Aza-Wittig reaction of N-phosphorylalkyl phosphazenes with carbonyl compounds and phenylisocyanate. Synthesis of 4-amino-3-phosphoryl-2-azadienes and pyrazine-phosphonates

Tetrahedron

Volumn 59, Issue 15, 2003, Pages 2617-2623

  Palacios, Francisco ^a   Ochoa De Retana, Ana María ^a   Martínez De Marigorta, Eduardo ^a   Rodriguez, Marta ^a   Pagalday, Jaione ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

Aminophosphonates; Aza Wittig; Azadienes; Phosphazenes; Pyrazines; Pyrroles

Indexed keywords

2,5 BIS(DIETHOXYPHOSPHORYL)PYRAZINE; CARBONYL DERIVATIVE; CYANAMIDE; DIETHYL N (1 CYANOETHYLIDEN)AMINOMETHYLPHOSPHONATE; DIETHYL N (2 ALLYOXYBENZYLIDEN)AMINOMETHYLPHOSPHONATE; DIETHYL N (4 METHOXYBENZYLIDEN)AMINOMETHYLPHOSPHONATE; DIETHYL N (4 METHYLBENZYLIDEN)AMINOMETHYLPHOSPHONATE; DIETHYL N (4 NITROBENZYLIDEN)AMINOMETHYLPHOSPHONATE; DIETHYL [2 DIMETHYLAMINO 1 (4 METHYLBENZYLIDENE)AMINO]PHOSPHONATE; DIETHYL [2 DIMETHYLAMINO 1 [(2 ALLYLOXYBENZYLIDENE)AMINO]VINYL]PHOSPHONATE; DIETHYL [2 DIMETHYLAMINO 1 [(4 NITROBENZYLIDENE)AMINO]VINYL]PHOSPHONATE; ETHYL N [1 (DIETHOXYPHOSPHORYL) 2 DIMETHYLAMINOVINYL]CYANOFORMIMIDATE; FUNCTIONAL GROUP; IMINE; N,N DIMETHYLFORMAMIDE; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ACIDIFICATION; ARTICLE; CHEMICAL REACTION; PRIORITY JOURNAL; SUBSTITUTION REACTION; SYNTHESIS; WITTIG REACTION;

EID: 0037424849     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00337-5     Document Type: Article

References (103)

1. For reviews, see: (a) Jayakumar S., Ishar M.P.S., Mahajan M.P. Tetrahedron. 58:2002;379-471 (b) Tietze L.F., Kettschau G. Top. Curr. Chem. 189:1997;1-120 (c) Ghosez L. Stereocontrolled Organic Synthesis. 1994;Backwell, Oxford. pp 193-233 (d) Barluenga J., Tomás M. Adv. Heterocycl. Chem. 57:1993;1-78 (e) Boger D.L. Trost M., Paquete L.A. Comprehensive Organic Synthesis B. Vol. 5:1991;451-512 Pergamon, Oxford.
2. For reviews, see: (a) Jayakumar S., Ishar M.P.S., Mahajan M.P. Tetrahedron. 58:2002;379-471 (b) Tietze L.F., Kettschau G. Top. Curr. Chem. 189:1997;1-120 (c) Ghosez L. Stereocontrolled Organic Synthesis. 1994;Backwell, Oxford. pp 193-233 (d) Barluenga J., Tomás M. Adv. Heterocycl. Chem. 57:1993;1-78 (e) Boger D.L. Trost M., Paquete L.A. Comprehensive Organic Synthesis B. Vol. 5:1991;451-512 Pergamon, Oxford.
3. For reviews, see: (a) Jayakumar S., Ishar M.P.S., Mahajan M.P. Tetrahedron. 58:2002;379-471 (b) Tietze L.F., Kettschau G. Top. Curr. Chem. 189:1997;1-120 (c) Ghosez L. Stereocontrolled Organic Synthesis. 1994;Backwell, Oxford. pp 193-233 (d) Barluenga J., Tomás M. Adv. Heterocycl. Chem. 57:1993;1-78 (e) Boger D.L. Trost M., Paquete L.A. Comprehensive Organic Synthesis B. Vol. 5:1991;451-512 Pergamon, Oxford.
