The KCN Chemistry Group

Publications & Patents

1. Diastereomeric Monocyclic Diallenes. The Synthesis of Cyclododeca-3,4,9,10-tetraene-1,7-dione, K.C. Nicolaou, P.J. Garratt, F. Sondheimer, J. Chem. Soc., Chem. Commun. 1970, 1219–1220.

2. Synthesis of Cyclotetradeca-3,4,5,10,11,12-hexaene-1,8-dione, a Monocyclic Dicumulenedione, K.C. Nicolaou, P.J. Garratt, F. Sondheimer, J. Chem. Soc., Chem. Commun. 1971, 1018–1019.

3. Diastereomeric Monocyclic Diallenes. The Stereochemistry of Formation of Racemic and Meso-3,4,9,10-Cyclododecatetraene-1,7-dione, K.C. Nicolaou, P.J. Garratt, F. Sondheimer, Tetrahedron Lett. 1972, 3425–3428.

4. Diastereomeric Monocyclic Diallenes. The Synthesis and Properties of the Diastereomeric 3,4,9,10-Cyclodecatetraene-1,7-diones and 3,4,10,11-Cyclotetradecatetraene-1,8-diones, K.C. Nicolaou, P.J. Garratt, F. Sondheimer, J. Am. Chem. Soc. 1973, 95, 4582–4592.

5. Monocyclic Allenes. The Synthesis of 3,8,9-Cycloundecatriene-1,6-dione and 12-Oxabicyclo[7.2.1]dodeca-5,6,9,11-tetraene-3-one, a Furanophane Containing an Allene Group, K.C. Nicolaou, P.J. Garratt, F. Sondheimer, J. Org. Chem. 1973, 38, 864–868.

6. The Synthesis of 3,4,5,10,11,12-Cyclotetradecahexaene-1,8-dione, a Monocyclic Dicumulene dione, K.C. Nicolaou, P.J. Garratt, F. Sondheimer, J. Org. Chem. 1973, 38, 2715–2717.

7. Additions of Chlorosulfonyl Isocyanate and Sulfenyl Halides to Benzvalene, K.C. Nicolaou, Thomas J. Katz, J. Am. Chem. Soc. 1974, 96, 1948–1949.

8. A Short Synthetic Route to Prostaglandins Utilizing Position-Selective Epoxide Opening by the Vinyl Gilman Reagent, E.J. Corey, K.C. Nicolaou, D.J. Beames, Tetrahedron Lett. 1974, 2439–2440.

9. An Efficient and Mild Lactonization Method for the Synthesis of Macrolides, E.J. Corey, K.C. Nicolaou, J. Am. Chem. Soc. 1974, 96, 5614–5616.

10. Synthesis of Novel Macrocyclic Lactones in the Prostaglandin and Polyether Antibiotic Series, E.J. Corey, K.C. Nicolaou, L.S. Melvin, J. Am. Chem. Soc. 1975, 97, 653–654.

11. Synthesis of Brefeldin A, Carpaine, Vertaline, and Erythronolide B from Non-Macro-cyclic Precursors, E.J. Corey, K.C. Nicolaou, L.S. Melvin, J. Am. Chem. Soc. 1975, 97, 654–655.

12. Total Synthesis of (±)-Vermiculine, E.J. Corey, K.C. Nicolaou, T. Toru, J. Am. Chem. Soc. 1975, 97, 2287.

13. Superoxide Ion as a Synthetically Useful Oxygen Nucleophile, E.J. Corey, K.C. Nicolaou, M. Shibasaki, Y. Machida, C.S. Shiner, Tetrahedron Lett. 1975, 3183–3186.

14. A Useful Method for the Conversion of Azides to Amines, E.J. Corey, K.C. Nicolaou, M. Shibasaki, Y. Machida, C.S. Shiner, Synthesis 1975, 590–591.

