-
1
-
-
15444378803
-
-
Nicolaou, K. C.; Snyder, S. A. Angew. Chem., Int. Ed. 2005, 44, 1012-1044.
-
(2005)
Angew. Chem., Int. Ed
, vol.44
, pp. 1012-1044
-
-
Nicolaou, K.C.1
Snyder, S.A.2
-
4
-
-
0033525048
-
-
Matsumori, N.; Kaneno, D.; Murata, M.; Nakamura, H.; Tachibana, K. J. Org. Chem. 1999, 64, 866-876.
-
(1999)
J. Org. Chem
, vol.64
, pp. 866-876
-
-
Matsumori, N.1
Kaneno, D.2
Murata, M.3
Nakamura, H.4
Tachibana, K.5
-
5
-
-
0942277395
-
-
For a review on determining absolute configurations by NMR see
-
For a review on determining absolute configurations by NMR see: Seco, J. M.; Quiñoá, E.; Riguera, R. Chem. Rev. 2004, 7, 17-117.
-
(2004)
Chem. Rev
, vol.7
, pp. 17-117
-
-
Seco, J.M.1
Quiñoá, E.2
Riguera, R.3
-
6
-
-
23644460869
-
-
(a) Wolfender, J.-L.; Queiroz, E. F.; Hostettmann, K. Magn. Reson. Chem. 2005, 43, 697-709.
-
(2005)
Magn. Reson. Chem
, vol.43
, pp. 697-709
-
-
Wolfender, J.-L.1
Queiroz, E.F.2
Hostettmann, K.3
-
7
-
-
46749152580
-
-
(b) Bugni, T. S.; Richards, B.; Bhoite, L.; Cimbora, D.; Harper, M. K.; Ireland, C. M. J. Nat. Prod. 2008, 71, 1095-1098.
-
(2008)
J. Nat. Prod
, vol.71
, pp. 1095-1098
-
-
Bugni, T.S.1
Richards, B.2
Bhoite, L.3
Cimbora, D.4
Harper, M.K.5
Ireland, C.M.6
-
8
-
-
0019469697
-
-
Rinehart, K. L., Jr.; Gloer, J. B.; Hughes, R. G., Jr.; Renis, H. E.; McGovren, J. P.; Swynenberg, E. B.; Stringfellow, D. A.; Kuentzel, S. L.; Li, L. H. Science 1981, 212, 933-935.
-
(a) Rinehart, K. L., Jr.; Gloer, J. B.; Hughes, R. G., Jr.; Renis, H. E.; McGovren, J. P.; Swynenberg, E. B.; Stringfellow, D. A.; Kuentzel, S. L.; Li, L. H. Science 1981, 212, 933-935.
-
-
-
-
9
-
-
0019470678
-
-
(b) Rinehart, K. L., Jr.; Gloer, J. B.; Cook, J. C., Jr.; Mizsak, S. A.; Scahill, T. A. J. Am. Chem. Soc. 1981, 103, 1857-1859.
-
(1981)
J. Am. Chem. Soc
, vol.103
, pp. 1857-1859
-
-
Rinehart Jr., K.L.1
Gloer, J.B.2
Cook Jr., J.C.3
Mizsak, S.A.4
Scahill, T.A.5
-
10
-
-
0033961890
-
-
Vervoort, H.; Fenical, W.; de Epifanio, R. J. Org. Chem. 2000, 65, 782-792.
-
(2000)
J. Org. Chem
, vol.65
, pp. 782-792
-
-
Vervoort, H.1
Fenical, W.2
de Epifanio, R.3
-
11
-
-
0028598490
-
-
Stratmann, K.; Burgoyne, D. L.; Moore, R. E.; Patterson, G. M. L.; Smith, C. D. J. Org. Chem. 1994, 59, 7219-7226.
-
(1994)
J. Org. Chem
, vol.59
, pp. 7219-7226
-
-
Stratmann, K.1
Burgoyne, D.L.2
Moore, R.E.3
Patterson, G.M.L.4
Smith, C.D.5
-
12
-
-
13844312018
-
-
Zuo, Z.; Luo, X.; Zhu, W.; Shen, J.; Shen, X.; Jiang, H.; Chen, K. Bioorg. Med. Chem. 2005, 13, 2121-2131.
