Crich Publications 2005 2004 2003 2002
Crich Publications 1983-2001

2005

  • 6-O-Benzyl and 6-O-Silyl-N-acetyl-2-amino-2-N,3-O-carbonyl-2-deoxyglucosides: Effective Glycosyl Acceptors in the Glucosamine 4-OH Series.  Effect of Anomeric Stereochemistry on the Removal of the Oxazolidinone Group, D. Crich and A. U. Vinod, J. Org. Chem. 2005, 70, in press.
  • Disarming, Non-participating 2-O-Protecting Groups in Manno- and Rhamnopyranosylation: Scope and Limitations of Sulfonates, Vinylogous Esters, Phosphates, Cyanates, and Nitrates, D. Crich, T. K. Hutton, A. Banerjee, P. Jayalath, and J. Picione,Tetrahedron: Asymmetry 2005, 16, 105.
  • Direct Synthesis of Heterobiaryls by Radical Addition to Pyridine: Expeditious Synthesis of Chelating Ligands, D. Crich and M. Patel, Heterocycles 2005, 65, in press.

2004

  • Mechanism of 4,6-O-Benzylidene Directed β-Mannosylation as Determined by α-Deuterium Kinetic Isotope Effects, D. Crich and N. S. Chandrasekera, Angew. Chem. Int. Ed. Engl. 2004, 43, 5386-5389.
  • Design, Synthesis and Evaluation of Oxyanion-Hole Selective Inhibitor Substituents for the S1 Subsite of Factor Xa, S. Rumthao, O. Lee, Q. Sheng, WT. Fu, D. C. Mulhearn, D. Crich, A. D. Mesecar, and M. E. Johnson. Bioorg. Med. Chem. Lett. 2004, 14, 5165-5170.
  • Direct Chemical Synthesis of the β-Mannans: Linear and Block Syntheses of the Alternating β-(1→3)-β-(1→4)-Mannan Common to Rhodotorula glutinis, Rhodotorula mucilaginosa, and Leptospira biflexa, D. Crich, W. Li and H. Li, J. Am. Chem. Soc. 2004, 126, 15081-15086.
  • Direct Chemical Synthesis of the β-D-Mannans: the β-(1→2)- and β-(1→4)-Series, D. Crich, A. Banerjee and Q. Yao, J. Am. Chem. Soc. 2004, 126, 14930-14934.
  • Structure and Distribution of Branched Aliphatic Alkanes with Quaternary Carbon Atoms in Cenomanian and Turonian Black Shales of Pasquia Hill (Saskatchewan, Canada), F. Kenig, D.-J. H. Simons, D. Crich, J. P. Cowen, G. T. Ventura and T. Rehbein-Khalily, Organic Geochem. 2005, 36, 117-138.
  • The Benzylidene Acetal Fragmentation Route to 6-Deoxy Sugars: Direct Reductive Cleavage in the Presence of Ether Protecting Groups Permitting the Efficient, Highly Stereocontrolled Synthesis of β-D-Rhamnosides from D-Mannosyl Glycosyl Donors.  Total Synthesis of α-D-Gal-(1→3)-α-D-Rha-(1→3)-β-D-Rha-(1→4)-β-D-Glu-OMe, the Repeating Unit of the Antigenic Lipopolysaccharide from Escherichia hermannii ATCC 33650 and 33652, D. Crich and Q. Yao. J. Am. Chem. Soc. 2004, 126, 8232-8236.
  • Endo-Selective Quenching of Hexahydropyrrolo[2,3-b]indole-based N-Acyliminium Ions, R. L. Meza-León, D. Crich, S. Bernès, and L. Quintero, J. Org. Chem. 2004, 69, 3976-3978.
  • Glycosylation with Sulfoxides and Sulfinates as Donors or Promoters, D. Crich and L. B. L. Lim, Org. React. 2004, 64, 115-251.
  • The Intramolecular Asymmetric Pauson-Khand Cyclization as a Novel and General Stereoselective Route to Benzindene Prostacyclins: Synthesis of UT-15 (Treprostinil), R. M. Moriarty, N. Rani, L. A. Enache, M. S. Rao, H. Batra, L. Guo, R. A. Penmasta, J. P. Staszewski, S. M. Tuladhar, O. Prakash, D. Crich, A. Hirtopeanu, and R. Gilardi, J. Org. Chem. 2004, 69, 1890-1902.
  • Catalytic Allylic Oxidation with a Recyclable, Fluorous Seleninic Acid, D. Crich and Y. Zou, Org. Lett. 2004, 6, 775-777
  • Synthesis of Carbazomycin B by Radical Arylation of Benzene, D. Crich and S. Rumthao, Tetrahedron, 2004, 60, 1513-1516.
  • Cyclofunctionalization of Unsaturated Alcohols, Phenols, Acids, and Sulfonamides with 1-Benzenesulfinyl Piperidine and Trifluoromethanesulfonic Anhydride, D. Crich, B. Surve, and M. Sannigrahi, Heterocycles, 2004, 62, 827-830.