15. Synthesis and Biological Properties of a 9,11-Azo-Prostanoid. A Highly Active Biochemical Mimic of Prostaglandin Endoperoxides. E.J. Corey, K.C. Nicolaou, Y. Machida, C.L. Malmsten, B. Samuelsson, Proc. Natl. Acad. Sci. USA 1975, 72, 3355–3358.

16. Simple Stereospecific Routes to 9-epi-Prostaglandin F₂ (PGF₂) and 11-epi-Prostaglandin F2, E.J. Corey, K.C. Nicolaou, M. Shibasaki, J. Chem. Soc., Chem. Commun. 1975, 658–659.

17. A Simple, Stereocontrolled Total Synthesis of a Biologically Active Analog of Prostaglandin Endoperoxides (PGH₂, PGG₂), E.J. Corey, M. Shibasaki, K.C. Nicolaou, C.L. Malmsten, B. Samuelsson, Tetrahedron Lett. 1976, 737–740.

18. Stimulation of Renin Release from Rabbit Renal Cortex by Arachidonic Acid and Prostaglandin Endoperoxides, P.C. Weber, C. Larsson, E. Anggard, M. Hamberg, E.J. Corey, K.C. Nicolaou, B. Samuelsson, Circulation Res. 1976, 39, 868–874.

19. A Translactonization Route to Macrocyclic Lactones, E.J. Corey, D.J. Brunelle, K.C. Nicolaou, J. Am. Chem. Soc. 1977, 99, 7359–7360.

20. Synthesis of Macrolides, K.C. Nicolaou, Tetrahedron 1977, 33, 683.

21. Phenylselenolactonization. An Extremely Mild and Synthetically Useful Cyclization Process, K.C. Nicolaou, Zenon Lysenko, J. Am. Chem. Soc. 1977, 99, 3185–3187.

22. Phenylsulfenylactonization: An Easy and Synthetically Useful Lactonization Procedure, K.C. Nicolaou, Zenon Lysenko, J. Chem. Soc., Chem. Commun. 1977,293–294.

23. The Use of PhSeCl in the Synthesis of Cyclic Ethers, K.C. Nicolaou, Zenon Lysenko, Tetrahedron Lett. 1977,1257–1260.

24. Synthesis of (4E)-Deoxy-6,9-Epoxy-4-PGF1, a Prostacyclin (PGX) Isomer, K.C. Nicolaou, W.E. Barnette, J. Chem. Soc., Chem. Commun. 1977, 331–332.

25. Simple Efficient Synthesis of Prostacyclin (PGI₂), K.C. Nicolaou, W.E. Barnette, G.P. Gasic, R.L. Magolda, W.J. Sipio, J. Chem. Soc., Chem. Commun. 1977, 630–631.

26. 6,9-Thiaprostacyclin. A Stable and Potent Biological Analog of Prostacyclin (PGI₂), K.C. Nicolaou, W.E. Barnette, G.P. Gasic, R.L. Magolda, J. Am. Chem. Soc. 1977, 99, 7736–7738.

27. Total Synthesis of Erythromycins (Part III). Stereoselective Routes to Intermediates Corresponding to C(1) to C(9) and C(10) to C(13) Fragments of Erythronolide B, E.J. Corey, E.J. Trybulski, L.J. Melvin, Jr., K.C. Nicolaou, J.A. Secrist, R. Lett, P.W. Sheldrake, J.R. Falck, D.J. Brunelle, M.F. Haslanger, S. Kim, S. Yoo, J. Am. Chem. Soc. 1978, 100, 4618–4620.

28. Total Synthesis of Erythromycins (Part IV). Total Synthesis of Erythromolide B, E.J. Corey, S. Kim, S. Yoo, K.C. Nicolaou, L.J. Melvin, Jr., D.J. Brunelle, J.R. Falck, E.J. Trybulski, R. Lett, P. W. Sheldrake, J. Am. Chem. Soc. 1978, 100, 4620–4622.

