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Publications

PUBLICATIONS

  1.  Zewge, D.; Gosselin, F.; Sidler, R.; DiMichele, L.; Cvetovich, R. “A Safe and Practical Procedure for Global Deprotection of Oligoribonucleotides” J. Org. Chem. 2010, 75, 5305.
  2. Cvetovich, R. J. “Hydrogen Peroxide Oxidation of Phosphite Triesters in Oligonucleotide Syntheses” Org. Process Res. Dev. 2009, 14, 295.
  3. Chung, J.; Hartner, F.; Cvetovich, R. “Synthesis development of an aminomethylcycline antibiotic via an electronically tuned acyliminium Friedel-Crafts reaction”, Tetrahedron Lett. 2008, 49, 6095.
  4. Savarin, C.; Chung, J.; Murry, J. A.; Cvetovich, R. J.; McWilliams, C.; Hughes, D.; Amato, J.; Boice, G.; Conrad, K.; Corley, E.; Reamer, R.; DiMichele, L.   “An efficient and scalable process for the preparation of a potent MC4 receptor agonist”, Process Chemistry in the Pharmaceutical Industry (2008), 65-87.
  5. Chung, J.; Cvetovich, R. J. “Synthesis Development of a Naphthyridone p38 MAP Kinase Inhibitor”, Current Opinions in Drug Discovery and Development 2006, 9, 792.
  6. Natarajan, S. R.; Liu, L.; Levorse, M.; Thompson, J. E.; O’Neill, E. A.; O’Keefe, S. J.; Vora, K. A.; Cvetovich, R.; Chung, J. Y.; Carballo-Jane, E. and Visco, D. M. “p38 MAP kinase inhibitors. Discovery of an orally bioavailable and highly efficacious compound based on the 7-amino-naphthyridone scaffold”, Bioorganic & Medicinal Chemistry Letters 2006, 16(20), 5468.
  7. Chung, J.; Cvetovich, R. J.; McLaughlin, M.; Amato, J.; Tsay, F.-R.; Jensen, M.; Weissman, S. and Zewge, D. “Synthesis of a Naphthyridone p38 MAP Kinase Inhibitor”, J. Org. Chem. 2006, 71, 8602.
  8. Cvetovich, R.*; Reamer, R.; DiMichele, L.; Chung, J.; and Chilenski, J. “Unique Tandem Heck-Lactamization Naphthyridinone Ring Formation between Acrylanilides and Halogenated Pyridines”, J. Org. Chem. 2006, 71, 8610.
  9. Cvetovich, R.; DiMichele, L. “Formation of Acrylanilides, Acrylamides, and Amides Directly from Carboxylic Acids Using Thionyl Chloride in Dimethylacetamide in the Absence of Bases”, Org. Process Res. Dev. 2006, 10, 944.
  10. Chung, J.; Cai, C.; McWilliams, J. C.; Reamer, R.; Dormer, P; Cvetovich, R. J. “Efficient Synthesis of a Trisubstituted 1,6-Naphthyridone from Acetonedicarboxylate and Regioselective Suzuki Arylation”, J. Org. Chem. 2005, 70, 10342-10347.
  11. Klapars, A.; Waldman, J. H.; Campos, K. R.; Jensen, M. S.; McLaughlin, M.; Chung, J.; Cvetovich, R. J.; Chen, C.  “Mild and Practical Method for the a-Arylation of Nitriles with Heteroaryl Halides”, J. Org. Chem. 2005, 70, 10186-10189.
  12. Leazer, J. L. Jr.; Cvetovich, R. “A Practical and Safe Preparation of 3, 5-Bis(trifluoromethyl)­acetophenone”, Org. Synthesis 2005, 82, 115-119.
  13. Cvetovich, R. J.; Chung, J.; Kress, M. H.; Amato, J. S.; Matty, L.; M. Weingarten, D.; Tsay, F.-R.; Li, Z.; Zhou, G. “An Efficient Synthesis of a Dual PPAR a/g Agonist and the Formation of a Sterically Congested a-Aryloxyisobutyric Acid via a Bargellini Reaction”, J. Org. Chem. 2005, 70, 8560-8563.
  14. Chung, J. Y. L.; Cvetovich, R.; Amato, J. S.; McWilliams, J. C.; Reamer, R.; DiMichele, L. “Enantioselective Nitrile Anion Cyclization to Substituted Pyrrolidines. A Highly Efficient Synthesis of (3S,4R)-N-tert-Butyl-4-Arylpyrrolidine-3-Carboxylic Acid”, J. Org. Chem. 2005, 70, 3592-3601.