2003

  • Enantioselective Cyclization of Alkene Radical Cations, D. Crich, M. Shirai, and S. Rumthao, Org. Lett. 2003, 5, 3767-3769.
  • The 3,4-O-Carbonate Protecting Group as a β-Directing Group in Rhamnopyranosylation in both Homogeneous and Heterogeneous Glycosylations as Compared to the Chameleon-Like 2,3-O-Carbonates, D. Crich, A. U. Vinod, and J. Picione, J. Org. Chem. 2003, 68, 8453-8458.
  • Influence of the 4,6-O-Benzylidene, 4,6-O-Phenylboronate, and 4,6-O-Polystyrylboronate Protecting Groups on the Stereochemical Outcome of Thioglycoside-Based Glyocsylations Mediated by 1-Benzenesulfinyl Piperidine/Triflic Anhydride and N-Iodosuccinimide/Trimethylsilyl Triflate, D. Crich, M. de la Mora, A. U. Vinod, J. Org. Chem. 2003, 68, 8142-8148.
  • The β-Acyloxy)alkyl Radical Rearrangement Revisited, D. Crich and D.-H. Suk, Can. J. Chem. 2004, 82, 75-79.
  • Branched Aliphatic Akanes with Quaternary Substituted Carbon Atoms in Modern and Ancient Geologic Samples, F. Kenig, D.-J. H. Simons, D. Crich, J. P. Cowen, G. T. Ventura, T. Rehbein-Khalily, T. C. Brown, and K. B. Anderson, Proc. Natl. Acad. Sci. 2003, 100, 12554-12558.
  • Borane-Fluorous Dialkyl Sulfide.  Preparation and Application to the Hydroboration of β-Pinene, D. Crich, M. Patel, and S. Neelamkavil in Handbook of Fluorous Chemistry, J. A. Gladysz, I. T. Horváth, and D. P. Curran, Eds, Wiley-VCH, Weinheim, 2004, 475-477.
  • Recyclable Oxidation Reagents, D. Crich and Y. Zou in Handbook of Fluorous Chemistry, J. A. Gladysz, I. T. Horváth, and D. P. Curran, Eds, Wiley-VCH, Weinheim, 2004, 202-222.
  • 1-Benzenesulfinyl Piperidine (BSP)/Triflic Anhydride: an Effective Combination for the Hydrolysis of Dithioacetals, D. Crich and J. Picione, Synlett 2003, 1257-1258.
  • Tandem Polar/Radical Crossover Sequences for the Formation of Fused and Bridged Bicyclic Nitrogen Heterocycles Involving Radical Ionic Chain Reactions, and Alkene Radical Cation Intermediates, Performed under Reducing Conditions: Scope and Limitations, D. Crich, K. Ranganathan, S. Neelamkavil and X. Huang, J. Am. Chem. Soc. 2003, 125, 7942-7947.
  • Highly Diastereoselective Radical Cyclization of a Glucose-Derived Enol Ether Radical Cation/Phosphate Anion Pair, D. Crich, D.-H. Suk and S. Sun, Tetrahedron: Asymmetry 2003, 14, 2861-2864.
  • The 4,6-O-[α-(2-(2-Iodophenyl)ethylthiocarbonyl)-benzylidene] Protecting Group: Stereoselective Glycosylation, Reductive Radical Fragmentation, and the Synthesis of β-D-Rhamnopyranosides and Other Deoxy Sugars, D. Crich and Q. Yao, Org. Lett. 2003, 5, 2189-2191.
  • Design and Synthesis of Highly Constrained Factor Xa Inhibitors: Amidine-Substituted Bis(benzoyl)-[1,3]-diazpan-2-ones and Bis(benzylidene)-bis(gem-dimethyl)cycloketones, J. Cui, D. Crich, D. Wink, M. Lam, A. L. Rheingold, D. A. Case, W. T. Fu, Y. Zhou, M. Rao, A. J. Olson, and M. E. Johnson, Bioorg. Med. Chem., 2003, 11, 3379-3392.
  • Oxazolidinone Protection of N-Acetylglucosamine Confers High Reactivity on the 4-Hydroxy Group in Glycosylation, D. Crich and A. U. Vinod, Org. Lett. 2003, 5, 1297-1300.
  • Direct Synthesis of the β-L-Rhamnopyranosides, D. Crich and J. Picione, Org. Lett. 2003, 5, 781-784.
  • A Short Synthesis of the Trisaccharide Building Block of the N-Linked Glycans, V. Y. Dudkin and D. Crich, Tetrahedron Lett. 2003, 44, 1787-1789.
  • Asymmetric Synthesis of Highly-Substituted β-Nitroalcohols and Enantiomerically-Enriched 4,4,5-Trisubstituted Oxazolidinones,D. Crich, K. Ranganathan, S. Rumthao, and M. Shirai, J. Org. Chem. 2003, 68, 2034-2037