4. For reviews, see: (a) Jayakumar S., Ishar M.P.S., Mahajan M.P. Tetrahedron. 58:2002;379-471 (b) Tietze L.F., Kettschau G. Top. Curr. Chem. 189:1997;1-120 (c) Ghosez L. Stereocontrolled Organic Synthesis. 1994;Backwell, Oxford. pp 193-233 (d) Barluenga J., Tomás M. Adv. Heterocycl. Chem. 57:1993;1-78 (e) Boger D.L. Trost M., Paquete L.A. Comprehensive Organic Synthesis B. Vol. 5:1991;451-512 Pergamon, Oxford.
5. For reviews, see: (a) Jayakumar S., Ishar M.P.S., Mahajan M.P. Tetrahedron. 58:2002;379-471 (b) Tietze L.F., Kettschau G. Top. Curr. Chem. 189:1997;1-120 (c) Ghosez L. Stereocontrolled Organic Synthesis. 1994;Backwell, Oxford. pp 193-233 (d) Barluenga J., Tomás M. Adv. Heterocycl. Chem. 57:1993;1-78 (e) Boger D.L. Trost M., Paquete L.A. Comprehensive Organic Synthesis B. Vol. 5:1991;451-512 Pergamon, Oxford.
6. For recent contributions see: (a) Nicolau K.C., Nevalainen M., Safina B.S., Zak M., Bulat S. Angew. Chem., Int. Ed. 41:2002;1941-1945 (b) Moody C.J., Hughes R.A., Thompson S.P., Alcaraz L. Chem. Commun. 2002;1760-1761 (c) Jnoff E., Ghosez L. J. Am. Chem. Soc. 121:1999;2617-2618.
7. For recent contributions see: (a) Nicolau K.C., Nevalainen M., Safina B.S., Zak M., Bulat S. Angew. Chem., Int. Ed. 41:2002;1941-1945 (b) Moody C.J., Hughes R.A., Thompson S.P., Alcaraz L. Chem. Commun. 2002;1760-1761 (c) Jnoff E., Ghosez L. J. Am. Chem. Soc. 121:1999;2617-2618.
8. For recent contributions see: (a) Nicolau K.C., Nevalainen M., Safina B.S., Zak M., Bulat S. Angew. Chem., Int. Ed. 41:2002;1941-1945 (b) Moody C.J., Hughes R.A., Thompson S.P., Alcaraz L. Chem. Commun. 2002;1760-1761 (c) Jnoff E., Ghosez L. J. Am. Chem. Soc. 121:1999;2617-2618.
9. (a) Cheng Y., Ho E., Mariano P.S., Ammon H.L. J. Org. Chem. 50:1985;5678-5686.
10. (b) Venturini A., Joglar J., Fustero S., Gonzalez J. J. Org. Chem. 62:1997;3919-3926.
11. (a) Palacios F., Alonso C., Amezua P., Rubiales G. J. Org. Chem. 67:2002;1941-1946.
12. (b) Palacios F., Alonso C., Rubiales G., Ezpeleta J.M. Eur. J. Org. Chem. 2001;2115-2122
13. (c) Palacios F., Alonso C., Rubiales G. J. Org. Chem. 62:1997;1146-1152.
14. (a) Palacios F., Herrán E., Rubiales G., Ezpeleta J.M. J. Org. Chem. 67:2002;2131-2135.
15. (b) Palacios F., Herrán E., Rubiales G. J. Org. Chem. 64:1999;6239-6246.
16. (c) Palacios F., Pérez de Heredia I., Rubiales G. J. Org. Chem. 60:1995;2384-2390.
17. (d) Barluenga J., Ferrero M., Palacios F. Tetrahedron Lett. 29:1988;4863-4864.
18. (a) Pinho e Melo T.M.V.D., Fausto R., d'A Rocha Gonsalves A.M., Gilchrist A.M. J. Org. Chem. 63:1998;5350-5355.
19. (b) Balsamini C., Bedini A., Galarini R., Spadni G., Tarzia G., Hamdam M. Tetrahedron. 50:1994;12375-12394.