  15. Amato, J. S.; Chung, J. Y. L.; Cvetovich, R. J.; Gong, X.; McLaughlin, M.; Reamer, R. A.  “Synthesis of 1-tert-Butyl-4-chloropiperidine: Generation of an N-tert-Butyl Group by the Reaction of Dimethyliminium Salt with Methylmagnesium Chloride”,  J. Org. Chem. 2005,  70, 1930-1933.
  16. 16.  Amato, J. S.; Chung, J. Y. L.; Cvetovich, R. J.; Reamer, R.A.; Zhao, D.; Zhou, G.; Gong, X. “Acrylate as an Efficient Dimethylamine Trap for the Practical Synthesis of 1-tert-Butyl-4-peperidone via Transamination”, Org. Process Res. Dev. 2004, 8, 939-941.
  17. Cvetovich, R. J.; Pipik, B.; Hartner, F. W.; Grabowski, E. J. J. “Rapid Synthesis of Tetrahydro-4H-Pyrazolo-[1,5-a]diazepine-2-Carboxylate”, Tetrahedron. Lett. 2003, 44, 5867-5870
  18. Leazer, J. L. Jr.; Cvetovich, R. J.; Tsay, F-R; Dolling, U.; Vickery, T.; Bachert, D. “An Improved Preparation of 3,5-Bis(trifluoromethyl)acetophenone and Safety Considerations in the Preparation of 3,5-Bis(trifluoromethyl)phenyl Grignard Reagent”, J. Org. Chem. 2003, 68, 3695-3698.
  19. Chung, J.Y.L.; Cvetovich, R. J.; Tsay, F-R.; Dormer, P.G.; DiMichele, L.; Mathre, D. J.; Chilenski, J. R.; Mao, B.; Wenslow, R.  “Synthesis of 3-Aminopyrazinone Mediated by 2-Pyridylthioimidate-ZnCl2 Complexes. Development of an Efficient Route to a Thrombin Inhibitor”,  J. Org. Chem. 2003, 68, 8838-8846.
  20. Hartner, F. W.; Cvetovich, R. J.; Tsay, F.-R.; Amato, J. S.; Pipik, B.; Grabowski, E. J. J.; Reider, P. J.  ”A Highly Convergent Synthesis of a Fibrinogen Receptor Antagonist”, J. Org. Chem. 1999, 64, 7751-7755.
  21. Amato, J. S.; Bagner, C.; Cvetovich, R. J.; Gomolka, S.; Hartner, F. W. Jr.; Reamer, R.  “Development of the Hofmann Rearrangement of N-Tosyl Asparagine through Calorimetric and NMR Analysis”, J. Org. Chem. 1998, 63, 9533-9534.
  22. Cvetovich, R. J.; Amato, J. S.; DiMichele, L.; Weinstock, L.; Hazen, G.  “Novel Electrochemical Reductive Amination of 4”-Oxo-5-O-(t-Butyldimethylsilyl)-Avermectin B1”, J. Org. Chem. 1997, 62, 6697-6698.
  23. Cvetovich, R. J.; Senanayake, C. H.; Amato, J. S.; DiMichele, L. M.; Bill, T. J.; Larsen, R. D.; Shuman, R. F.; Verhoeven, T. R.; Grabowski, E. J. J. “Practical Syntheses of 13-O-[(2-methoxyethoxy)methyl]-22,23-Dihydroavermectin B­1 Aglycone[Dimedectin Isopropanol, MK-324] and 13-epi-O-methoxymethyl-22,23-Dihydroavermectin B­1 Aglycone [L-694,554], Flea Active Ivermectin Analogues”, J. Org. Chem. 1997, 62, 3989-3993.
  24. Roberge, C.; Cvetovich, R. J.; Amato, J. S.; Pecore, V.; Hartner, F. W. Jr.; Greasham, R.; Chartrain, M.  “Process Development for the Production of the (S)-Acid Precursor of a Novel Elastase Inhibitor (L-694,458) through the Lipase-Catalyzed Kinetic Resolution of a b-Lactam Benzyl Ester”, J. Fermentation and Bioengineering 1997, 83, 48-53.
  25. Cvetovich, R. J.; Chartrain, M.; Hartner, F. W. Jr.; Roberge, C.; Amato, J. S. “An Asymmetric Synthesis of L-694,458, a Human Leukocyte Elastase (HLE) Inhibitor, via a Novel Enzyme Resolution of β-Lactam Esters”, J. Org. Chem. 1996, 61, 6575-6580.
  26. Cvetovich, R. J.*; Loewe, M. F.; DiMichele, L. M.; Shuman, R. F.; Grabowski, E. J. J.  ”Glycosidation Route to 4″-epi-Methylamine-4″-deoxyavermectin B1 (MK-244, Emamectin Benzoate)”, J. Org. Chem. 1994, 59, 7870-7875.
