Chemistry Publications by David Askin

David Askin has published nearly 50 peer-reviewed publications on process chemistry and biotech/pharmaceutical drug development.

  1. Tian, Q.; Hoffmann, U.; Humphries, T.; Cheng, K.; Hidber, P.; Yajima, H.; Guillemot-Plass, M.; Li, J.; Bromberger, U.; Babu, S.; Askin, D.; Gosselin, F.; “A Practical, Protecting Group Free Synthesis of a PI3K/mTOR Inhibitor” Organic Process Research & Development 2015, 19, 416-426.
  2. Remarchuk, T.; St-Jean, F.; Carrera, D.; Savage, S.; Yajima, H.; Wong, B.; Babu, S.; Deese, A.; Stults, J.; Dong, M.; Askin, D.; Lane, J.; Spencer, K.; “Synthesis of Akt Inhibitor Ipatasertib. Part 2. Total Synthesis and First Kilogram Scale-up” Organic Process Research & Development 2014, 18, 1652-1666.
  3. Tian, Q.T.; Cheng, Z.; Yajima, H.M. ; Savage, S.J.; Green, K.L.; Humphries, T.; Reynolds, M.E.; Babu, S.; Gosselin, F.; Askin, D.; Kurimoto, I.; Hirata, N.; Iwasaki, M.; Shimasaki, Y.; Miki, T.; “A Practical Synthesis of a PI3K Inhibitor under Noncryogenic Conditions via Functionalization of a Lithium Triarylmagnesiate Intermediate” Organic Process Research & Development 2013, 17, 97-107.
  4. Zhong, Yong-Li; Boruta, D. T.; Gauthier, D. R.; Askin, D. “An Efficient Synthesis of 4-Chromanones”, Tetrahedron Letters 2011, 52, 4824-4826.
  5. Humphrey, G.R.; Pye, P.J.; Zhong,Y-L; Angelaud, R.; Askin, D.; Belyk, K. M.; Maligres, P. E.; Mancheno, D.; Miller, R. A.; Reamer, R. A.; Weissman, S.; “Development of a Second-Generation, Highly Efficient Manufacturing Route for the HIV Integrase Inhibitor Raltegravir Potassium” Organic Process Research & Development 2011, 15, 73-83.
  6. Zhong, Y.-L.; Krska, S.W.; Zhou, H.; Reamer, R.A.; Lee, J.; Sun, Y.; Askin, D. “Catalytic Asymmetric Synthesis of an HIV Integrase Inhibitor” Lett., 2009, 11, 369-372.
  7. Zhong, Y.-L.; Pipik, B.; J. Lee; Kohmura, Y.; Okada, S.; Igawa, K.; Kadowaki, C.; Takezawa, A.; Kato, S.; Conlon, D.; Zhou, H.; King, A. O.; Reamer, R. A.; Gauthier, D. R., Jr.; Askin, D. “Practical Synthesis of an HIV Integrase Inhibitor” Process Res. Dev. 2008, 12, 1245-1252.
  8. Pye, P.; Zhong, Y-L; Jones, G.; Reamer, R.; Houk, K.; Askin, D. “A Polar Radical Pair Pathway to Assemble the Pyrimidinone Core of the HIV Integrase Inhibitor Raltegravir Potassium” Chem. Int. Ed. 2008, 47/22, 4134-4136.
  9. Zhong, Yong-Li; Zhou, Hua; Gauthier, Donald R. Jr.; Askin, David “Efficient Synthesis of Functionalized Pyrimidones via Microwave-Accelerated Rearrangement Reaction” Tetrahedron Letters 2006, 47, 1315-1317.
  10. Hansen, K. B.; Balsells, J.; Dreher, S.; Hsiao, Y.; Kubryk, M.; Palucki, M.; Rivera, N.; Steinhuebel, D.; Armstrong, J.D.; Askin, D.; Grabowski, E. J. J. “First Generation Process for the Preparation of the DPP-IV Inhibitor Sitagliptin” Organic Process Research & Development 2005, 9, 634-639.