20. (c) d'A Rocha Gonsalves A.M., Pinho e Melo T.M.V.D., Gilchrist T.L. Tetrahedron. 50:1994;13709-13724.
21. (d) Wulff G., Böhnke H. Angew. Chem., Int. Ed. 25:1986;90-92.
22. (a) Smith A.B., Yager K.M., Taylor C.M. J. Am. Chem. Soc. 117:1995;10879-10888.
23. (b) Hirschmann R., Smith A.B., Taylor C.M., Benkovic P.A., Taylor S.D., Yager K.M., Spengler P.A., Benkovic S.J. Science. 265:1994;234-237.
24. (c) Cristau H.J., GenevisBorella A., Coulombeau A., Pirat J.L. Tetrahedron Lett. 42:2001;4491-4494.
25. (d) Georgiadis D., Dive V., Yiotakis A. J. Org. Chem. 66:2001;6604-6610.
26. (e) Meyer J.H., Bartlett P.A. J. Am. Chem. Soc. 120:1998;4600-4609.
27. (a) Toy A.D.F., Walsh E.N. Phosphorus Chemistry in Everyday Living. 1987;American Chemical Society, Washington DC
28. (b) Engel R. Handbook of Organophosphorus Chemistry. 1992;Marcel Dekker, New York.
29. (a) Palacios F., Aparicio D., de los Santos J.M. Tetrahedron. 52:1996;4857-4866.
30. (b) Stevens C., Gallant M., De Kimpe N. Tetrahedron Lett. 40:1999;3457-3460.
31. (c) Palacios F., Gil M.J., Martinez de Marigorta E., Rodriguez M. Tetrahedron. 56:2000;6319-6330.
32. (d) Palacios F., Gil M.J., Martinez de Marigorta E., Rodriguez M. Tetrahedron Lett. 40:1999;2411-2414.
33. For reviews see: (a) Wamhoff H., Richardt G., Stölben S. Adv. Heterocycl. Chem. 64:1995;159-249 (b) Molina P., Vilaplana M.J. Synthesis. 1994;1197-1218 (c) Eguchi S., Matsushita Y., Yamashita K. Org. Prep. Proced. Int. 24:1992;209-243 (d) Gololobov Y.G., Kaskhin L.F. Tetrahedron. 48:1992;1353-1406 (e) Barluenga J., Palacios F. Org. Prep. Proced. Int. 23:1991;1-59.
34. For reviews see: (a) Wamhoff H., Richardt G., Stölben S. Adv. Heterocycl. Chem. 64:1995;159-249 (b) Molina P., Vilaplana M.J. Synthesis. 1994;1197-1218 (c) Eguchi S., Matsushita Y., Yamashita K. Org. Prep. Proced. Int. 24:1992;209-243 (d) Gololobov Y.G., Kaskhin L.F. Tetrahedron. 48:1992;1353-1406 (e) Barluenga J., Palacios F. Org. Prep. Proced. Int. 23:1991;1-59.
35. For reviews see: (a) Wamhoff H., Richardt G., Stölben S. Adv. Heterocycl. Chem. 64:1995;159-249 (b) Molina P., Vilaplana M.J. Synthesis. 1994;1197-1218 (c) Eguchi S., Matsushita Y., Yamashita K. Org. Prep. Proced. Int. 24:1992;209-243 (d) Gololobov Y.G., Kaskhin L.F. Tetrahedron. 48:1992;1353-1406 (e) Barluenga J., Palacios F. Org. Prep. Proced. Int. 23:1991;1-59.
36. For reviews see: (a) Wamhoff H., Richardt G., Stölben S. Adv. Heterocycl. Chem. 64:1995;159-249 (b) Molina P., Vilaplana M.J. Synthesis. 1994;1197-1218 (c) Eguchi S., Matsushita Y., Yamashita K. Org. Prep. Proced. Int. 24:1992;209-243 (d) Gololobov Y.G., Kaskhin L.F. Tetrahedron. 48:1992;1353-1406 (e) Barluenga J., Palacios F. Org. Prep. Proced. Int. 23:1991;1-59.