-
(2005)
Bioorg. Med. Chem
, vol.13
, pp. 2121-2131
-
-
Zuo, Z.1
Luo, X.2
Zhu, W.3
Shen, J.4
Shen, X.5
Jiang, H.6
Chen, K.7
-
13
-
-
0026468661
-
-
Fehrentz, J. A.; Chromier, B.; Bignon, E.; Venaud, S.; Chemann, J. C.; Nisato, D. Biochem. Biophys. Res. Commun. 1992, 188, 865-872.
-
(1992)
Biochem. Biophys. Res. Commun
, vol.188
, pp. 865-872
-
-
Fehrentz, J.A.1
Chromier, B.2
Bignon, E.3
Venaud, S.4
Chemann, J.C.5
Nisato, D.6
-
14
-
-
0033619850
-
-
Lee, J.; Kobayashi, Y.; Tezuka, K.; Kishi, Y. Org. Lett. 1999, 1, 2181-2184.
-
(1999)
Org. Lett
, vol.1
, pp. 2181-2184
-
-
Lee, J.1
Kobayashi, Y.2
Tezuka, K.3
Kishi, Y.4
-
15
-
-
0042844745
-
-
Williams, P. G.; Yoshida, W. Y.; Moore, R. E.; Paul, V. J. J. Nat. Prod. 2003, 66, 1006-1009.
-
(2003)
J. Nat. Prod
, vol.66
, pp. 1006-1009
-
-
Williams, P.G.1
Yoshida, W.Y.2
Moore, R.E.3
Paul, V.J.4
-
16
-
-
0001476761
-
-
Harris, B. D.; Bhat, K. L.; Joullie, M. M. Tetrahedron Lett. 1987, 28, 2837-2840.
-
(1987)
Tetrahedron Lett
, vol.28
, pp. 2837-2840
-
-
Harris, B.D.1
Bhat, K.L.2
Joullie, M.M.3
-
18
-
-
13444252571
-
-
Ori, M.; Toda, N.; Takami, K.; Tago, K.; Kogen, H. Tetrahedron 2005, 61, 2075-2104.
-
(2005)
Tetrahedron
, vol.61
, pp. 2075-2104
-
-
Ori, M.1
Toda, N.2
Takami, K.3
Tago, K.4
Kogen, H.5
-
20
-
-
21844465721
-
-
The stereochemistry of 24a was determined by conversion to the oxazolidinone derivative through treatment with triphosgene.The stereochemistry was then assigned via analysis of the JH3,H4 coupling constant. See: Wang, M.; Chen, Y.; Lou, L.; Tang, W.; Wang, X.; Shen, J. Tetrahedron Lett. 2005, 46, 5309-5312.
-
The stereochemistry of 24a was determined by conversion to the oxazolidinone derivative through treatment with triphosgene.The stereochemistry was then assigned via analysis of the JH3,H4 coupling constant. See: Wang, M.; Chen, Y.; Lou, L.; Tang, W.; Wang, X.; Shen, J. Tetrahedron Lett. 2005, 46, 5309-5312.
-
-
-
-
21
-
-
85069130017
-
-
A comparison of carbon and proton chemical shifts with the nature of the side chain (polar, nonpolar, aromatic, branched, etc) provided no predictive trend either
-
A comparison of carbon and proton chemical shifts with the nature of the side chain (polar, nonpolar, aromatic, branched, etc) provided no predictive trend either.
-
-
-
-
22
-
-
33845280841
-
-
There are reports of using 3JH3,H4 values for the relative stereochemical assignment of an Ala-Sta derivative (4-methylcarnitine: Comber, R. N.; Brouillette, W. J. J. Org. Chem. 1988 53 1121-1122), but based on our data (see the Supporting Information) this is not a general trend
-
There are reports of using 3JH3,H4 values for the relative stereochemical assignment of an Ala-Sta derivative (4-methylcarnitine: Comber, R. N.; Brouillette, W. J. J. Org. Chem. 1988 53 1121-1122), but based on our data (see the Supporting Information) this is not a general trend
-
-
-
-
24
-
-
0000253239
-
-
Heathcock, C. H.; Pirrung, M. C.; Sohn, J. E. J. Org. Chem. 1979, 44, 4294-4299.