  27. Cvetovich, R. J.; Kelly, D. H.; DiMichele, L. M.; Shuman, R. F.; Grabowski, E. J. J.  ”Synthesis of 4″-epi-Amine-4″-deoxyavermectins”, J. Org. Chem. 1994, 59, 7704-7708.
  28. Cvetovich, R. J.*; Leonard, W. R.; Amato, J.S.; DiMichele, L.M.; Reamer, R.A.; Shuman, R.F.; Grabowski, E. J. J. “Oxime Formation of 4″-epi-Acetylamino-5-oxo-4″-deoxyavermectin B1″, J. Org. Chem. 1994, 59, 5838-5840.
  29. Loewe, M. F.; Cvetovich, R. J.; Hazen, G. “An Efficient b-Amino Acid Cyclodehydration using Methanesulfonyl Chloride to Thienamycin Intermediate 3-[1-Hydroxyethyl]-4-[methoxycarbonylmethyl]-azetidine-2-one”, Tetrahedron Lett. 1991, 32, 2299-2302.
  30. Natsugari, H.; Turos, E.; Weinreb, S. M.; Cvetovich, R. J. “Further studies on Stereoselective Synthesis of Vicinal Diamines from 3,6-Dihydrothiazine-1-imines”, Heterocycles 1987, 25, 19-24.
  31. Melillo, D. G.*; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. “An Enantioselective Approach to (+)-Thienamycin from Dimethyl 1,3-Acetone Dicarboxylate and (+)-a-Methylbenzylamine”, J. Org. Chem. 1986, 51, 1498-1504.
  32. Danishefsky, S.; Berman, E.; Cvetovich, R.; Minamikawa, J. “The Total Synthesis of Renierone”, Tetrahedron Lett. 1980, 21, 4819-4822.
  33. Weinreb, S. M.; Cvetovich, R. J. “A Synthesis of cis-Jasmone”, Tetrahedron Lett. 1972, 1233-123

PATENTS

  1. “Nucleosidic Phosphoramidite Crystalline Material and a Process for Purifying the Same”, WO 2010/021897 A1, 25 February 2010 International Publication Date, PCT/US2009/053640
  2. “Crystalline forms of carbapenem antibiotics and methods of preparation”, US 7,145,002, 05 December 2006.
  3. “Process for making Carbapenam Compounds”,US 7,022,841, 04 April, 2006.
  4. “Process for the Synthesis of 1(3,5-Bis (trifluoromethyl) phenyl) ethan-1-one”, US 6,814,895, 09 November 2004.
  5. “Process for the Synthesis of 3, 5-Bis (trifluoromethyl) Benzoic Acid”,US 6,489,507, 03 December 2002.
  6. “Thermodynamically Stable Crystal Form of 4-Deoxy-4-epi-Methyl­amino ­Avermectin B1a/B1b Benzoic Acid Salt and Processes for its     Preparation”,US 6,486,195 ,26 November 2002.
  7. “Process for the Synthesis of 1-(3,5-Bis (trifluoromethyl)-phenyl) ethan-1-one”,US 6,350,915, 26 February 2002.
  8. “Process for the Synthesis of 3,5-Bis (trifluoromethyl) bromobenzene”,US 6,255,545, 03 July 2001.
  9. “Process for the Preparation of Substituted Azetidinones”,US 5,808,056, 15 September 1998.
  10. “Stable solvates of MK324”, EP 949313107.6-1219, 07 June 1996.
  11. “Enzymatic Hydrolysis of 3.3-Diethyl-4-[(4-carboxy) phenoxy]-2-Azetidinone esters”,US 5,523,233, 04 June 1996.
  12. “Process for L-685,869”,US 5,420,260, 30 May 1995.
  13. “Glycosidation route to MK-244”,US 5,399,717, 21 March 1995.
  14. “Stable Solvate of MK-324”,US 5,380,838, 10 January 1995.
  15. ”Process for 4″-aminoavermectin”, US 5,362,863, 08 November 1994.
  16. “Process for L-685,869”,US 5,362,862, 08 November 1994.
  17. “Stable salts of 4″-deoxy-4″-epi-methylamino avermectin B1a/B1b”,US 5,288,710, 22 February 1994.
  18. “Cyclization Process for Synthesis of a Beta-Lactam Carbapenem Intermediate”, US 5,037,974, 06 August 1991.
  19. “Process for Synthesis of a Beta-Lactam Carbapenem Intermediate”, European Patent 89 201238.6, 09 June 1989.
  20. “Process for the Preparation of (2S)-Tetrahydro-2a-methyl-6-oxo-4b-amino-2H-pyran-3a-carboxylic Acid”,US 4,360,684, 23 November 1982.