2077. <http://dx.doi.org/10.1016/j.carres.2004.06.007>
  • Boettcher Andrea, Lichtenthaler Frieder W.: d-Fructose- and l-sorbose-derived endo- and exo-hydroxyglycal esters and some of their chemistry. Tet Asymm 2004, 15, 2693. <http://dx.doi.org/10.1016/j.tetasy.2004.07.018>
  • Rauter Amélia P., Canda Tana, Justino Jorge, Ismael Maria I., Figueiredo José A.: Synthesis of Phenylseleno Sugars from Epoxides and of α,β‐Unsaturated Carbonyl Derivatives for the Study of Their Insecticidal Activity. J Carbohydr Chem 2004, 23, 239. <http://dx.doi.org/10.1081/CAR-200030077>
  • Lichtenthaler Frieder W., Klotz Jürgen, Nakamura Katsumi: (−)-Daucic acid: Proof of d-lyxo configuration, synthesis of its d-ribo, d-xylo, l-arabino and l-lyxo analogs, and biosynthetic implications. Tet Asymm 2003, 14, 3973. <http://dx.doi.org/10.1016/j.tetasy.2003.10.007>
  • Liu Junjie, Huang Cheng-Yuan, Wong Chi-Huey: An efficient method for the preparation of 2-hydroxy- and 2-aminoglycals from glycosyl sulfoxides. Tetrahetron Lett 2002, 43, 3447. <http://dx.doi.org/10.1016/S0040-4039(02)00555-5>
  • Majetich George, Zhang Yong, Dreyer Geoffrey: A convenient synthesis of di- and trisubstituted γ-pyrones. Tetrahedron Letters 1993, 34, 449. <http://dx.doi.org/10.1016/0040-4039(93)85099-I>
  • Hanessian Stephen, Girard Christian, Chiara Jose Luis: A practical synthesis of 2-deoxy aldonolactones via a SmI2-mediated α-deoxygenation reaction. Tetrahedron Letters 1992, 33, 573. <http://dx.doi.org/10.1016/S0040-4039(00)92313-X>
  • Lichtenthaler Frieder W., Lindner Hans J.: On the extent of chair distortion in “tetra-axial” derivatives of 2,3,4-tri-O-benzoyl-β-d-xylopyranose. Carbohydrates Research 1990, 200, 91. <http://dx.doi.org/10.1016/0008-6215(90)84184-V>
  • Lichtenthaler Frieder W., Nishiyama Shigeru, Weimer Thomas: Enantiomerically Pure Building Blocks from Sugars, 10 2,3-Dihydropyranones with Contiguous Chiral Centers: Practical Routes for Their Aquisition and Evaluation of their Reaction Potential. Liebigs Ann Chem 1989, 1989, 1163. <http://dx.doi.org/10.1002/jlac.198919890288>
  • Chirale Bausteine aus Kohlenhydraten. Nachr Chem Tech Lab 1987, 35, 1155. <http://dx.doi.org/10.1002/nadc.19870351110>
  • Varela Oscar, de Fina Griselda M., de Lederkremer Rosa M.: The reaction of 2-hydroxyglycal esters with alcohols in the presence of N-iodosuccinimide, stereoselective synthesis of α anomers of alkyl 3-deoxyhex-2-enopyranosides and 3,4-dideoxyhex-3-enopyranosid-2-uloses. Carbohydrates Research 1987, 167, 187. <http://dx.doi.org/10.1016/0008-6215(87)80278-1>
  • Klemer Almuth, Wilbers Hubert: Enolate von Kohlenhydraten, 4. Axiale α-C-Alkylierung von α-Amino-α-desoxy-Kohlenhydratulosen. Liebigs Ann Chem 1985, 1985, 2328. <http://dx.doi.org/10.1002/jlac.198519851204>
  • Lichtenthaler Frieder W., Doleschal Walter, Hahn Susanne: Studies on Ketoses, 2. Spirocyclic Dihydropyranones from D-Fructose. Liebigs Ann Chem 1985, 1985, 2454. <http://dx.doi.org/10.1002/jlac.198519851214>
  • Klausener Alexander, Runsink Jan, Scharf Hans-Dieter: Reactions of partially acylated aldohexopyranosides: A contribution to the preparation and chemistry of 3,2-enolones. Carbohydrates Research 1985, 138, 335. <http://dx.doi.org/10.1016/0008-6215(85)85117-X>
  • Lichtenthaler Frieder W., Nishiyama Shigeru, Köhler Peter, Lindner Hans J.: Anomeric stereocontrol in addition reactions to hexose-derived dihydropyranones. Carbohydrates Research 1985, 136, 13. <http://dx.doi.org/10.1016/0008-6215(85)85182-X>
  • Kunz Horst, Weißmüller Joachim: Synthese des Methylethers der Herzgift-Methylreduktinsäure ausD-Glucose. Liebigs Ann Chem 1984, 1984, 66. <http://dx.doi.org/10.1002/jlac.198419840108>