  11. Angelaud, R.; Zhong, Y.L.; Maligres, P.; Lee, J.; Askin, D. “Synthesis of a b-Amino Acid Pharmacophore via a b-Lactam Intermediate” Org. Chem. 2005, 70, 1949-1952.
  12. Zhong, Y.-L.; Zhou, H.; Gauthier, D. R. Jr.; Lee, J.; Askin, D.; Dolling, U. H., Volante, R. P., Practical and Efficient Synthesis of N-Halo Compounds, Tetrahedron Lett., 2005, 46, 1099-1101.
  13. D. Steinhuebel, M. Palucki, D. Askin and U. Dolling, “Synthesis of N-arylated Sultams: Palladium- and Copper-catalyzed Cross Coupling of Aryl Halides with 1,4-Butane and 1,3-Propanesultams” Tetrahedron Lett 2004, 45, 3305-3307.
  14. K. Belyk, C. Beguin, M. Palucki, N. Grinberg, J. DaSilva, D. Askin and N. Yasuda, “A Rapid Catalytic asymmetric Synthesis of 1,3,4-Trisubstituted Pyrrolidines” Tetrahedron Lett. 2004, 45, 3265-3268.
  15. Y.-L. Zhong, J. Lee, R. Reamer and D. Askin, “New Method for the Synthesis of Diversely Functionalized Imidazoles from N-Acylated -Aminonitriles” Org. Lett. 2004, 6, 929-931.
  16. J. Lee, Y-L. Zhong, R. Reamer and D. Askin, “Practical Synthesis of Sultams via Sulfonamide Dianion Alkylation: Application to the Synthesis of Chiral Sultams” Org. Lett. 2003, 5, 4175-4177.
  17. P. Maligres, M. Waters, S. Weissman, C. McWilliams, R. Reamer, S. Volante, P. Reider, D. Askin, “Preparation of a Clinically Investigated Ras Farnesyl Transferase Inhibitor” Journal of Heterocyclic Chem. 2003, 40, 229-241.
  18. P. Maligres, M. Waters, J. Lee, R. Reamer, D. Askin, M. Ashwood, M. Cameron, “Stereocontrolled Preparation of a Nonpeptidal (-)-Spirobicyclic NK-1 Receptor Antagonist, J. Org. Chem. 2002, 67, 1093-1101.
  19. J. Lee, T. Hoang, S. Lewis, S. Weissman, D. Askin, R. Volante, P. Reider “Asymmetric Synthesis of (2S,3S)-3-Hydroxy-2-PhenylPiperidine via Ring Expansion”, Tetrahedron Lett, 2001, 42, 6223-6225.
  20. M.S. Waters, J. A. Cowen, J. C. McWilliams, P.E. Maligres and D. Askin, “Thiol Addition to Aryl Propargyl Alcohols Under Mild Conditions: an Accelerating Neighboring Group Effect”, Tetrahedron Lett. 2000, 41, 141-144.
  21. P. Maligres, M. Waters, F. Fleitz and D. Askin, “A Highly Catalytic Robust Palladium Catalyzed Cyanation of Aryl Bromides”, Tetrahedron Lett. 1999, 40, 8193-8195.
  22. M. Chartrain, P. Maligres, D. Cohen, V. Upadhyay, V. Pecore, D. Askin, R. Greasham, “Porcine Liver Esterase-Catalyzed Enantioselective Hydrolysis of a Prochiral Diester into Its Optically Pure (S)-Ester Acid, a Precursor to a Growth Hormone Secretagogue”, J. Bioscience and Bioengineering 1999, 87, 386-389.
  23. P.E. Maligres, M. M. Chartrain, V. Upadhyay, D. Cohen, R.R. Reamer, D. Askin, R.P. Volante, P.J. Reider, “Preparation of (S)-3-Carbethoxy-3-benzylpiperidine and the Growth Hormone Secretagogue L-163,540”, J. Org. Chem. 1998, 63, 9548-9551.