-
(1979)
J. Org. Chem
, vol.44
, pp. 4294-4299
-
-
Heathcock, C.H.1
Pirrung, M.C.2
Sohn, J.E.3
-
25
-
-
85069134528
-
-
At 500 MHz, the 1H NMR spectra for these compounds were second order
-
At 500 MHz, the 1H NMR spectra for these compounds were second order.
-
-
-
-
26
-
-
85069129454
-
-
Spin simulations were done with MestreC 4.9.8.0 in an iterative fashion comparing with the experimental spectra until identical patterns were obtained. Experimental data were used as a constraint in these simulations when possible, i.e., δH3, 2JH2u,H2d, 3JH3,H2d + 3JH3,H2u, ca. δH2.
-
Spin simulations were done with MestreC 4.9.8.0 in an iterative fashion comparing with the experimental spectra until identical patterns were obtained. Experimental data were used as a constraint in these simulations when possible, i.e., δH3, 2JH2u,H2d, 3JH3,H2d + 3JH3,H2u, ca. δH2.
-
-
-
-
27
-
-
85069133914
-
-
A Scifinder Scholar search for the basic carbon skeleton yielded approximately 10 000 compounds, but the utility of this literature NMR data varied greatly. For example, H2-2 was frequently reported as a multiplet spanning a considerable chemical shift range. This indicated the methylene protons were probably diastereotopic (otherwise H2-2 would be a simple doublet), but provided no coupling constant information for comparison.
-
A Scifinder Scholar search for the basic carbon skeleton yielded approximately 10 000 compounds, but the utility of this literature NMR data varied greatly. For example, H2-2 was frequently reported as a multiplet spanning a considerable chemical shift range. This indicated the methylene protons were probably diastereotopic (otherwise H2-2 would be a simple doublet), but provided no coupling constant information for comparison.
-
-
-
-
28
-
-
0028917624
-
-
Sakai, R.; Stroh, J. G.; Sullins, D. W.; Rinehart, K. L. J. Am. Chem. Soc. 1995, 117, 3734-3748.
-
(1995)
J. Am. Chem. Soc
, vol.117
, pp. 3734-3748
-
-
Sakai, R.1
Stroh, J.G.2
Sullins, D.W.3
Rinehart, K.L.4
-
29
-
-
51749111836
-
-
Zhang et al. have recently reported a new cyclic thiazolyl peptide Phillipmycin containing a statine unit, whose configuration can be correctly predicted with this method. See
-
Zhang et al. have recently reported a new cyclic thiazolyl peptide Phillipmycin containing a statine unit, whose configuration can be correctly predicted with this method. See: Zhang, C.; et al. J. Am. Chem. Soc. 2008, 130, 12102-12110.
-
(2008)
J. Am. Chem. Soc
, vol.130
, pp. 12102-12110
-
-
Zhang, C.1
-
30
-
-
0035478942
-
-
Andrés, J. M, Pedrosa, R, Pérez, A, Pérez-Encabo, A. Tetrahedron 2001, 57, 8521-8530. This reference also includes two Pro-Stat derivatives in which the ABX pattern appears to be reversed. We have synthesized one of these compounds, the Pro-Stat protected as a tert-butyl ester, and find the NMR data to be consistent with the rest of our data set
-
Andrés, J. M.; Pedrosa, R.; Pérez, A.; Pérez-Encabo, A. Tetrahedron 2001, 57, 8521-8530. This reference also includes two Pro-Stat derivatives in which the ABX pattern appears to be reversed. We have synthesized one of these compounds, the Pro-Stat protected as a tert-butyl ester, and find the NMR data to be consistent with the rest of our data set.
-
-
-
-
31
-
-
0034809667
-
-
Liang, B.; Richard, D. J.; Portonovo, P. S.; Joullie, M. M. J. Am. Chem. Soc. 2001, 123, 4469-4474.
-
(2001)
J. Am. Chem. Soc
, vol.123
, pp. 4469-4474
-
-
Liang, B.1
Richard, D.J.2
Portonovo, P.S.3
Joullie, M.M.4
-
32
-
-
0026717258
-
-
Rinehart, K. L.; Sakai, R.; Kishore, V.; Sullins, D. W.; Li, K. M. J. Org. Chem. 1992, 57, 3007-3013.
-
(1992)
J. Org. Chem
, vol.57
, pp. 3007-3013
-
-
Rinehart, K.L.1
Sakai, R.2
Kishore, V.3
Sullins, D.W.4
Li, K.M.5
-
33
-
-
0002841863
-
-
Doi, T.; Kokubo, M.; Yamamoto, K.; Takahashi, T. J. Org. Chem. 1998, 63, 428-429.