29. Synthesis and Biological Properties of Prostaglandin Endoperoxides, Thromboxanes and Prostacyclins, K.C. Nicolaou, G.P. Gasic, W.E. Barnette, Angew. Chem. Int. Ed. Engl. 1978, 17, 293–312.

30. Organoselenium-Induced Ring Closures. Sulfur-Containing Prostacyclins. Stereoselctive Synthesis of Cyclic, α, β-Unsaturated Sulfoxides, Sulfones and Sulfides and Synthesis of 6,9-Sulfoxa-5(E)-and 5(Z)-Prostacyclin, and 6,9-Sulfo-5(E)- and 5(Z)-Prostacyclin, 6,9-Sulfo-6a- and 6b-4(E)-Isoprostacyclin and 6,9-Thiaprostacyclin, K.C. Nicolaou, W.E. Barnette, R.L. Magolda, J. Am. Chem. Soc. 1978, 100, 2567–2570.

31. Synthesis of Sulfur-Containing Prostacyclin PGI₁ Analogues. 6,9-Epithio-PGI1, its S-Oxide Stereoisomers and its SS-Dioxide, K.C. Nicolaou, R.L. Magolda, W.E. Barnette, J. Chem. Soc., Chem. Commun. 1978, 375–377.

32. Total Synthesis of 14-Fluoroprostaglandin F_2a and 14-Fluoroprostacyclin, P.A. Grieco, Y. Yokoyama, K.C. Nicolaou, W.E. Barnette, J.B. Smith, M. Ogletree, A.M. Lefer, Chemistry Lett. 1978, 1001–1004.

33. Synthesis and Biological Properties of 12-Fluoroprostacyclin, K.C. Nicolaou, W.E. Barnette, R.L. Magolda, P.A. Grieco, W. Owens, C.-L. J. Wang, J.B. Smith, M. Ogletree, A.M. Lefer, Prostaglandins 1978, 16, 789–794.

34. Synthesis of Prostaglandin H₂ (PGH₂) and Prostacyclin (PGI₂) Analogs: Tetrathia-PGH₂ and PGI₂-Ketal Methyl Ester, K.C. Nicolaou, W.E. Barnette, R.L. Magolda, Prostaglandins and Medicine 1978, 1, 96–97.

35. Total Synthesis of Carboprostacyclin, a Stable and Biologically Active Analog of Prostacyclin (PGI₂), K.C. Nicolaou, W.J. Sipio, R.L. Magolda, S. Seitz, W.E. Barnette, J. Chem. Soc., Chem. Commun. 1978, 1067–1068.

36. Prostacyclin: A Potentially Valuable Agent for Preserving Myocardial Tissue in Acute Myocardial Ischemia, A.M. Lefer, M.L. Ogletree, J.B. Smith, M.J. Silver, G.P. Gasic, W.E. Barnette, K.C. Nicolaou, Science 1978, 200, 52–54.

37. Prostaglandin I₂ as a Potentiator of Acute Inflammation in Rats, K. Komoriya, J. Ohmori, A. Azuma, S. Kurozumi, Y. Hashimoto, K.C. Nicolaou, W.E. Barnette, R.L. Magolda, Prostaglandins 1978, 15, 557–564.

38. Cardiac and Renal Prostaglandin I₂: Biosynthesis and Biological Effects in Isolated Perfused Rabbit Tissues, P. Needleman, S.D. Bronson, A. Wyche, K.C. Nicolaou, M. Sivakoff, J. Clin. Invest. 1978, 61, 839–849.

39. Effects of Prostacyclin on Perfusion Pressure, Electrical Activity Rate and Force of Contraction in Isolated Rat and Rabbit Hearts, M. Karmazyn, D.F. Horrobin, M.S. Manku, S.C. Cunnane, R.A. Karmali, A.I. Ally, R.O. Morgan, K.C. Nicolaou, Life Sciences 1978, 22, 2079–2086.