  24. D. Askin, “The Synthesis of Indinavir and Other Clinically Useful HIV-1 Protease Inhibitors”, Current Opinion in Drug Discovery & Development 1998 1, 338-348.
  25. S.A. Weissman, S. Lewis, D. Askin, R.P. Volante, P.J. Reider,Efficient Synthesis of N-Arylpiperazinones via a Selective Intramolecular Mitsunobu Cyclodehydration”, Tetrahedron Lett. 1998, 39, 7459-7462.
  26. R. Scott Hoerrner, David Askin, R. P. Volante and Paul J. Reider, “Highly Enantioselective Asymmetric Hydrogenation Route to ß-(2R,3S)-Methyltryptophan”, Tetrahedron Lett. 1998, 39, 3455-3458.
  27. P.E. Maligres, M.M. See, D. Askin and P.J. Reider, “Nosylaziridines, Activated Aziridine Electrophiles”, Tetrahedron Lett. 1997, 38, 5253-5256.
  28. P.E. Maligres, I. Houpis, K. Rossen, A. Molina, J. Sager, V. Upadhyay, K.M. Wells, R.A. Reamer, J.E. Lynch, D. Askin, R. P. Volante, P.J. Reider and P. Houghton, “Synthesis of the Orally Active Nonpeptidal Growth Hormone Secretagogue, MK-677, Tetrahedron, 1997, 10983-10992.
  29. P.E. Maligres, S.A. Weissman, V. Upadhyay, S.J. Cianciosi, R.A. Reamer, R.M. Purick, J. Sager, K. Rossen, K.K. Eng, D. Askin, R.P. Volante and P.J. Reider, “Cyclic Imidate Salts in Acyclic Stereochemistry: Diastereoselective Syn-Epoxidation of 2-Alkyl-4-Enamides to Epoxyamides, Tetrahedron, 1996, 52, 3327-3338.
  30. K. Rossen, S.A. Weissman, J. Sager, R.A. Reamer, D. Askin, R.P. Volante and P.J. Reider, “Asymmetric Hydrogenation of Tetrahydropyrazines: Synthesis of (S)-Piperazine-2-tert-butylcarboxamide, an Intermediate in the Preparation of the HIV Protease Inhibitor Indinavir”, Tetrahedron Letters, 1995, 36, 6419-6422.
  31. K. M. Wells, K. Rossen, D. Askin, F. Hartner, R. P. Volante and P. J. Reider, “Michael Additions of 3,3-Dimethylacrylamides and Amines: Synthesis of the Growth Hormone Secretagogue L-692,585”, Synthetic Communications, 1995, 25, 219.
  32. P.E. Maligres, V. Upadhyay, K. Rossen, S.J. Cianciosi, R.M. Purick, K.K. Eng, R.A. Reamer, D.Askin, R.P. Volante and P.J. Reider, “Diastereoselective Syn-Epoxidation of 2-Alkyl-4-Enamides to Epoxyamides: Synthesis of the Merck HIV-1 Protease Inhibitor Epoxide Intermediate”, Tetrahedron Letters 1995, 36, 2195-2198.
  33. J.D Armstrong, K.K. Eng, J.L. Keller, R.M. Purick, F.W. Hartner, W.-B. Choi, D. Askin, and R.P. Volante, “An Efficient Asymmetric Synthesis of (R)-3-Amino-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one”, Tetrahedron Letters 1994, 35, 3239-3242.
  34. D. Askin, K.K. Eng, K. Rossen, R.M. Purick, K.M. Wells, R.P. Volante, and P. J. Reider, “Highly Diastereoselective Reaction of a Chiral, Non-Racemic Amide Enolate with (S)-Glycidyl Tosylate. Synthesis of the Orally Active HIV-1 Protease Inhibitor L-735,524”, Tetrahedron Letters 1994, 35, 673-676.
