Do Kyu Pyun, Bong Jin Kim, Hee Jung Jung, Jae Hak Kim, Jin Soo Lee, Won Koo Lee, and Cheol Hae Lee                  

 

5-Methyl-4-hydroxypyrrolidinones (5a—d) were synthesized from the enantiomerically pure aziridine ester (2) in 3 steps, with subsequent 50% overall yield. The nonprotected side-chain thiols (7a—d) were prepared from 5a—d by the Mitsunobu reaction and deacetylation. 1b -Methylcarbapenems bearing 5-methyl-4-mercaptopyrrolidinones were synthesized from PNB-protected carbapenem enolphosphate (8) and thiols (7a—d). Some effects of the chiral center in the C- 2 side chain were observed on in vitro  ctivities and pharmacokinetic parameters. Comparison of stereoisomers ndicated that 1a shows greater antibacterial activity than the others. In addition, the degradation rate of 1a with DHP-1 was slower than the others.

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List of Articles
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58 58. Asymmetric formal synthesis of (-)-formoterol and (-)-tamsulosin - Heterocycles - 2007, 2243 imagefile aziridine 2010-05-29 4812
57 57. Preparation of enantiopure 2-acylazetidines and their reactions with chloroformates - Tetrahedron Lett. 2007 48 269-271 imagefile aziridine 2010-05-17 3870
56 56. Selective reduction of C-C double bonds of 2-vinylaziridines:preparation of enantiomerically pure 2-alkylaziridines - Bull. Kor. Chem. Soc. 2009, 3123 imagefile aziridine 2010-05-12 3775
55 55. Dynamic Thermodynamic Resolution:Advantage by Separation of Equilibration and Resolution - Acc. Chem. Res., 2009, 42, 224 imagefile aziridine 2010-05-12 3194
54 54. The preparation of stable aziridinium ions and their ring-openings - Chem. Comm. 2008, 4363–4365 imagefile aziridine 2010-05-12 3778
53 53. Nucleophilic substitution of (sulfonyloxymethyl)aziridines: an asymmetric synthesis of both isomers of mexiletine - Tetrahedron 2008, 64, 11110 imagefile aziridine 2010-05-12 3229
52 52. Sphingosine 1-phosphate (S1P) induces shape change in rat C6 glioma cells through the S1P2 receptor: development of an agonist for S1P receptors - Journal of Pharmacy and Pharmacology 2007, 59, 1035-1041 imagefile aziridine 2010-05-12 3856
51 51. Selective Mono-BOC Protection of diamines - Synth. Comm. 2007, 37, 737-742 imagefile aziridine 2010-05-12 4892
50 50. Bis-styrylpyridine and bis-styrylbenzene derivatives as inhibitors for Aβ fibril formation - Bioorg. Med. Chem. Lett. 2007, 17, 1466-1470 imagefile aziridine 2010-05-12 3142
49 49. Dihydroxylation of 2-vinyl-aziridine: Efficient synthesis of D-ribo-phytosphingosine - Chem. Commun. 2007, 79-81 imagefile aziridine 2010-05-12 3715
48 48. Ring opening of 2-acylaziridines by acid chlorides - Tetrahedron 2006, 62, 8844-8849 imagefile aziridine 2010-05-12 3730
47 47. An efficient synthesis of chiral terminal 1,2-diamines using an enantiomerically pure [1-(10R)-methylbenzyl]aziridine-2-yl]methanol - Tetrahedron 2006, 62, 8393-8397 imagefile aziridine 2010-05-12 3178
46 46. Cyclo(Phe-Pro) Modulates the Expression of ompU in Vibrio spp. - Journal of Bacteriology 2006, 188, 6, 2214 imagefile aziridine 2010-05-12 3783
45 45. Synthesis of constrained ceramide analogs and their potent antileukemic activities - Bioorg. Med. Chem. Lett. 2006, 16, 1880-1883 imagefile aziridine 2010-05-12 4175
44 44. Addition reactions to chiral aziridine-2-carboxaldimine toward various enantiopure nitrogen-containing heterocycles - Tetrahedron. 2005, 9281 imagefile aziridine 2010-05-12 3790
43 43. Synthesis of Functionalized Bicyclic Triazoles from Chiral Aziridines - Synlett. 2005, 14, 2187 imagefile aziridine 2010-05-12 4075
42 42. Lewis acid-catalyzed stereospecific ring expansion of aziridine-2-carboxylates to imidazolidin-2-ones - Chem. Commun. 2005, 24, 3062 imagefile aziridine 2010-05-12 3175
41 41. Preparation of 2,3-diaminopropionate from ring opening of aziridine-2-carboxylate - Tetrahedron Lett. 2005, 46, 4407 imagefile aziridine 2010-05-12 4211
40 40. Synthesis and evaluation of sphingoid analogs as inhibitors of sphingosine kinases - Bioorg. Med. Chem. 2005, 13, 3475 imagefile aziridine 2010-05-12 3652
39 39. Stereoselective Addition of Nucleophiles to Aziridinyl-2-carboxaldimine - Bull. Kor. Chem. Soc. 2004, 1617 imagefile aziridine 2010-05-12 3125
38 38. Synthesis and antibacterial activity of arylpiperazinyl oxazolidinones with diversification of the N-substituents - Bioorg. Med. Chem. 2004, 3881 imagefile aziridine 2010-05-12 3459
37 37. Highly Stereoselective Addition of Organomagnesium Reagents to Aziridinyl-2-carboxaldimine: Preparation of Enantiopure 2-Aminomethylaziridines and 4,5-Disubstituted Imidazolidin-2-ones - Synlett. 2004, 489 imagefile aziridine 2010-05-12 3260
36 36. Dicyano{[(1S)-(1-phenylethyl)aziridine-2-yl]methanolato-κ2N,O}boron - Acta Cryst. (2003). C59, 0659-0660 imagefile aziridine 2010-05-12 3195
35 35. Efficient Synthesis of Enantiomerically Pure 2-Acylaziridines - J. Org. Chem. 2003, 68, 7675 imagefile aziridine 2010-05-12 3218
34 34. Hightlights of the Chemistry of Enantiomerically Pure Aziridine-2-Carboxylates - Aldrichimica Acta 2003, 36, 57 imagefile aziridine 2010-05-12 3634
33 33. A Novel Synthesis of 5-Functionalized Oxazolidin-2-ones from Enantiomerically Pure 2-Substituted N-[(R)-(+)-r-Methylbenzyl]aziridines - J. Org. Chem. 2003, 68, 104 imagefile aziridine 2010-05-12 3662
32 32. Novel Stereoselective Synthesis of Functionalized Oxazolidinones from Chiral Aziridines - J. Org. Chem. 2003, 68, 43 imagefile aziridine 2010-05-12 3162
31 31. Facile synthesis of β-anilinopropionates from lewis acid-induced N-methyleneanilines with ketene acetals - Syn. Comm. 2002, 32, 1495 imagefile aziridine 2010-05-12 3066
30 30. An Efficient Synthesis of N-Boc-D-Diphenylalanine from A Chiral Aziridine-2-Carboxylate - Heterocycles 2002, 57, 1143 imagefile aziridine 2010-05-12 3396
» 29. Syntheses of 1b -Methylcarbapenems Bearing 5-Methyl-4-hydroxypyrrolidinone - Chem. Pharm. Bull. 2002, 50, 415 imagefile aziridine 2010-05-12 3100


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