2002

  • Chemistry of Glycosyl Triflates: Synthesis of b-Mannopyranosides, D. Crich, J. Carbohydr. Chem. 2002, 21, 663-686.
  • Fluorous Dimethyl Sulfide: A Convenient, Odorless, Recyclable Borane Carrier, D. Crich and S. Neelamkavil, Org. Lett. 2002, 4, 4175-4177.
  • Diastereoselectivity in the Cyclization of Alkene Radical Cations: Contact Ion Pairs and Memory Effects, D. Crich and K. Ranganathan, J. Am. Chem. Soc, 2002, 124, 12422-12423.
  • Generation and Trapping of Alkene Radical Cations under Non-Oxidizing Conditions: Formation of Six-Membered Rings by exo- and endo-Mode Cyclizations, D. Crich and S. Neelamkavil, Org. Lett. 2002, 4, 2573-2575.
  • The Effect of the Base in the Fragmentation of Nucleotide C4’ Radicals, D. Crich, D.-H. Suk, and X. Hao, Tetrahedron, 2002, 58, 5789-5801.
  • Solid Phase Synthesis of b-Mannosides, D. Crich and M. Smith, J. Am. Chem. Soc., 2002, 124,8867-8869.
  • Radical Contraction of 1,3,2-Dioxaphosphepanes to 1,3,2-Dioxaphosphorinanes: a Kinetic and 17O-NMR Spectroscopic Study, D. Crich, F. Sartillo-Piscil, L. Quintero-Cortes, and D. J. Wink, J. Org. Chem., 2002, 67, 3360-3364.
  • Rapid Assembly of Tetrahydrodibenzofurans and Tetrahydrocarbazoles from Benzene and o-Iodophenols and o-Iodoanilines: Reductive Radical Arylation of Benzene in Action, D. Crich and M. Sannigrahi, Tetrahedron, 2002, 58, 3319-3322.
  • Stereoselective Formation of Glycosyl Sulfoxides and Their Subsequent Equilibration.  Ring Inversion of an a-Xylopyranosyl Sulfoxide Dependent on the Configuration at Sulfur, D. Crich, J. Mataka, L. N. Zakharov, A. L. Rheingold, and D. J. Wink, J. Am. Chem. Soc. 2002, 124, 6028-6036.
  • Confirmation of the Connectivity of 4,8,12,16,20-Pentamethylpentacosylphosphoryl b-D-Mannopyranoside, an Unusual  b-Mannosyl Phosphoisoprenoid from mycobacterium avium, through Synthesis, D. Crich and V. Dudkin, J. Am. Chem. Soc. 2002, 124, 2263-2266.
  • The Fluorous Swern and Corey-Kim Reactions: Scope and Mechanism, D. Crich and S. Neelamkavil, Tetrahedron, 2002, 58, 3865-3870.
  • Synthesis of the Mannosyl Erythritol Lipid MEL A: Confirmation of the Configuration of the “meso-Erythritol”, D. Crich, M. A. de la Mora and R. Cruz, Tetrahedron, 2002, 58, 35-44.
  • Synthesis of the Salmonella Type E1 Core Trisaccharide as a Probe for the Generality of 1-Benzenesulfinyl Piperidine/Triflic Anhydride Combination for Glycosidic Bond Formation from Thioglycosides, D. Crich and H. Li, J. Org. Chem., 2002, 67, 4640-4646.
  • An Oxyanion-Hole Selective Serine Protease Inhibitor in Complex with Trypsin, J. Cui, F. Marankan, W. Fu, D. Crich, A. Mesecar and M. E. Johnson, Bioorg. Med. Chem., 2002, 10, 41-46.

Crich Publications 1983-2001