  35. D. Askin, M.A. Wallace, J.P. Vacca, R.A. Reamer, R.P. Volante and I. Shinkai, “Highly Diastereoselective Alkylations of Chiral Amide Enolates: New Routes to Hydroxyethylene Dipeptide Isostere Inhibitors of HIV-1 Protease”, Journal of Organic Chemistry, 1992, 57, 2771-2773.
  36. D. Askin, T.R. Verhoeven, T.M.-H. Liu and I. Shinkai, “Synthesis of Synvinolin: Extremely High Conversion Alkylation of an Ester Enolate”, Journal of Organic Chemistry, 1991, 56, 4929.
  37. D. Askin, D. Joe, R. A. Reamer, R. P. Volante and I. Shinkai, “Efficient Degradation of FK-506 to a Versatile Synthetic Intermediate”, Journal of Organic Chemistry, 1990, 55, 5451.
  38. D. Askin, R.A. Reamer, D. Joe, R.P. Volante and I. Shinkai, “Synthesis of the Novel Sarcosine and Proline (FK-525) Analogues of FK-506: Rearrangement of the Allylic Ester System”, Journal of Organic Chemistry, 1990, 55, 5448.
  39. D. Askin, R. A. Reamer, D. Joe, R.P. Volante and I. Shinkai, “A Mechanistic Study of the FK-506 Tricarbonyl System Rearrangement: Synthesis of C9 Labeled FK-506”, Tetrahedron Letters 1989, 30, 6121.
  40. T. K. Jones, S. G. Mills, R. A. Reamer, D. Askin, R. Desmond, R. P. Volante and I. Shinkai, “Total Synthesis of the Immunosuppressant (-)-FK-506”, Journal of the American Chemical Society 1989, 111, 1157.
  41. D. Askin, R.A. Reamer, T.K. Jones, R.P. Volante and I. Shinkai, “Chemistry of FK-506: Benzilic Acid Rearrangement of the Tricarbonyl System”, Tetrahedron Letters 1989, 30, 671.
  42. D. Askin, R.P. Volante, K.M. Ryan, R.A. Reamer and I. Shinkai, “Alkylation of Chiral Prolinol Propionamide Enolates with Epoxides: Complete Reversal of Predicted Facial Selectivity”, Tetrahedron Letters 1988, 29, 4245.
  43. D. Askin, R.P. Volante, R.A. Reamer, K.M. Ryan and I. Shinkai, “A Diastereospecific, Non-Racemic Synthesis of the C10-C18 Segment of FK-506”, Tetrahedron Letters 1988, 29, 277.
  44. D. Askin, C. Angst and S. Danishefsky, “An Approach to the Synthesis of Bactobolin and the Total Synthesis of N-Acetylactinobolamine: Some Remarkably Stable Hemiacetals”, Journal of Organic Chemistry 1987, 52, 622.
  45. D. Askin, C. Angst and S. Danishefsky, “A Total Synthesis of N-Acetyl-actinobolamine”, Journal of Organic Chemistry 1985, 50, 5005.
  46. S. Danishefsky, E. Larson, D. Askin and N. Kato, “On the Scope, Mechanism, and Stereochemistry of the Lewis Acid Catalyzed Cyclocondensation of Activated Dienes with Aldehydes: An Application to the Erythronolide Problem”, Journal of the American Chemical Society 1985, 107, 1246.
  47. S. Danishefsky, E. R. Larson and D. Askin, “Stereochemical Variations in the Cyclocondensation of Aldehydes with Siloxydienes. An Application to the Erythronolide Series”, Journal of the American Chemical Society 1982, 104, 6457.
  48. S. Danishefsky, N. Kato, D. Askin and J.F. Kerwin, Jr., “Stereochemical Consequences of the Lewis Acid Catalyzed Cyclocondensation of Oxygenated Dienes with Aldehydes. A Rapid and Stereoselective Entry to the Various Natural Products Derived From Propionate”, Journal of the American Chemical Society 1982, 104, 360.