-
(1998)
J. Org. Chem
, vol.63
, pp. 428-429
-
-
Doi, T.1
Kokubo, M.2
Yamamoto, K.3
Takahashi, T.4
-
34
-
-
0001201720
-
-
Palomo, C.; Miranda, J. I.; Linden, A. J. Org. Chem. 1996, 61, 9196-9201.
-
(1996)
J. Org. Chem
, vol.61
, pp. 9196-9201
-
-
Palomo, C.1
Miranda, J.I.2
Linden, A.3
-
35
-
-
32644436910
-
-
Broberg, A.; Menkis, A.; Vasiliauskas, R. J. Nat. Prod. 2006, 69, 97-102.
-
(2006)
J. Nat. Prod
, vol.69
, pp. 97-102
-
-
Broberg, A.1
Menkis, A.2
Vasiliauskas, R.3
-
36
-
-
0030592790
-
-
Okuno, T.; Ohmori, K.; Nishiyama, S.; Yamamura, S.; Nakamura, K.; Houk, K. N.; Okamoto, K. Tetrahedron 1996, 52, 14723-14734.
-
(1996)
Tetrahedron
, vol.52
, pp. 14723-14734
-
-
Okuno, T.1
Ohmori, K.2
Nishiyama, S.3
Yamamura, S.4
Nakamura, K.5
Houk, K.N.6
Okamoto, K.7
-
37
-
-
0034703342
-
-
Ishida, K, Murakami, M. J. Org. Chem. 2000, 65, 5898-5900, The vicinal coupling constants for the methylene proton signals (δH 2.35 and 2.28) in Table 1 of this reference are transposed. We thank Drs. Ishida, Murakami, and Okada for providing copies of the original 1H NMR spectrum so that we could check these data. The NMR spectra is included in our Supporting Information
-
Ishida, K.; Murakami, M. J. Org. Chem. 2000, 65, 5898-5900, The vicinal coupling constants for the methylene proton signals (δH 2.35 and 2.28) in Table 1 of this reference are transposed. We thank Drs. Ishida, Murakami, and Okada for providing copies of the original 1H NMR spectrum so that we could check these data. The NMR spectra is included in our Supporting Information.
-
-
-
-
38
-
-
10044224781
-
-
Isolation: Nakatani, S.; Kamata, K.; Sato, M.; Onuki, H.; Hirota, H.; Matsumoto, J.; Ishibashi, M. Tetrahedron Lett. 2005, 46, 267-271.
-
Isolation: Nakatani, S.; Kamata, K.; Sato, M.; Onuki, H.; Hirota, H.; Matsumoto, J.; Ishibashi, M. Tetrahedron Lett. 2005, 46, 267-271.
-
-
-
-
39
-
-
37549039089
-
-
Synthesis: Hanazawa, S.; Arai, M.; Li, X.; Ishibashi, M. Bioorg. Med. Chem. Lett. 2008, 18, 95-98.
-
Synthesis: Hanazawa, S.; Arai, M.; Li, X.; Ishibashi, M. Bioorg. Med. Chem. Lett. 2008, 18, 95-98.
-
-
-
-
40
-
-
0034715481
-
-
Isolation: Nakao, Y.; Fujita, M.; Warabi, K.; Matsunaga, S.; Fusetani, N. J. Am. Chem. Soc. 2000, 122, 10462-10463.
-
Isolation: Nakao, Y.; Fujita, M.; Warabi, K.; Matsunaga, S.; Fusetani, N. J. Am. Chem. Soc. 2000, 122, 10462-10463.
-
-
-
-
41
-
-
34547563523
-
-
Synthesis: Konno, H.; Kubo, K.; Makabe, H.; Toshiro, E.; Hinoda, N.; Nosaka, K.; Akaji, K. Tetrahedron 2007, 63, 9502-9513.
-
Synthesis: Konno, H.; Kubo, K.; Makabe, H.; Toshiro, E.; Hinoda, N.; Nosaka, K.; Akaji, K. Tetrahedron 2007, 63, 9502-9513.
-
-
-
-
42
-
-
85069133827
-
-
Occasionally, H2-2 appeared as a simple doublet in the initial proton spectra of 6-24 immediately after silica chromatography. After 24 h in CDCl3, these proton signals were generally resolved.
