Using 1,1- and 1,n-ADEQUATE 2D NMR Data in Structure Elucidation Protocols

Annual Reports on NMR Spectroscopy

Volumn 74, Issue , 2011, Pages 215-291

  Martin, Gary E ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

1,1 ADEQUATE; 1,n ADEQUATE; Carbon carbon correlation; Generalized indirect covariance; N,1 ADEQUATE; N,m ADEQUATE; Structure elucidation; Unsymmetrical indirect covariance

Indexed keywords

EID: 80053296618     PISSN: 00664103     EISSN: None     Source Type: Book Series    
DOI: 10.1016/B978-0-08-097072-1.00005-4     Document Type: Chapter

References (103)

1. Reynolds W.F., Enriquez R.G. J. Nat. Prod. 2002, 65:221-244.
2. Martin G.E., Hadden C.E., Russell D.J. Solution NMR spectroscopy. Handbook of Spectroscopy 2003, Vol. 1:209-268. Wiley-VCH.
3. Bross-Walch N., Kühn T., Moskau D., Zerbe O. Chem. Biodiversity 2005, 2:147-177.
4. Lohr L.L., Marquez B.L., Martin G.E. Nuclear magnetic resonance spectroscopy. Comprehensive Analytical Chemistry 2007, Vol. 47:259-318. Elsevier, Amsterdam.
5. Claridge T.D.W. High-Resolution NMR Techniques in Organic Chemistry 1999, Pergamon, Amsterdam, pp. 224-239.
6. Reynolds W.F., McLean S., Tay L.-L., Yu M., Enriquez R.G., Estwick D.M., Pascoe K.O. Magn. Reson. Chem. 1997, 35:455-462.
7. Bax A., Summers M.F. J. Am. Chem. Soc. 1986, 108:2093.
8. Crouch R.C., Llanos W., Mehr K.G., Hadden C.E., Russell D.J., Martin G.E. Magn. Reson. Chem. 2001, 39:555-563.
9. Martin G.E., Hadden C.E. Magn. Reson. Chem. 2000, 38:251-256.
10. 15 N heteronuclear shift correlation. Annual Reports on NMR Spectroscopy 2005, Vol. 55:1-119. G.A. Webb (Ed.).
11. Marek R., Lyčka A. Curr. Org. Chem. 2002, 6:35-66.
12. Marek R., Lyčka A., Kohlemainen E., Sievanen E., Toušek J. Curr. Org. Chem. 2007, 11:1154-1205.
13. 15 N NMR spectroscopy in alkaloid chemistry. Modern Alkaloids: Structure, Isolation, Synthesis and Biology 2008, 409-476. Wiley, New York. E. Fattorusso, O. Taglialatela-Scafati (Eds.).
14. Reynolds W.F., Hughes D.W., Perpick-Dumont M., Enriquez R.G. J. Magn. Reson. 1985, 63:413-417.
15. Krishnamurthy V.V., Russell D.J., Hadden C.E., Martin G.E. J. Magn. Reson. 2000, 146:232-239.
16. Nyberg N.T., Duus J.O., Sørensen O.W. J. Am. Chem. Soc. 2005, 127:6154-6155.
17. Nyberg N.T., Duus J.O., Sørensen O.W. Magn. Reson. Chem. 2005, 43:971-974.
18. Benie A.J., Sørensen O.W. J. Magn. Reson. 2007, 184:315-321.
19. Wagner R., Berger S. Magn. Reson. Chem. 1998, 36(S19):S44-S46.
20. Martin G.E., Hadden C.E., Crouch R.C., Krishnamurthy V.V. Magn. Reson. Chem. 1999, 37:517-528.
21. Hadden C.E., Martin G.E., Krishnamurthy V.V. J. Magn. Reson. 1999, 140:274-280.
22. Hadden C.E., Martin G.E., Krishnamurthy V.V. Magn. Reson. Chem. 2000, 38:143-147.
23. Martin G.E. Qualitative and quantitative exploitation of heteronuclear coupling constants. Annual Reports on NMR Spectroscopy 2002, Vol. 46:37-100. Academic Press, New York.
24. Bax A., Freeman R., Frenkiel T.A. J. Am. Chem. Soc. 1981, 103:2102-2104.
25. Turner D.L. J. Magn. Reson. 1983, 49:175-178.
26. Bax A., Mareci T.H. J. Magn. Reson. 1983, 535:360-363.
27. Bodenhausen G., Kogler H., Ernst R.R. J. Magn. Reson. 1984, 58:370-399.
28. Martin G.E. Cryogenic NMR probes: applications. Encyclopedia of Nuclear Magnetic Resonance, Vol. 9: Advances in NMR 2002, 33-35. D.M. Grant, R.K. Harris (Eds.).
29. Martin G.E. Microprobes and methodologies for spectral assignments: applications. Encyclopedia of Nuclear Magnetic Resonance, Vol. 9: Advances in NMR 2002, 98-112. D.M. Grant, R.K. Harris (Eds.).
