-
1
-
-
0342432532
-
-
note
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Abbreviations: Ala = Alanine, EDC = 1-ethyl-3-(3-(diethylamino)-propyl)carbodiimide·HCl, Fmoc = (9H-fluoren-9-ylmethoxy)carbonyl, Gly = glycine, Phe = phenylalanine, PyBrOP = bromo-tris-pyrrolidinophosphonium hexafluorophosphate, Trp = tryptophan, Val = valine.
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-
-
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2
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0032413665
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-
For recent reviews, see (a) Michael, J. P. Nat. Prod. Rep. 1998, 15, 595-606. (b) Johne, S. In Rodd's Chemistry of Carbon Compounds (Supplements to the 2nd edition); Ansell, M. F., Ed.; Elsevier: Amsterdam, 1995; Vol. IV I/J, pp 223-240.
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Nat. Prod. Rep.
, vol.15
, pp. 595-606
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Michael, J.P.1
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3
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0032413665
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Ansell, M. F., Ed.; Elsevier: Amsterdam
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For recent reviews, see (a) Michael, J. P. Nat. Prod. Rep. 1998, 15, 595-606. (b) Johne, S. In Rodd's Chemistry of Carbon Compounds (Supplements to the 2nd edition); Ansell, M. F., Ed.; Elsevier: Amsterdam, 1995; Vol. IV I/J, pp 223-240.
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(1995)
Rodd's Chemistry of Carbon Compounds (Supplements to the 2nd Edition)
, vol.4 I-J
, pp. 223-240
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Johne, S.1
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4
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0002997751
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Penn, J.; Mantle, P. G.; Bilton, J. N.; Sheppard, R. N. J. Chem. Soc., Perkin Trans 1 1992, 1495-1496.
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J. Chem. Soc., Perkin Trans 1
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Penn, J.1
Mantle, P.G.2
Bilton, J.N.3
Sheppard, R.N.4
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5
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0026603564
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(a) Numata, A.; Takahashi, C.; Matsushita, T.; Miyamoto, T.; Kawai, K.; Usami, Y.; Matsumura, E.; Inoue, M.; Ohishi, H.; Shingu, T. Tetrahedron Lett. 1992, 33, 1621-1624.
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(1992)
Tetrahedron Lett.
, vol.33
, pp. 1621-1624
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Numata, A.1
Takahashi, C.2
Matsushita, T.3
Miyamoto, T.4
Kawai, K.5
Usami, Y.6
Matsumura, E.7
Inoue, M.8
Ohishi, H.9
Shingu, T.10
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6
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37049085124
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(b) Takahashi, C.; Matsushita, T.; Doi, M.; Minoura, K.; Shingu, T.; Kumeda, Y.; Numata, A. J. Chem. Soc., Perkin Trans, 1 1995, 2345-2353.
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J. Chem. Soc., Perkin Trans, 1
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Takahashi, C.1
Matsushita, T.2
Doi, M.3
Minoura, K.4
Shingu, T.5
Kumeda, Y.6
Numata, A.7
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7
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0027233895
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(a) Wong, S.-M.; Musza, L. L.; Kydd, G. C.; Kullnig, R.; Gillum, A. M.; Cooper, R. J. Antibiot. 1993, 46, 545-553.
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J. Antibiot.
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Wong, S.-M.1
Musza, L.L.2
Kydd, G.C.3
Kullnig, R.4
Gillum, A.M.5
Cooper, R.6
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8
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0029807874
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(b) Fujimoto, H.; Negishi, E.; Yamaguchi, K.; Nishi, N.; Yamazaki, M. Chem. Pharm. Bull. 1996, 44, 1843-1848.
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Chem. Pharm. Bull.
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Fujimoto, H.1
Negishi, E.2
Yamaguchi, K.3
Nishi, N.4
Yamazaki, M.5
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13
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0343302077
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note
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In our initial studies, we used the cheaper L-amino acids, leading to the total synthesis of ent-fumiquinazoline G, which is summarized in the Experimental Section.
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14
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0029128552
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(a) Boojamra, C. G.; Burow, K. M.; Ellman, J. A. J. Org. Chem. 1995, 60, 5742-5743.
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J. Org. Chem.
, vol.60
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Boojamra, C.G.1
Burow, K.M.2
Ellman, J.A.3
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15
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0030932342
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(b) Boojamra, C. G.; Burow, K. M.; Thompson, L. A.; Ellman, J. A. J. Org. Chem. 1997, 62, 1240-1256.
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J. Org. Chem.
