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Pure Appl. Chem., 2003, Vol. 75, No. 2-3, pp. 179-186

http://dx.doi.org/10.1351/pac200375020179

Synthesis of carbohydrate-based antibiotics

C.-H. Wong, M. C. Bryan, P. T. Nyffeler, H. Liu and Eli Chapman

Department of Chemistry, The Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, CA 9203, USA

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  • Itoh Susumu, Tokunaga Takuya, Sonoike Shotaro, Kitamura Masanori, Yamano Akihito, Aoki Shin: Asymmetric Aldol Reactions between Acetone and Benzaldehydes Catalyzed by Chiral Zn2+ Complexes of Aminoacyl 1,4,7,10-Tetraazacyclododecane: Fine-Tuning of the Amino-Acid Side Chains and a Revised Reaction Mechanism. Chem. Asian J. 2013, 8, 2125. <http://dx.doi.org/10.1002/asia.201300308>
  • Itoh Susumu, Tokunaga Takuya, Kurihara Masayuki, Aoki Shin: Asymmetric aldol reactions between cyclic ketones and benzaldehyde catalyzed by chiral Zn2+ complexes of aminoacyl 1,4,7,10-tetraazacyclododecane: effects of solvent and additives on the stereoselectivities of the aldol products. Tetrahedron: Asymmetry 2013, 24, 1583. <http://dx.doi.org/10.1016/j.tetasy.2013.10.009>
  • Patil Pratap S., Lee Chia-Chen, Huang Yu-Wen, Zulueta Medel Manuel L., Hung Shang-Cheng: Regioselective and stereoselective benzylidene installation and one-pot protection of d-mannose. Org. Biomol. Chem. 2013, 11, 2605. <http://dx.doi.org/10.1039/c3ob40079d>
  • Rale Madhura, Schneider Sarah, Sprenger Georg A., Samland Anne K., Fessner Wolf-Dieter: Broadening Deoxysugar Glycodiversity: Natural and Engineered Transaldolases Unlock a Complementary Substrate Space. Chem Eur J 2011, 17, 2623. <http://dx.doi.org/10.1002/chem.201002942>
  • Larionova Natalia A., Kucherenko Alexandr S., Siyutkin Dmitry E., Zlotin Sergei G.: (S)-Threonine/α,α-(S)-diphenylvalinol-derived chiral ionic liquid: an immobilized organocatalyst for asymmetric syn-aldol reactions. Tetrahedron 2011, 67, 1948. <http://dx.doi.org/10.1016/j.tet.2011.01.017>
  • 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>
  • Itoh Susumu, Kitamura Masanori, Yamada Yasuyuki, Aoki Shin: Chiral Catalysts Dually Functionalized with Amino Acid and Zn2+ Complex Components for Enantioselective Direct Aldol Reactions Inspired by Natural Aldolases: Design, Synthesis, Complexation Properties, Catalytic Activities, and Mechanistic Study. Chem Eur J 2009, 15, 10570. <http://dx.doi.org/10.1002/chem.200900733>
  • Markert Morris, Mahrwald Rainer: Total Syntheses of Carbohydrates: Organocatalyzed Aldol Additions of Dihydroxyacetone. Chem. Eur. J. 2008, 14, 40. <http://dx.doi.org/10.1002/chem.200701334>
  • Ramasastry S. S. V., Albertshofer Klaus, Utsumi Naoto, Tanaka Fujie, Barbas Carlos F.: Mimicking Fructose and Rhamnulose Aldolases: Organocatalyticsyn-Aldol Reactions with Unprotected Dihydroxyacetone. Angew Chem 2007, 119, 5668. <http://dx.doi.org/10.1002/ange.200701269>
  • Ramasastry S. S. V., Albertshofer Klaus, Utsumi Naoto, Tanaka Fujie, Barbas Carlos F.: Mimicking Fructose and Rhamnulose Aldolases: Organocatalyticsyn-Aldol Reactions with Unprotected Dihydroxyacetone. Angew Chem Int Ed 2007, 46, 5572. <http://dx.doi.org/10.1002/anie.200701269>
  • Tor Yitzhak: Targeting RNA with Small Molecules. Chem Eur J of Chem Bio 2003, 4, 998. <http://dx.doi.org/10.1002/cbic.200300680>
  • Wong Chi-Huey, Bryan Marian C., Nyffeler Paul T., Liu Haitian, Chapman Eli: Synthesis of Carbohydrate-Based Antibiotics. ChemInform 2003, 34. <http://dx.doi.org/10.1002/chin.200341255>