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Pure Appl. Chem., 1994, Vol. 66, No. 10-11, pp. 2135-2138

http://dx.doi.org/10.1351/pac199466102135

Novel methods for the synthesis of C-aryl glycoside natural products

K. A. Parker

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  • P. Hsung Richard, Tang Yu, Yang Jin-Haek, Liu Jia, Wang Chao-Chao, Lv Ming-Can, Wu Yi-Biao, Yu Xue-Liang, Ko Changhong: ASSEMBLY OF THE SOUTHERN MACROCYCLIC HALF OF (+)-SPIRASTRELLOLIDE A THROUGH CYCLIC ACETAL TETHERED RING-CLOSING METATHESIS AND 1,3-ANTI-MUKAIYAMA-ALDOL. HETEROCYCLES 2012, 86, 565. <http://dx.doi.org/10.3987/COM-12-S(N)54>
  • Figueroa Ruth, Feltenberger John B., Guevarra Christle C., Hsung Richard P.: Two remarkable epimerizations imperative for the success of an asymmetric total synthesis of (+)-aigialospirol. Sci China Chem 2011, 54, 31. <http://dx.doi.org/10.1007/s11426-010-4176-8>
  • Subrahmanyam Ayyagari V., Palanichamy Kalanidhi, Kaliappan Krishna P.: Application of an Enyne Metathesis/Diels-Alder Cycloaddition Sequence: A New Versatile Approach to the Syntheses of C-Aryl Glycosides and Spiro-C-Aryl Glycosides. Chem Eur J 2010, 16, 8545. <http://dx.doi.org/10.1002/chem.201000482>
  • PARKER K. A.: ChemInform Abstract: Novel Methods for the Synthesis of C-Aryl Glycoside Natural Products. ChemInform 2010, 26, no. <http://dx.doi.org/10.1002/chin.199507308>
  • P. Hsung Richard, Wang Jiashi, K. Ghosh Sunil, Wei Yonggang, B. Feltenberger John: A Cyclic Acetal Tethered Intramolecular Diels-Alder Cycloaddition. Studies Directed toward a Total Synthesis of (±)-Fusidilactone C. HETEROCYCLES 2010, 82, 1379. <http://dx.doi.org/10.3987/COM-10-S(E)93>
  • Gómez Ana M., Pedregosa Ana, Casillas Marta, Uriel Clara, López J. Cristóbal: Synthesis of C-1 Alkyl and Aryl Glycals from Pyranosyl or Furanosyl Chlorides by Treatment with Organolithium Reagents. Eur J Org Chem 2009, 2009, 3579. <http://dx.doi.org/10.1002/ejoc.200900417>
  • Gómez Ana M., Pedregosa Ana, Barrio Aitor, Valverde Serafín, López J. Cristóbal: Synthesis of Furanosyl C-1 Glycals through Palladium-Catalyzed Reactions of a Furanosyl 2,3-Anhydro-exo-glycal. Eur J Org Chem 2009, 2009, 4627. <http://dx.doi.org/10.1002/ejoc.200900585>
  • Yamamoto Yoshihiko, Yamashita Ken, Hotta Tomitaka, Hashimoto Toru, Kikuchi Makoto, Nishiyama Hisao: Synthesis of SpirocyclicC-Arylglycosides and -Ribosides by Ruthenium-Catalyzed Cycloaddition. Chem Asian J 2007, 2, 1388. <http://dx.doi.org/10.1002/asia.200700077>
  • Ko Changhong, Hsung Richard P.: An unusual stereoselectivity in the anomeric substitution with carbamates promoted by HNTf2. Org Biomol Chem 2007, 5, 431. <http://dx.doi.org/10.1039/b615725d>
  • Ghosh Sunil K., Ko Changhong, Liu Jia, Wang Jiashi, Hsung Richard P.: A ketal-tethered RCM strategy toward the synthesis of spiroketal related natural products. Tetrahedron 2006, 62, 10485. <http://dx.doi.org/10.1016/j.tet.2006.06.113>
  • Parker Kathlyn A., Mindt Thomas L., Koh Yung-hyo: TESOTf-Induced Rearrangement of Quinols. Efficient Construction of the Fully Functionalized Carbon Skeleton of the Griseusins by a Divergent−Reconvergent Approach. Org Lett 2006, 8, 1759. <http://dx.doi.org/10.1021/ol060206q>
  • Yamamoto Yoshihiko, Hashimoto Toru, Hattori Kozo, Kikuchi Makoto, Nishiyama Hisao: Synthesis of Spirocyclic C-Arylribosides via Cyclotrimerization. Org Lett 2006, 8, 3565. <http://dx.doi.org/10.1021/ol061350e>
  • Parker Kathlyn A., Su Dai‐Shi: The “Reverse Polarity” Approach to Ravidomycin. Aryl C‐Aminoglycosides from a Lithiated Aminoglycal. J Carbohydr Chem 2005, 24, 187. <http://dx.doi.org/10.1081/CAR-200059957>
  • Berry Craig R., Hsung Richard P.: Inverse electron-demand aza-[4+2] cycloaddition reactions of allenamides. Tetrahedron 2004, 60, 7629. <http://dx.doi.org/10.1016/j.tet.2004.05.117>
  • Ghosh Sunil K, Hsung Richard P, Wang Jiashi: Ketal-tethered ring-closing metathesis. An unconventional approach to constructing spiroketals and total synthesis of an insect pheromone. Tetrahedron Letters 2004, 45, 5505. <http://dx.doi.org/10.1016/j.tetlet.2004.05.017>
  • Parker Kathlyn A., Chang Wonsuk: A Synthesis of l-Vancosamine Derivatives from Non-Carbohydrate Precursors by a Short Sequence Based on the Marshall, McDonald, and Du Bois Reactions. Org Lett 2003, 5, 3891. <http://dx.doi.org/10.1021/ol035479p>
  • Koikov Leonid N, Smoliakova Irina P, Liu Hui: One-pot synthesis of C-glycosylic compounds (C-glycosides) from d-glucal, p-tolylsulfenyl chloride and aromatic/heteroaromatic compounds in the presence of Lewis acids. Carbohydrates Research 2002, 337, 1275. <http://dx.doi.org/10.1016/S0008-6215(02)00123-4>
  • Spencer Roxanne P, Schwartz Jeffrey: Titanium(III) Reagents in Carbohydrate Chemistry: Glycal and C-Glycoside Synthesis. Tetrahedron 2000, 56, 2103. <http://dx.doi.org/10.1016/S0040-4020(99)01088-1>
  • Parker Kathlyn A., Georges Asimina T.: Reductive Aromatization of Quinols:  Synthesis of the C-Arylglycoside Nucleus of the Papulacandins and Chaetiacandin. Org Lett 2000, 2, 497. <http://dx.doi.org/10.1021/ol991346l>
  • Khan Abu T., Ahmed Wasim, Schmidt Richard R.: A method for the synthesis of C-(2-deoxy-β-glycosyl) arenes. Carbohydrates Research 1996, 280, 277. <http://dx.doi.org/10.1016/0008-6215(95)00321-5>