30. Martin G.E. Small-volume and high-sensitivity NMR probes. Annual Reports on NMR Spectroscopy 2005, Vol. 56:1-96. G.A. Webb (Ed.).
31. Keller P., Vogele K. J. Magn. Reson. 1986, 68:389-392.
32. Sørensen O.W., Freeman R., Frenkiel T.A., Mareci T.H., Shuck R. J. Magn. Reson. 1982, 46:180-184.
33. Sparks S.W., Ellis P.D. J. Magn. Reson. 1985, 62:1-11.
34. Kessler H., Bermel W., Griesinger C. J. Magn. Reson. 1985, 62:573-579.
35. Kessler H., Bermel W., Griesinger C., Hertl P., Streich E., Rieker H. J. Org. Chem. 1986, 51:596-612.
36. Gosser Y.Q., Howard K.P., Prestegard J.H. J. Magn. Reson. 1993, 101B:126-133.
37. Chung J., Tolman J.R., Howard K.P., Prestegard J.H. J. Magn. Reson. 1993, 102B:137-147.
38. Pratum J.K., Moore B.S. J. Magn. Reson. 1993, 102B:91-97.
39. Weigelt J., Otting G. J. Magn. Reson. 1995, 113A:128-130.
40. Köck M., Rief B., Fenical W., Griesinger C. Tetrahedron Lett. 1996, 37:363-366.
41. Reif B., Köck M., Kerssebaum R., Kang H., Fenical W., Griesinger C. J. Magn. Reson. 1996, 118A:282-285.
42. Williamson R.T., Marquez B.L., Gerwick W.H., Koehn F.E. Magn. Reson. Chem. 2001, 39:544-548.
43. Köck M., Kerssebaum R., Bermel W. Magn. Reson. Chem. 2003, 41:65-69.
44. Kövér K., Forgó P. J. Magn. Reson. 2004, 166:47-52.
45. Thiele C.M., Bermel W. Magn. Reson. Chem. 2007, 45:889-894.
46. Parella T., Sánchez-Ferrando F. J. Magn. Reson. 2004, 166:123-128.
47. Wray V. Carbon-carbon coupling constants: a compilation of data and a practical guide. Progress in Nuclear Magnetic Resonance Spectroscopy 1979, Vol. 13:177-256.
48. 13 C spin-spin coupling constants. Annual Reports on NMR Spectroscopy 1995, Vol. 30:131-230. Academic Press, New York. G.A. Webb (Ed.).
49. Cheatham S., Kline M., Sasaki R.R., Blinov K., Elyashberg M.E., Molodtsov S.G. Magn. Reson. Chem. 2010, 48:571-574.
50. Myer S.W., Köck M. J. Nat. Prod. 2008, 71:1524-1529.
51. Hilton B.D., Martin G.E. J. Nat. Prod. 2010, 73:1465-1469.
52. Martin G.E., Hilton B.D., Blinov K.A. Magn. Reson. Chem. 2011, 49:248-252.
53. Martin G.E., Hilton B.D., Willcott M.R., Blinov K.A. Magn. Reson. Chem. 2011, 49:350-358.
54. Martin G.E., Hilton B.D., Blinov K.A. J. Nat. Prod. 2011, submitted for publication.
55. Snyder D.A., Brüschweiler R. Multidimensional correlation spectroscopy by covariance NMR. Multidimensional NMR Methods in the Solution State 2010, 97-105. John Wiley and Sons, Ltd., Chichester. G.A. Morris, J.W. Emsley (Eds.).
56. Lindel T., Junker J., Köck M. J. Mol. Model. 1997, 3:364-368.
57. Reif B., Köck M., Kerssebaum R., Schleucher J., Griesinger C. J. Magn. Reson. 1996, 112B:295-301.
58. Junker J., Maier W., Lindel T., Köck M. Org. Lett. 1999, 1:737-740.
59. Knaack M., Emig P., Bats J.W., Kiesel M., Müller A., Günther E. Eur. J. Org. Chem. 2001, 3843-3847.
60. Williamson R.T., Boulanger A., Vulpanovici A., Roberts M.A., Gerwick W.H. J. Org. Chem. 2002, 67:7927-7936.
61. Okabe T., Nomoto K., Funabashi H., Okuda S., Suzuki H., Tanaka N. J. Antibiot. 1985, 38:1333-1336.
62. Leo P.-M., Morin C., Philouze C. Org. Lett. 2002, 4:2711-2714.
63. Tatsuta K., Ozeki H., Yamaguchi M., Tanaka M., Okui T. Tetrahedron Lett. 1990, 31:5495-5498.
64. Williamson R.T., McDonald L.A., Barbieri L.R., Carter G.T. Org. Lett. 2002, 4:4659-4662.
65. He H., Janso J.E., Williamson R.T., Yang H.Y., Carter G.T. J. Org. Chem. 2003, 68:6079-6082.