37. For reviews see: (a) Wamhoff H., Richardt G., Stölben S. Adv. Heterocycl. Chem. 64:1995;159-249 (b) Molina P., Vilaplana M.J. Synthesis. 1994;1197-1218 (c) Eguchi S., Matsushita Y., Yamashita K. Org. Prep. Proced. Int. 24:1992;209-243 (d) Gololobov Y.G., Kaskhin L.F. Tetrahedron. 48:1992;1353-1406 (e) Barluenga J., Palacios F. Org. Prep. Proced. Int. 23:1991;1-59.
38. For recent contributions see: (a) Bell S.A., Meyer T.Y., Gelb S.J. J. Am. Chem. Soc. 124:2002;10698-10705 (b) Steiner S.J.H., Zacchini S., Richards P.I. Coord. Chem. Rev. 227:2002;193-216 (c) Andujar C., Perez I., Lopez F. Tetrahedron. 58:2002;2569-2575 (d) Rodima T., Kaljurand I., Pihl A., Maeemets V., Vahur I.L., Koppel I.A. J. Org. Chem. 67:2002;1873-1881.
39. For recent contributions see: (a) Bell S.A., Meyer T.Y., Gelb S.J. J. Am. Chem. Soc. 124:2002;10698-10705 (b) Steiner S.J.H., Zacchini S., Richards P.I. Coord. Chem. Rev. 227:2002;193-216 (c) Andujar C., Perez I., Lopez F. Tetrahedron. 58:2002;2569-2575 (d) Rodima T., Kaljurand I., Pihl A., Maeemets V., Vahur I.L., Koppel I.A. J. Org. Chem. 67:2002;1873-1881.
40. For recent contributions see: (a) Bell S.A., Meyer T.Y., Gelb S.J. J. Am. Chem. Soc. 124:2002;10698-10705 (b) Steiner S.J.H., Zacchini S., Richards P.I. Coord. Chem. Rev. 227:2002;193-216 (c) Andujar C., Perez I., Lopez F. Tetrahedron. 58:2002;2569-2575 (d) Rodima T., Kaljurand I., Pihl A., Maeemets V., Vahur I.L., Koppel I.A. J. Org. Chem. 67:2002;1873-1881.
41. For recent contributions see: (a) Bell S.A., Meyer T.Y., Gelb S.J. J. Am. Chem. Soc. 124:2002;10698-10705 (b) Steiner S.J.H., Zacchini S., Richards P.I. Coord. Chem. Rev. 227:2002;193-216 (c) Andujar C., Perez I., Lopez F. Tetrahedron. 58:2002;2569-2575 (d) Rodima T., Kaljurand I., Pihl A., Maeemets V., Vahur I.L., Koppel I.A. J. Org. Chem. 67:2002;1873-1881.
42. (a) Kato H., Ohmori K., Suzuki K. Synlett. 2001;1003-1005.
43. (b) Ariza X., Urpí F., Vilarrasa J. Tetrahedron Lett. 40:1999;7515-7517.
44. (c) Ariza X., Urpí F., Viladomat C., Vilarrasa J. Tetrahedron Lett. 39:1998;9101-9102.
45. (d) García J.J., Santoyo F., Vargas A. Synlett. 1997;265-266.
46. (e) Bosch I., Gonzalez A., Urpi F., Vilarrasa J. J. Org. Chem. 61:1996;5638-5643.
47. (a) Jiang B., Yang C.G., Wang J. J. Org. Chem. 67:2002;1396-1398.
48. (b) Molina P., Fresneda P.M., Delgado S., Bleda J.A. Tetrahedron Lett. 43:2002;1005-1007.
49. (c) Barthelemy S., Schneider S., Bannwarth W. Tetrahedron Lett. 43:2002;807-810.
50. (d) Turos G., Csampai A., Czugler M., Wamhoff H., Sohar P. J. Organomet. Chem. 634:2001;122-130.
51. (e) Alvarez R., Peinador C., Quintela J.M. Tetrahedron. 57:2001;5413-5420.
52. (a) Lopez F., Pelaez E., Palacios F., Barluenga J., García S., Tejerina B., García A. J. Org. Chem. 59:1994;1984-1992.