40. Antibodies which Antagonize the Effects of Prostacyclin, J.B. Smith, M. Ogletree, A.M. Lefer, K.C. Nicolaou, Nature 1978, 274, 64–65.

41. Prostaglandins E₁, E₂ and I₂: Evidence for Three District Actions in Vascular Smooth Muscle, M.S. Manku, D.F. Horrobin, S.C. Cunnane, A.I. Ally, M. Karmazyn, R.A. Karmali, R.O. Morgan, K.C. Nicolaou, W.E. Barnette, Biochem. Biophys. Res. Commun. 1978, 83, 295–299.

42. Prostaglandin I₂ Has More Potent Hypotensive Properties than Prostaglandin E₂ in the Normal Spontaneously Hypertensive Rat, C.R. Pace-Asciak, M.C. Carrera, K.C. Nicolaou, Prostaglandins 1978, 15, 999–1003.

44. A Triple Test for Screening Biological Activity of Prostacyclin Analogs, R.J. Gryglewski, K.C. Nicolaou, Experientia 1978, 34, 1336–1338.

45. Studies of the Mechanism Involved in the Fate of Prostacyclin (PGI₂) and 6-Keto-PGF_2a in the Pulmonary Circulation, H.J. Hawkins, J.B. Smith, K.C. Nicolaou, T.E. Eling, Prostaglandins 1978, 16, 871.

46. Synthesis and Chemistry of Prostacyclin (PGI₂), K.C. Nicolaou, W.E. Barnette, R.L. Magolda, J. Chem. Res. (M) 1979, 2437–2445.

47. Synthesis and Biological Properties of Prostacyclins and Prostaglandin Endoperoxide Analogs, K.C. Nicolaou, W.E. Barnette, R.L. Magolda, in Chemistry, Biochemistry and Pharmacological Properties of Prostanoids, S.M. Roberts and F. Scheinmann, Eds., Pergamon Press, New York, 1979, pp. 286–315.

48. 6,9-Pyridazaprostacyclin and Derivatives. The First “Aromatic” Prostacyclins, K.C. Nicolaou, R.L. Magolda, W.E. Barnette, J. Am. Chem. Soc. 1979, 101, 766–768.

49. Reversal of the Phenylseleno- and Phenylsulpheno-cyclizations. Synthesis of Olefins from Phenylseleno-lactones, Phenylseleno-ethers and α-Hydroxyselenides, K.C. Nicolaou, W.J. Sipio, D.A. Claremon, R.L. Magolda, J. Chem. Soc., Chem. Commun. 1979, 83–85.

50. Reaction of Phenylselenenyl Chloride with Enol Ethers and 1,2-Ethanediol Acetals. Synthesis of α-Phenylseleno-aldehydes and α-Phenylseleno-acetals, K.C. Nicolaou, R.L. Magolda, W.J. Sipio, Synthesis 1979, 982–984.

51. Phenylseleno- and Phenylsulfenolactonizations. Two, Highly Efficient and Synthetically Useful Cyclization Procedures, K.C. Nicolaou, S. Seitz, W.J. Sipio, J.F. Blount, J. Am. Chem. Soc. 1979, 101, 3884–3893.

52. Organoselenium-Induced Ring Closures. Cyclization of Dienes with “PhSeOH” to form Cyclic Ethers, R.M. Scarborough, Jr., A.B. Smith, III, W.E. Barnette, K.C. Nicolaou, J. Org. Chem. 1979, 44, 1742–1744.

53. N-Phenylselenophthalimide (N-PSP) and N-Phenylselenosuccinimide (N-PSS). Two Versatile Carriers of the Phenylseleno Group. Oxyselenation of Olefins and a Selenium-Based Macrolide Synthesis, K.C. Nicolaou, D.A. Claremon, W.E. Barnette, S.P. Seitz, J. Am. Chem. Soc. 1979, 101, 3704–3706.