, vol.62
, pp. 1240-1256
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Boojamra, C.G.1
Burow, K.M.2
Thompson, L.A.3
Ellman, J.A.4
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16
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0343737607
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note
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Alternatively, tryptophan methyl ester was refluxed with isatoic anhydride in 1,2-dichloroethane to give 8 in 93% yield.
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17
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33845375891
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Carpino, L. A.; Cohen, B. J.; Stephens, K. E., Jr.; Sadat-Aalaee, S. Y.; Tien, J.-H.; Langridge, D. C. J. Org. Chem. 1986, 51, 3732-3734.
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(1986)
J. Org. Chem.
, vol.51
, pp. 3732-3734
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Carpino, L.A.1
Cohen, B.J.2
Stephens K.E., Jr.3
Sadat-Aalaee, S.Y.4
Tien, J.-H.5
Langridge, D.C.6
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18
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0018611071
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-
For example, see: (a) Büchi, G.; DeShong, P. R.; Katsumura, S.; Sugimura, Y. J. Am. Chem. Soc. 1979, 101, 5084-5086. (b) Ohnuma, T.; Kimura, Y.; Ban, Y. Tetrahedron Lett. 1981, 22, 4969- 4972. (c) Nakagawa, M.; Taniguchi, M.; Sodeoka, M.; Ito, M.; Yamaguchi, K.; Hino, T. J. Am. Chem. Soc. 1983, 105, 3709-3710.
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(1979)
J. Am. Chem. Soc.
, vol.101
, pp. 5084-5086
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-
Büchi, G.1
DeShong, P.R.2
Katsumura, S.3
Sugimura, Y.4
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19
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0008204719
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For example, see: (a) Büchi, G.; DeShong, P. R.; Katsumura, S.; Sugimura, Y. J. Am. Chem. Soc. 1979, 101, 5084-5086. (b) Ohnuma, T.; Kimura, Y.; Ban, Y. Tetrahedron Lett. 1981, 22, 4969-4972. (c) Nakagawa, M.; Taniguchi, M.; Sodeoka, M.; Ito, M.; Yamaguchi, K.; Hino, T. J. Am. Chem. Soc. 1983, 105, 3709-3710.
-
(1981)
Tetrahedron Lett.
, vol.22
, pp. 4969-4972
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-
Ohnuma, T.1
Kimura, Y.2
Ban, Y.3
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20
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0021060317
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For example, see: (a) Büchi, G.; DeShong, P. R.; Katsumura, S.; Sugimura, Y. J. Am. Chem. Soc. 1979, 101, 5084-5086. (b) Ohnuma, T.; Kimura, Y.; Ban, Y. Tetrahedron Lett. 1981, 22, 4969- 4972. (c) Nakagawa, M.; Taniguchi, M.; Sodeoka, M.; Ito, M.; Yamaguchi, K.; Hino, T. J. Am. Chem. Soc. 1983, 105, 3709-3710.
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(1983)
J. Am. Chem. Soc.
, vol.105
, pp. 3709-3710
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-
Nakagawa, M.1
Taniguchi, M.2
Sodeoka, M.3
Ito, M.4
Yamaguchi, K.5
Hino, T.6
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21
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0342866986
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note
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He and Snider (ref 8) were unsuccessful with such reactions on a similar peptide, although details are not given.
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23
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0342866982
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note
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We did not observe any enantiomer by NMR analysis with chiral lanthanide shift reagents (detection limit of 2% from control experiments).
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29
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0343302058
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note
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Although we use a neutral solvent, it is possible that the reaction is catalyzed by the piperidine byproduct released.
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30
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0343302059
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note
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The absolute configuration of the natural product was not assigned, and we were unable to obtain a sample.
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31
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0343737590
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note
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For both fumiquinazoline F and fiscalin B, the melting point and optical rotation for our synthetic material is significantly higher than reported for the natural product, probably reflecting the difficulty of purifying the limited amount isolated and obtaining accurate measurements.
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32
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0342432509
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note
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2.
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33
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0032350681
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Rauter, A. P.; Fernandes, A. C.; Figueiredo, J. A. J. Carbohydr. Chem. 1998, 17, 1037-1045.
-
(1998)
J. Carbohydr. Chem.
, vol.17
, pp. 1037-1045
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Rauter, A.P.1
Fernandes, A.C.2
Figueiredo, J.A.3
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34
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0032481011
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For our successful synthesis of luotonin A by another approach, see: Wang, H.; Ganesan, A. Tetrahedron Lett. 1998, 39, 9097-9098.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 9097-9098
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Wang, H.1
Ganesan, A.2
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