53. (b) Barluenga J., Merino I., Palacios F. Tetrahedron Lett. 30:1989;5493-5496.
54. (a) Palacios F., Legido M., Perez de Heredia I., Rubiales G. Heterocycles. 52:2000;1057-1064.
55. (b) Palacios F., Alonso C., Rubiales G. Tetrahedron. 51:1995;3683-3690.
56. (c) Barluenga J., López F., Palacios F. J. Organomet. Chem. 382:1990;61-67.
57. (d) Barluenga J., López F., Palacios F. Tetrahedon Lett. 28:1987;4327-4328.
58. Katritzky A.R., Zhang G., Jiang J. J. Org. Chem. 59:1994;4556-4560.
59. (a) Palacios F., Ochoa de Retana A.M., Pagalday J. Heterocycles. 40:1995;543-550.
60. (b) Gadja T., Matusiak M. Synthesis. 1992;367-368.
61. 16.
62. Alvarez-Ibarra C., Csàky A.G., Murcia C. J. Org. Chem. 63:1998;8763-8768.
63. Yuan C., Huang W. Synthesis. 1993;473-475.
64. Huang W., Zhang Y.-X., Yuang C. J. Chem. Soc., Perkin Trans. 1. 1996;1893-1895.
65. (a) Palacios F., Aparicio D., Vicario J. Eur. J. Org. Chem. 2002;4131-4136.
66. (b) Bazureau J.P., Jouneau S. Tetrahedron Lett. 40:1999;8097-8100.
67. (a) Palacios F., Ochoa de Retana A.M., Oyarzabal J. Tetrahedron. 55:1999;5947-5964.
68. (b) Bentrude W.G., Setzer W.N. Phosphrus-31 NMR Spectroscopy in Stereochemical Analysis. Organic Compounds and Metal Complexes. 1987;VCH, Florida. pp 365-389.
69. (a) Palacios F., Ochoa de Retana A.M., Gil J.I., Alonso J.M. Tetrahedron: Asymmetry. 13:2002;2541-2552.
70. (b) Palacios F., Aparicio D., Ochoa de Retana A.M., de los Santos J., Gil J.I., Alonso J.M. J. Org. Chem. 67:2002;7283-7288.
71. (c) Palacios F., Ochoa de Retana A.M., Martinez de Marigorta E., de los Santos J. Eur. J. Org. Chem. 2001;2401-2414.
72. (d) Palacios F., Ochoa de Retana A.M., Gil J.I., Ezpeleta J.M. J. Org. Chem. 65:2000;3213-3217
73. (e) Palacios F., Ochoa de Retana A.M., Gil J.I. Tetrahedron Lett. 41:2000;5363-5366.
74. (a) Palacios F., Aparicio D., García J., Vicario J., Ezpeleta J.M. Eur. J. Org. Chem. 2001;3357-3365.
75. (b) Palacios F., Aparicio D., de los Santos J.M., Vicario J. Tetrahedron. 57:2001;1961-1972.
76. (c) Palacios F., Aparicio D., de los Santos J.M. Tetrahedron. 55:1999;13767-13778
77. (d) Palacios F., Ochoa de Retana A.M., Oyarzabal J., Ezpeleta J.M. Tetrahedron. 54:1998;2281-2288.
78. (a) Palacios F., Ochoa de Retana A.M., Pascual S., López de Munain R. Tetrahedron Lett. 43:2002;5917-5919.
79. (b) Palacios F., Ochoa de Retana A.M., Gil J.I., López de Munain R. Org. Lett. 4:2002;2405-2408.
80. (c) Palacios F., Gil M.J., Martínez de Marigorta E., Rodríguez M. Tetrahedron. 56:2000;6319-6330.
81. (d) Palacios F., Ochoa de Retana A.M., Oyarzabal J. Tetrahedron. 55:1999;5947-5964.
82. (e) Palacios F., Aparicio D., Ochoa de Retana A.M., de los Santos J.M., García J., Oyarzabal J. Tetrahedron. 55:1999;3105-3116.
83. (f) Palacios F., Aparicio D., Garcia J. Tetrahedron. 54:1998;1647-1656.