-
Occasionally, H2-2 appeared as a simple doublet in the initial proton spectra of 6-24 immediately after silica chromatography. After 24 h in CDCl3, these proton signals were generally resolved.
-
-
-
-
43
-
-
85069131808
-
-
Because of this requirement of CDCl3 solubility, data for the deprotected compounds 6-24 were generally not included.
-
Because of this requirement of CDCl3 solubility, data for the deprotected compounds 6-24 were generally not included.
-
-
-
-
44
-
-
0037077057
-
-
(a) Roush, W. R.; Bannister, T. D.; Wendt, M. D.; Van Nieuwenhze, M. S.; Gustin, D. J.; Dilley, G. J.; Lane, G. C.; Scheldt, K. A.; Smith, W. J., III. J. Org. Chem. 2002, 67, 4284-4289.
-
(2002)
J. Org. Chem
, vol.67
, pp. 4284-4289
-
-
Roush, W.R.1
Bannister, T.D.2
Wendt, M.D.3
Van Nieuwenhze, M.S.4
Gustin, D.J.5
Dilley, G.J.6
Lane, G.C.7
Scheldt, K.A.8
Smith III, W.J.9
-
45
-
-
28744431819
-
-
(b) Dias, L. C.; Aguilar, A. M., Jr.; Steil, L. J.; Roush, W. R. J. Org. Chem. 2005, 70, 10461-10465.
-
(2005)
J. Org. Chem
, vol.70
, pp. 10461-10465
-
-
Dias, L.C.1
Aguilar Jr., A.M.2
Steil, L.J.3
Roush, W.R.4
-
46
-
-
0020822822
-
-
Rich, D. H.; Terada, Y.; Kawai, M. Int. J. Pept. Prot. Res. 1983, 22, 325-332.
-
(1983)
Int. J. Pept. Prot. Res
, vol.22
, pp. 325-332
-
-
Rich, D.H.1
Terada, Y.2
Kawai, M.3
-
47
-
-
0000157603
-
-
(a) Stiles, M.; Winkler, R. R.; Chang, Y.-L.; Traynor, L. J. Am. Chem. Soc. 1964, 86, 3337-3342.
-
(1964)
J. Am. Chem. Soc
, vol.86
, pp. 3337-3342
-
-
Stiles, M.1
Winkler, R.R.2
Chang, Y.-L.3
Traynor, L.4
-
48
-
-
33947085164
-
-
(b) House, H. O.; Crumrine, D. S.; Teranishi, A. Y.; Olmstead, H. D. J. Am. Chem. Soc. 1973, 95, 3310-3324.
-
(1973)
J. Am. Chem. Soc
, vol.95
, pp. 3310-3324
-
-
House, H.O.1
Crumrine, D.S.2
Teranishi, A.Y.3
Olmstead, H.D.4
-
49
-
-
0023446546
-
-
Toniolo, C.; Valle, G.; Bonora, G. M.; Lelj, F.; Barone, V.; Fraternali, F.; Callet, G.; Wagnon, J.; Nisato, D. Int. J. Pept. Prot. Res. 1987, 30, 583-595.
-
(1987)
Int. J. Pept. Prot. Res
, vol.30
, pp. 583-595
-
-
Toniolo, C.1
Valle, G.2
Bonora, G.M.3
Lelj, F.4
Barone, V.5
Fraternali, F.6
Callet, G.7
Wagnon, J.8
Nisato, D.9
-
50
-
-
0035913767
-
-
Kitamura, M.; Nakano, K.; Miki, T.; Okada, M.; Noyori, R. J. Am. Chem. Soc. 2001, 123, 8939-8950.
-
(2001)
J. Am. Chem. Soc
, vol.123
, pp. 8939-8950
-
-
Kitamura, M.1
Nakano, K.2
Miki, T.3
Okada, M.4
Noyori, R.5
-
51
-
-
0015618793
-
-
Whelton, B. D.; Lowry, B. R.; Carr, J. B.; Huitric, A. C. J. Pharm. Sci. 1973, 62, 728-737.
-
(1973)
J. Pharm. Sci
, vol.62
, pp. 728-737
-
-
Whelton, B.D.1
Lowry, B.R.2
Carr, J.B.3
Huitric, A.C.4
|