  • Köll Peter, Klenke Kurt, Eisermann Doris: Darstellung Der Isomeren 1,6-DI-O-Acetyl-3,4-Didesoxy-α, β-D-Glycero-Hex-3-Enopyrahos-2-Ulosen. J Carbohydr Chem 1984, 3, 403. <http://dx.doi.org/10.1080/07328308408057905>
  • Ried Walter, Broft Gert W.: Synthese vonN-Cyandithiocarbimidsäure-Abkömmlingen. Liebigs Ann Chem 1983, 1983, 274. <http://dx.doi.org/10.1002/jlac.198319830212>
  • Kunz Horst, Weiß;müller Joachim: Synthese von 2-Acyloxy- und 2-Alkyloxy-3-ketoglycalen und ihren Bromaddukten. Liebigs Ann Chem 1983, 1983, 1561. <http://dx.doi.org/10.1002/jlac.198319830912>
  • Lichtenthaler Frrieder W., Jarglis Pan, Hempe Walter: Sugar enolones, XVIII. stereocontrolled functionalization at proanomeric centres by photobromination. – A novel efficient access to oxo- and oximinoglycosyl bromides. Liebigs Ann Chem 1983, 1983, 1959. <http://dx.doi.org/10.1002/jlac.198319831111>
  • Lichtenthaler Frrieder W., Löhe Albert, Cuny Ecxkehard: Sugar enolones, XIX. An approach to actinospectose-type 2,3-diketo sugars. – Synthetic proof for theR configuration of “Herzgift-Methylreduktinsäure”. Liebigs Ann Chem 1983, 1983, 1973. <http://dx.doi.org/10.1002/jlac.198319831112>
  • Baggett Neil, Marsden Brian J.: Synthesis of 4-nitrophenyl 2,3,6-tri-O-acetyl-4-deoxy-β-d-lyxo-hexopyranoside and a new synthesis of 4-nitrophenyl β-d-mannopyranoside. Carbohydrates Research 1983, 119, 285. <http://dx.doi.org/10.1016/0008-6215(83)84067-1>
  • Jarglis Pan, Lichtenthaler Frieder W.: Stereospecific Synthesis of (S,S)-Palythazine fromD-Glucose. Angew Chem Int Ed Engl 1982, 21, 141. <http://dx.doi.org/10.1002/anie.198201412>
  • Jarglis Pan, Lichtenthaler Frieder W.: A Stereospecific Synthesis ofS,S-Palythazine from D-Glucose. Angew Chem Int Ed Engl 1982, 21, 175. <http://dx.doi.org/10.1002/anie.198201750>
  • Hanessian Stephen, Tyler Peter C., Chapleur Yves: Reaction of lithium dimethylcuprate with conformationally biased β-acyloxy enol esters - regio and stereocontrolled access to functionalized six-carbon chiral synthons. Tetrahetron Lett 1981, 22, 4583. <http://dx.doi.org/10.1016/S0040-4039(01)82987-7>
  • Lichtenthaler Frieder W., Sakakibara Tohru, Egert Ernst: Sugar enolones, XI. 2-Halopentopyranosyl halides: Preparation, configurational elucidation, and conversion into enantiomeric dihydropyranones. Chem Ber 1980, 113, 471. <http://dx.doi.org/10.1002/cber.19801130207>
  • Lichtenthaler Frieder W., Jarglis Pan: Sugar enolones, XII. Peroxidation of pyranose-derived enol esters: An efficacious synthesis of peracetylhexosuloses and their conversion into γ-pyronesvia 3,2-enolones. Chem Ber 1980, 113, 489. <http://dx.doi.org/10.1002/cber.19801130208>
  • Heyns K., Feldmann J., Heyns K., Feldmann J.: Chemische Reaktionen und Derivatisierungen ungesättigter Zucker. Starch/Stärke 1980, 32, 40. <http://dx.doi.org/10.1002/star.19800320203>
  • Huynh-Dinh T., Gouyette C., Igolen J.: Cyano-1 ceto-3 et -4 L-rhamnoses. Tetrahetron Lett 1980, 21, 4499. <http://dx.doi.org/10.1016/S0040-4039(00)74533-3>
  • Lichtenthaler Frieder W., Jarglis Pan: Selective deacylation of enol esters with hydroxylamine. Tetrahetron Lett 1980, 21, 1425. <http://dx.doi.org/10.1016/S0040-4039(00)92736-9>
  • Lichtenthaler F.W., El Ashry E.S.H., Göckel V.H.: A convenient access to 1,5-anhydroketoses. Tetrahetron Lett 1980, 21, 1429. <http://dx.doi.org/10.1016/S0040-4039(00)92737-0>
  • Lichtenthaler Frieder W., Nishiyama Shigeru, Jarglis Pan: Neuartige, hochstereoselektive Umlagerungen chiraler Dihydropyranone. Angew Chem 1979, 91, 1001. <http://dx.doi.org/10.1002/ange.19790911210>
  • Lichtenthaler Frieder W., Nishiyama Shigeru, Jarglis Pan: Novel, Highly Stereoselective Rearrangements of Chiral Dihydropyranones. Angew Chem Int Ed Engl 1979, 18, 936. <http://dx.doi.org/10.1002/anie.197909361>