84. For recent reviews on pyrazines see: (a) McCullough K.L. Sainsbury M. 2nd ed. Heterocyclic Compounds. Rodd's Chemistry of Carbon Compounds. Vol. 4:2000;99-171 Elsevier, Amsterdam. 2nd Suppl., (Pt. I-J) (b) Urban S., Hickford S.J.H., Blunt J.W., Munro M.H.G. Curr. Org. Chem. 4:2000;765-807 (c) Ohta A., Aoyagi Y. Rev. Heteroat. Chem. 18:1998;141-167 (d) Sato N. Katritzky A.R., Rees C.W., Boulton A.J. Comprehensive Heterocyclic Chemistry II. Vol. 6:1996;233-278 Elsevier, Oxford.
85. For recent reviews on pyrazines see: (a) McCullough K.L. Sainsbury M. 2nd ed. Heterocyclic Compounds. Rodd's Chemistry of Carbon Compounds. Vol. 4:2000;99-171 Elsevier, Amsterdam. 2nd Suppl., (Pt. I-J) (b) Urban S., Hickford S.J.H., Blunt J.W., Munro M.H.G. Curr. Org. Chem. 4:2000;765-807 (c) Ohta A., Aoyagi Y. Rev. Heteroat. Chem. 18:1998;141-167 (d) Sato N. Katritzky A.R., Rees C.W., Boulton A.J. Comprehensive Heterocyclic Chemistry II. Vol. 6:1996;233-278 Elsevier, Oxford.
86. For recent reviews on pyrazines see: (a) McCullough K.L. Sainsbury M. 2nd ed. Heterocyclic Compounds. Rodd's Chemistry of Carbon Compounds. Vol. 4:2000;99-171 Elsevier, Amsterdam. 2nd Suppl., (Pt. I-J) (b) Urban S., Hickford S.J.H., Blunt J.W., Munro M.H.G. Curr. Org. Chem. 4:2000;765-807 (c) Ohta A., Aoyagi Y. Rev. Heteroat. Chem. 18:1998;141-167 (d) Sato N. Katritzky A.R., Rees C.W., Boulton A.J. Comprehensive Heterocyclic Chemistry II. Vol. 6:1996;233-278 Elsevier, Oxford.
87. For recent reviews on pyrazines see: (a) McCullough K.L. Sainsbury M. 2nd ed. Heterocyclic Compounds. Rodd's Chemistry of Carbon Compounds. Vol. 4:2000;99-171 Elsevier, Amsterdam. 2nd Suppl., (Pt. I-J) (b) Urban S., Hickford S.J.H., Blunt J.W., Munro M.H.G. Curr. Org. Chem. 4:2000;765-807 (c) Ohta A., Aoyagi Y. Rev. Heteroat. Chem. 18:1998;141-167 (d) Sato N. Katritzky A.R., Rees C.W., Boulton A.J. Comprehensive Heterocyclic Chemistry II. Vol. 6:1996;233-278 Elsevier, Oxford.
88. For recent contributions see: (a) Gohlke H., Gundisch D., Schwarz S., Seitz G., Tilotta M.C., Wegge T. J. Med. Chem. 45:2002;1064-1072 (b) Ragnarsson U., Grehn L., Maia H.L., Monteiro L.S. Org. Lett. 3:2001;2021-2023 (c) Liu W., Wise D.S., Townsend L.B. J. Org. Chem. 66:2001;4783-4786 (d) Cavalier J.F., Burton M., Dussart F., Marchand F., Rees J.F., Marchant-Brynaert J. Bioorg. Med. Chem. 9:2001;1037-1044 (e) Shibata K., Fukuwatari T., Sugimoto E. Biosci. Biotechnol. Biochem. 65:2001;1339-1346.
89. For recent contributions see: (a) Gohlke H., Gundisch D., Schwarz S., Seitz G., Tilotta M.C., Wegge T. J. Med. Chem. 45:2002;1064-1072 (b) Ragnarsson U., Grehn L., Maia H.L., Monteiro L.S. Org. Lett. 3:2001;2021-2023 (c) Liu W., Wise D.S., Townsend L.B. J. Org. Chem. 66:2001;4783-4786 (d) Cavalier J.F., Burton M., Dussart F., Marchand F., Rees J.F., Marchant-Brynaert J. Bioorg. Med. Chem. 9:2001;1037-1044 (e) Shibata K., Fukuwatari T., Sugimoto E. Biosci. Biotechnol. Biochem. 65:2001;1339-1346.