66. Rubio E., Merino I., Garcia A.-B., Cabal M.-P., Ribas C., Bayod-Jasanda M. Magn. Reson. Chem. 2005, 43:269-282.
67. Godevac D., Mandić B., Vajs V., Menkković N., Macura S., Milosavljević S. Magn. Reson. Chem. 2006, 44:731-735.
68. Abdeljebber L.H., Humam M., Christen P., Jennerat D., Vitorg B., Amzazl S., Benjouad A., Hostettman K., Bekkouche K. Helv. Chim. Acta 2007, 90:346-352.
69. Dang H.V., Habib N.S., Kappe T., Zangger K., Stadlbauer W. J. Heterocyclic Chem. 2007, 44:161-165.
70. Wright A.D., Nielson J.L., Tapiolas D.M., Motti C.A., Ovenden S.P.B., Kearns P.S., Liptrot C.H. Mar. Drugs 2009, 7:565-575.
71. Januar H.I., Chasanah E., Motti C.A., Tapiolas D.M., Liptot C.H., Wright A.D. Mar. Drugs 2010, 8:2142-2152.
72. Schraml J., Kubec R., Kučerová P. Magn. Reson. Chem. 2011, 49:147-150.
73. Martin G.E., Hilton B.D., Willcott M.R., Blinov K.A. Magn. Reson. Chem. 2011, 49. in press.
74. Köck M., Reif B., Gerlach M., Reggelin M. Molecules 1996, 1:41-45.
75. Reif B., Kock M., Kerssebaum R., Schleucher J., Griesinger C. J. Magn. Reson. 1996, 112B:295-301.
76. Krividin L.B., Della E.W. Prog. NMR Spectrosc. 1991, 23:301-610.
77. Keller P., Bogele K. J. Magn. Reson. 1986, 68:389-392.
78. Pratum T.K., Moore B.S. J. Magn. Reson. 1993, 102B:91-97.
79. Wright J., Otting G. J. Magn. Reson. 1995, 113A:128-130.
80. G. E. Martin, C. W. Anklin and W. Bermel, unpublished results.
81. G. E. Martin, unpublished results.
82. Brüschweiler R., Zhang F. J. Chem. Phys. 2004, 120:5253-5260.
83. Brüschweiler R. J. Chem. Phys. 2004, 121:409-414.
84. Trbovic N., Smirnov S., Zhang F., Brüschweiler R. J. Magn. Reson. 2004, 171:277-283.
85. Zhang F., Brüschweiler R. J. Am. Chem. Soc. 2004, 126:13180-13181.
86. Blinov K.A., Larin N.I., Williams W.J., Mills K.A., Martin G.E. J. Heterocyclic Chem. 2006, 43:163-166.
87. Blinov K.A., Larin N.I., Williams A.J., Zell M., Martin G.E. Magn. Reson. Chem. 2006, 44:107-109.
88. Kupče Ē., Freeman R. J. Am. Chem. Soc. 2008, 128:6020-6021.
89. Freeman R., Kupče Ē. Multidimensional NMR by projection-reconstruction. Multidimensional NMR Methods in the Solution State 2010, 73-83. John Wiley and Sons, Ltd., Chichester. G.A. Morris, J.W. Emsley (Eds.).
90. Aue W.P., Barotholdi E., Ernst R.R. J. Chem. Phys. 1976, 64:2229-2251.
91. Martin G.E., Hilton B.D., Irish P.A., Blinov K.A., Williams A.J. J. Nat. Prod. 2007, 70:1393-1396.
92. Martin G.E., Hilton B.D., Blinov K.A., Williams A.J. J. Heterocyclic Chem. 2008, 45:1109-1113.
93. Blinov K.A., Williams A.J., Hilton B.D., Irish P.A., Martin G.E. Magn. Reson. Chem. 2007, 48:544-546.
94. Martin G.E., Irish P.A., Hilton B.D., Blinov K.A., Williams A.J. Magn. Reson. Chem. 2007, 45:624-627.
95. Martin G.E., Hilton B.D., Irish P.A., Blinov K.A., Williams A.J. Magn. Reson. Chem. 2007, 45:883-888.
96. Martin G.E., Hilton B.D., Irish P.A., Blinov K.A., Williams A.J. J. Heterocyclic Chem. 2007, 44:1219-1222.
97. Martin G.E., Hilton B.D., Blinov K.A., Williams A.J. J. Nat. Prod. 2007, 70:1966-1970.
98. Snyder D.A., Brüschweiler R. J. Chem. Phys. A 2009, 113:12898-12903.
99. Martin G.E. J. Heterocyclic Chem. 2011, 48. in press.
100. Martin G.E., Sunseri D. J. Pharm. Biomed. Anal. 2011, 55:895-901.
101. Martin G.E., Hilton B.D., Blinov K.A., Williams A.J. Magn. Reson. Chem. 2008, 46:138-143.
102. Martin G.E., Feng W., Hilton B.D. J. Heterocyclic Chem. 2011, 48:948-951.
103. Hilton B.D., Martin G.E. J. Heterocyclic Chem. 2011, 48. in press.