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Pure Appl. Chem., 1981, Vol. 53, No. 1, pp. 129-148

http://dx.doi.org/10.1351/pac198153010129

Studies directed toward the total synthesis of the ezomycins, the octosyl acids and related antibiotics

S. Hanessian, D. M. Dixit and T. J. Liak

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  • Pesic Alexander, Steinhaus Britta, Kemper Sebastian, Nachtigall Jonny, Kutzner Hans Jürgen, Höfle Gerhard, Süssmuth Roderich D: Isolation and structure elucidation of the nucleoside antibiotic strepturidin from Streptomyces albus DSM 40763. J Antibiot 2014. <http://dx.doi.org/10.1038/ja.2014.16>
  • Thota V. Narasimharao, Gervay-Hague Jacquelyn, Kulkarni Suvarn S.: Synthesis of β-C-galactosyl d- and l-alanines. Org. Biomol. Chem. 2012, 10, 8132. <http://dx.doi.org/10.1039/c2ob26078f>
  • Mukherjee Subhrangshu, Mandal Sukhendu B., Bhattacharjya Anup: Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides. RSC Adv. 2012, 2, 8969. <http://dx.doi.org/10.1039/c2ra20689g>
  • 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>
  • Hanessian Stephen: Structure-Based Organic Synthesis of Drug Prototypes: A Personal Odyssey. ChemMedChem 2006, 1, 1300. <http://dx.doi.org/10.1002/cmdc.200600203>
  • Cervi Giovanni, Peri Francesco, Battistini Carlo, Gennari Cesare, Nicotra Francesco: Bicyclic carbohydrate-derived scaffolds for combinatorial libraries. biorg med chem 2006, 14, 3349. <http://dx.doi.org/10.1016/j.bmc.2005.12.055>
  • Knapp Spencer, Thakur Vinay V., Madduru Machender R., Malolanarasimhan Krishnan, Morriello Gregori J., Doss George A.: Short Synthesis of Octosyl Nucleosides. Org Lett 2006, 8, 1335. <http://dx.doi.org/10.1021/ol0600382>
  • Hanessian Stephen, Marcotte Stéphane, Machaalani Roger, Huang Guobin: Total Synthesis and Structural Confirmation of Malayamycin A:  A Novel Bicyclic C-Nucleoside from Streptomyces malaysiensis. Org Lett 2003, 5, 4277. <http://dx.doi.org/10.1021/ol030095k>
  • Gumina Giuseppe, Chu Chung K.: Synthesis of l-Oxetanocin. Org Lett 2002, 4, 1147. <http://dx.doi.org/10.1021/ol025562x>
  • Mukherjee Ali, Palcic Monica M., Hindsgaul Ole: Synthesis and enzymatic evaluation of modified acceptors of recombinant blood group A and B glycosyltransferases. Carbohydrates Research 2000, 326, 1. <http://dx.doi.org/10.1016/S0008-6215(00)00003-3>
  • Dorta Rosa L., Martín Angeles, Salazar JoséA., Suárez Ernesto, Prangé Thierry: Synthesis of dispiroacetals from carbohydrates by intramolecular hydrogen abstractions. Tetrahetron Lett 1996, 37, 6021. <http://dx.doi.org/10.1016/0040-4039(96)01265-8>
  • Lassaletta José M., Meichle Michaela, Weiler Sven, Schmidt Richard R.: Silyl Group Migration in 1-O-Silyl Protected Sugars-Convenient Synthesis of 2-O-Unprotected Sugars. J Carbohydr Chem 1996, 15, 241. <http://dx.doi.org/10.1080/07328309608005442>
  • Fattori Daniela, Vogel Pierre: Highly stereoselective, total synthesis of β-c-hexopyranosyl derivatives. Tetrahetron Lett 1993, 34, 1017. <http://dx.doi.org/10.1016/S0040-4039(00)77480-6>
  • 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>
  • Toshima Kazunobu, Nozaki Yuko, Tatsuta Kuniaki: Highly stereoselective glycosylation by conformational assistance of glycosyl donor. Tetrahetron Lett 1991, 32, 6887. <http://dx.doi.org/10.1016/0040-4039(91)80435-9>
  • Toshima Kazunobu, Mukaiyama Satsuki, Yoshida Takehito, Tamai Tetsuro, Tatsuta Kuniaki: Application of efficient glycosylation of 2,6-anhydro-2-thio sugar to the total synthesis of erythromycin A. Tetrahetron Lett 1991, 32, 6155. <http://dx.doi.org/10.1016/0040-4039(91)80777-4>
  • 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>
  • Toshima Kazunobu, Mukaiyama Satsuki, Ishiyama Takashi, Tatsuta Kuniaki: The use of 2,6-anhydro-2-thio sugar for a highly stereocontrolled glycosylation: A novel strategy for synthesis of 2,6-dideoxy-α-glycosides. Tetrahetron Lett 1990, 31, 3339. <http://dx.doi.org/10.1016/S0040-4039(00)89059-0>
  • Spohr Ulrike, Lemieux Raymond U.: Synthetic, conformational, and immunochemical studies of modified Lewis b and Y human blood-group determinants to serve as probes for the combining site of the lectin IV of Griffonia simplicifolia. Carbohydrates Research 1988, 174, 211. <http://dx.doi.org/10.1016/0008-6215(88)85093-6>
  • Nakahara Yoshiaki, Fujita Akira, Beppu Kazuo, Ogawa Tomoya: Total synthesis of antibiotic A23187 (calcimycin) from D-glucose. Tetrahedron 1986, 42, 6465. <http://dx.doi.org/10.1016/S0040-4020(01)88109-6>
  • Inch T.D.: Formation of convenient chiral intermediates from carbohydrates and their use in synthesis. Tetrahedron 1984, 40, 3161. <http://dx.doi.org/10.1016/0040-4020(84)85002-4>