90. For recent contributions see: (a) Gohlke H., Gundisch D., Schwarz S., Seitz G., Tilotta M.C., Wegge T. J. Med. Chem. 45:2002;1064-1072 (b) Ragnarsson U., Grehn L., Maia H.L., Monteiro L.S. Org. Lett. 3:2001;2021-2023 (c) Liu W., Wise D.S., Townsend L.B. J. Org. Chem. 66:2001;4783-4786 (d) Cavalier J.F., Burton M., Dussart F., Marchand F., Rees J.F., Marchant-Brynaert J. Bioorg. Med. Chem. 9:2001;1037-1044 (e) Shibata K., Fukuwatari T., Sugimoto E. Biosci. Biotechnol. Biochem. 65:2001;1339-1346.
91. For recent contributions see: (a) Gohlke H., Gundisch D., Schwarz S., Seitz G., Tilotta M.C., Wegge T. J. Med. Chem. 45:2002;1064-1072 (b) Ragnarsson U., Grehn L., Maia H.L., Monteiro L.S. Org. Lett. 3:2001;2021-2023 (c) Liu W., Wise D.S., Townsend L.B. J. Org. Chem. 66:2001;4783-4786 (d) Cavalier J.F., Burton M., Dussart F., Marchand F., Rees J.F., Marchant-Brynaert J. Bioorg. Med. Chem. 9:2001;1037-1044 (e) Shibata K., Fukuwatari T., Sugimoto E. Biosci. Biotechnol. Biochem. 65:2001;1339-1346.
92. For recent contributions see: (a) Gohlke H., Gundisch D., Schwarz S., Seitz G., Tilotta M.C., Wegge T. J. Med. Chem. 45:2002;1064-1072 (b) Ragnarsson U., Grehn L., Maia H.L., Monteiro L.S. Org. Lett. 3:2001;2021-2023 (c) Liu W., Wise D.S., Townsend L.B. J. Org. Chem. 66:2001;4783-4786 (d) Cavalier J.F., Burton M., Dussart F., Marchand F., Rees J.F., Marchant-Brynaert J. Bioorg. Med. Chem. 9:2001;1037-1044 (e) Shibata K., Fukuwatari T., Sugimoto E. Biosci. Biotechnol. Biochem. 65:2001;1339-1346.
93. (a) LaCour T.G., Guo C., Boyd M.R., Fuchs P.L. Org. Lett. 2:2000;33-36.
94. (b) Basler S., Brunck A., Jautelat R., Winterfeldt E. Helv. Chim. Acta. 83:2000;1854-1880.
95. (c) LaCour T.G., Guo C., Ma S., Jeong J.U., Boyd M.R., Matsunaga S., Fusetani N., Fuchs P.L. Bioorg. Med. Chem. Lett. 9:1999;2587-2592.
96. (d) Guo C., Bhandaru S., Fuchs P.L., Boyd M.R. J. Am. Chem. Soc. 118:1996;10672-10673.
97. (a) Suzuki Y., Suzuki A., Tamaru A., Katsukawa C., Oda H. J. Clin. Microbiol. 40:2002;501-507.
98. (b) Zhang Y., Permar S., Sun Z. J. Clin. Microbiol. 40:2002;42-49.
99. (c) Bothamley G. Drug Saf. 24:2001;553-565.
100. (d) Zimhony O., Cox J.S., Welch J.T., Vilcheze C., Jacobs W.R. Nat. Med. (N.Y.). 6:2000;1043-1047.
101. (a) Cynamon M.H., Speirs R.J., Welch J.T. Antimicrob. Agents Chemother. 42:1998;462-463.
102. (b) Bergmann K.E., Cynamon M.H., Welch J.T. J. Med. Chem. 39:1996;3394-3400
103. (c) Speirs R.J., Welch J.T., Cynamon M.H. Antimicrob. Agents Chemother. 39:1995;1269-1271.