-
1
-
-
0011768892
-
-
accepted
-
1. Synthetic Studies on Indole and Related Compounds. Part 42. Part 41 : "A General Synthetic Route for 1-Substituted 4-Oxygenated β-Carbolines" Suzuki, H; Iwata(nee Miyagi), C; Sakurai, K.; Tokumoto, K.; Takahashi, H.; Hanada, M; Yokoyama, Y.; Murakami, Y. Tetrahedron, accepted.
-
Tetrahedron
-
-
Suzuki, H.1
Iwata, C.2
Sakurai, K.3
Tokumoto, K.4
Takahashi, H.5
Hanada, M.6
Yokoyama, Y.7
Murakami, Y.8
-
3
-
-
0021403686
-
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3 . a) Rebeck, J. Jr.; Tai, D. F.; Shue, Y.-K.J. Am. Chem. Soc., 1984, 106, 1813-1819.
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Rebeck J., Jr.1
Tai, D.F.2
Shue, Y.-K.3
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4
-
-
0025150557
-
-
b) Kogan, T. P.; Somers, T. C.; Vemuti, M. C. Tetrahedron, 1990, 46, 6623-6632.
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Tetrahedron
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Kogan, T.P.1
Somers, T.C.2
Vemuti, M.C.3
-
6
-
-
37049070292
-
-
d) Mascal, M.; Moody, C. J.; Slawin, A. M. Z.; Williams, D. J. J. Chem. Soc., Perkin Trans. I, 1992, 823-830.
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J. Chem. Soc., Perkin Trans. I
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-
Mascal, M.1
Moody, C.J.2
Slawin, A.M.Z.3
Williams, D.J.4
-
7
-
-
0027279339
-
-
e) Sommelhack, M. F.; Knochel, P.; Singleton, T. Tetrahedron Lett., 1993, 32, 5051-5054.
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(1993)
Tetrahedron Lett.
, vol.32
, pp. 5051-5054
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-
Sommelhack, M.F.1
Knochel, P.2
Singleton, T.3
-
8
-
-
0000555181
-
-
4 . a) Yokoyama, Y.; Takahashi, M.; Kohno, Y.; Kataoka, K.; Fujikawa, Y.; Murakami, Y. Heterocycles 1990, 31, 803-804.
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(1990)
Heterocycles
, vol.31
, pp. 803-804
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-
Yokoyama, Y.1
Takahashi, M.2
Kohno, Y.3
Kataoka, K.4
Fujikawa, Y.5
Murakami, Y.6
-
9
-
-
0000490122
-
-
b) Yokoyama, Y.; Takahashi, M.; Higaki, C.; Shidori, K.; Moriguti, M.; Ando, C.; Murakami, M. Heterocycles, 1993, 36, 1739-1742.
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(1993)
Heterocycles
, vol.36
, pp. 1739-1742
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-
Yokoyama, Y.1
Takahashi, M.2
Higaki, C.3
Shidori, K.4
Moriguti, M.5
Ando, C.6
Murakami, M.7
-
10
-
-
0028331279
-
-
c) Yokoyama, Y.; Takahashi, M.; Takashima, M.; Kohno, Y; Kobayashi, H.; Kataoka, K.; Shidori, K.; Murakami, Y. Chem. Pharm. Bull. 1994, 42, 832-838.
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Chem. Pharm. Bull.
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-
Yokoyama, Y.1
Takahashi, M.2
Takashima, M.3
Kohno, Y.4
Kobayashi, H.5
Kataoka, K.6
Shidori, K.7
Murakami, Y.8
-
11
-
-
0028931481
-
-
5 . Yokoyama, Y.; Matsumoto, T.; Murakami, Y.J. Org. Chem., 1995, 60, 1486-1487.
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(1995)
J. Org. Chem.
, vol.60
, pp. 1486-1487
-
-
Yokoyama, Y.1
Matsumoto, T.2
Murakami, Y.3
-
15
-
-
0001508464
-
-
d) Oppolzer, W.; Grayson, J. I.; Wegmann, H.; Urrea, M. Tetrahedron, 1983, 39, 3695-3705.
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(1983)
Tetrahedron
, vol.39
, pp. 3695-3705
-
-
Oppolzer, W.1
Grayson, J.I.2
Wegmann, H.3
Urrea, M.4
-
16
-
-
85008106365
-
-
e) Somei, M.; Makita, Y.; Yamada, F. Chem. Pharm. Bull., 1986, 34, 948-950. Total synthesis of optically active (-)-8 : Kardos, N.; Genet, J.-P. Tetrahedron Asymmetry, 1994, 5, 1525-1533.
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(1986)
Chem. Pharm. Bull.
, vol.34
, pp. 948-950
-
-
Somei, M.1
Makita, Y.2
Yamada, F.3
-
17
-
-
0028146150
-
-
e) Somei, M.; Makita, Y.; Yamada, F. Chem. Pharm. Bull., 1986, 34, 948-950. Total synthesis of optically active (-)-8 : Kardos, N.; Genet, J.-P. Tetrahedron Asymmetry, 1994, 5, 1525-1533.
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(1994)
Tetrahedron Asymmetry
, vol.5
, pp. 1525-1533
-
-
Kardos, N.1
Genet, J.-P.2
-
18
-
-
0011710835
-
-
note
-
7. The R configuration of 3, the opposite configuration to natural tryptophan, has to be used to obtain the same stereoisomer as natural product.
-
-
-
-
19
-
-
0011750170
-
-
note
-
5, and the optical purity was determined as 55% ee. by HPLC using a chiral column (Daicel Chiralcel OD, Hexane : EtOH = 50 : 1).
-
-
-
-
20
-
-
0011750171
-
-
note
-
9. The observation of NOE between vinylic proton at 6.73ppm and aromatic proton at 7.64ppm shows that the olefin geometry is Z-configuration.
-
-
-
-
23
-
-
0011711590
-
-
note
-
2NH = 200 : 1 : 0.3 for 17). This means that the conversion step (10 → 6) and cyclization step (6 → 7) did not cause racemization.
-
-
-
-
25
-
-
84984085861
-
-
D=-240° (pyridine), mp 222 °C : Stauffacher, D.; Tscherter, H. Helv. Chemica Acta, 1964, 47, 2186-2194.
-
(1964)
Helv. Chemica Acta
, vol.47
, pp. 2186-2194
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-
Stauffacher, D.1
Tscherter, H.2
-
26
-
-
0027933793
-
-
15. Hornwell, D. C.; Nichols, P. D.; Ratcliffe, G. S.; Roberts, E.J. Org. Chem., 1994, 59, 4418-4423.
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(1994)
J. Org. Chem.
, vol.59
, pp. 4418-4423
-
-
Hornwell, D.C.1
Nichols, P.D.2
Ratcliffe, G.S.3
Roberts, E.4
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