54. Synthesis and Biological Properties of Pinane-Thromboxane A₂ (PTA₂). A Selective Inhibitor of Coronary Artery Constriction, Platelet Aggregation and Thromboxane Formation, K.C. Nicolaou, R.L. Magolda, J.B. Smith, D. Aharony, E.F. Smith, A.M. Lefer, Proc. Natl. Acad. Sci. USA 1979, 76, 2566–2570.

55. Synthesis of 16-Membered Ring Macrolide Antibiotics I. Stereoselective Construction of the “Right Wing” of the Carbomycins and Leucomycins from D-Glucose, K.C. Nicolaou, M.R. Pavia, S.P. Seitz, Tetrahedron Lett. 1979,2327–2330.

56. Synthesis of Macrocycles by Intramolecular Ketophosphonate Reactions. Stereoselective Construction of the “Left Wing” of Carbomycin B and a Synthesis of dl-Muscone from Oleic Acid, K.C. Nicolaou, S.P. Seitz, M.R. Pavia, N. Petasis, J. Org. Chem. 1979, 44, 4011–4013.

57. Total Synthesis of Oestra-1,3,5(10)-trien-17-one, K.C. Nicolaou, W.E. Barnette, J. Chem. Soc., Chem. Commun. 1979,1119–1120.

58. Studies on the Protective Effect of Prostacyclin on Acute Myocardial Ischemia, M.L. Ogletree, A.M. Lefer, J.B. Smith, K.C. Nicolaou, Europ. J. Pharmacol. 1979, 56, 95–103.

59. Effect of 6,9-Thia Prostacyclin I₂ (A Stable PGI₂ Analogue) on Passive Cutaneous Anaphylaxis (PCA) in Rats, K. Komoriya, H. Ohmori, A. Azuma, S. Kurozumi, Y. Hashimoto, K.C. Nicolaou, Japan J. Pharmacol. 1979, 29, 811–813.

60. Prostacyclin, Thromboxanes and The Arachidonic Acid Cascade, K.C. Nicolaou, J.B. Smith, Annual Reports in Medicinal Chemistry, Academic Press, New York, Vol. 14, Ch. 17, 1979, pp. 178–180.

61. Selective Binding Site for 3H-Prostaglandin I₂ on Platelets, A.M. Single, J.B. Smith, M.J. Silver, K.C. Nicolaou, D. Ahern, J. Clin. Invest. 1979, 63, 215–220.

62. Prostaglandin Synthesis by Fetal Rat Bone In Vitro: Evidence for a Role of Prostacyclin, L.G. Raisz, J.Y. Vanderhoek, H.A. Simmons, B.E. Kream, K.C. Nicolaou, Prostaglandins 1979, 17, 905–914.

63. Effects of PGI₂ on Platelet Aggregation Induced by Various Stimulants, A. Ohtsu, K. Hoshina, S. Kurozumi, Y. Hashimoto, T. Noguchi, K.C. Nicolaou, Acta. Haem. Jap. 1979, 42, 659–666.

64. Effects of Prostactyclin and Albumin on Platelet Loss During In Vitro Simulation of Extracorporeal Circulation, V.P. Addonizio, Jr., E.J. Macarak, K.C. Nicolaou, L.H. Edmunds, R.W. Colman, Blood 1979, 53, 1033–1042.

65. Protective Effects of a Novel Thromboxane Analog in Lethal Traumatic Shock, A.M. Lefer, H. Araki, J.B. Smith, K.C. Nicolaou, R.L. Magolda, Prostaglandins and Medicine 1979, 3, 139–146.

66. Circulatory and Platelet Actions of 6,9-Thiaprostacyclin in the Cat, A.M. Lefer, G.J. Trachte, J.B. Smith, W.E. Barnette, K.C. Nicolaou, Life Sciences 1979, 25, 259–264.

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