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(a) Stoll, A.; Rutschmann, J.; Petrzilka, T. Helv. Chim. Acta 1950, 33, 2257-2261.
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(a) Teranishi, K.; Hayashi, S.; Nakatsuka, S.; Goto T. Tetrahedron Lett. 1994, 35, 8173-8176.
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Teranishi, K.1
Hayashi, S.2
Nakatsuka, S.3
Goto, T.4
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19
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4344623594
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note
-
(b) Although Goto's method has given a really short route to tetracyclic 4a and 4c, the application of the expensive and dangerous n-BuLi at -78°C can interfere with their scale-up preparation. In our modification powdered KOH was applied for deprotonation of 3 at 0°C. After acylation at room temperature, the obtained crude product was transformed directly to 4c in 43-46% overall yield.
-
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-
-
20
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0344117578
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(a) Moldvai, I.; Temesvári-Major, E.; Gács-Baitz, E.; Egyed, O.; Gömöry, A.; Nyulászi, L.; Szántay, Cs. Heterocycles 1999, 51, 2321-2333.
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Heterocycles
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Moldvai, I.1
Temesvári-Major, E.2
Gács-Baitz, E.3
Egyed, O.4
Gömöry, A.5
Nyulászi, L.6
Szántay, Cs.7
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21
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0034163799
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(b) Moldvai, I.; Temesvári-Major E.; Gács-Baitz, E.; Egyed, O.; Nyulászi L.; Szántay, Cs. Hetrocycles 2000, 53, 759.
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Hetrocycles
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Moldvai, I.1
Temesvári-Major, E.2
Gács-Baitz, E.3
Egyed, O.4
Nyulászi, L.5
Szántay, Cs.6
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22
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0037685032
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Incze, M.; Moldvai, I.; Temesvári-Major, E.; Dörnyei, G.; Kajtár-Peredy, M.; Szántay, Cs. Tetrahedron 2003, 59, 4281-4286.
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(2003)
Tetrahedron
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Incze, M.1
Moldvai, I.2
Temesvári-Major, E.3
Dörnyei, G.4
Kajtár-Peredy, M.5
Szántay, Cs.6
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23
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13044281688
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Moldvai, I.; Temesvári-Major, E.; Balázs, M.; Gács-Baitz, E.; Egyed, O.; Szántay, Cs. J. Chem. Res. (S) 1999, 687; J. Chem. Res. (M) 1999, 3018-3029.
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J. Chem. Res. (S)
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Moldvai, I.1
Temesvári-Major, E.2
Balázs, M.3
Gács-Baitz, E.4
Egyed, O.5
Szántay, Cs.6
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24
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4344650601
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Moldvai, I.; Temesvári-Major, E.; Balázs, M.; Gács-Baitz, E.; Egyed, O.; Szántay, Cs. J. Chem. Res. (S) 1999, 687; J. Chem. Res. (M) 1999, 3018-3029.
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25
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33947460292
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Kornfeld, E. C.; Fornefeld, E. J.; Kline, G. B.; Morrison, D. E.; Jones, G.; Woodward, R. B. J. Am. Chem. Soc. 1956, 78, 3087-3114.
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Kornfeld, E.C.1
Fornefeld, E.J.2
Kline, G.B.3
Morrison, D.E.4
Jones, G.5
Woodward, R.B.6
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26
-
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0015973611
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The first synthesis of racemic 7 has been performed via oxidation of the corresponding alcohol with the 2,3-dihydroindole ring. Only one characterization datum (mp 145-148°C) of (±)-7 has been described. See: Bach, N. J.; Hall, D. A.; Kornfeld, E. J. J. Med. Chem. 1974, 17, 312-314.
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J. Med. Chem.
, vol.17
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Bach, N.J.1
Hall, D.A.2
Kornfeld, E.J.3
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28
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4344665287
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In press
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(b) Moldvai, I.; Gács-Baitz, E.; Temesvári-Major, E.; Incze, M.; Poppe, L.; Szántay, Cs. Heterocycles. In press.
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Heterocycles
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Moldvai, I.1
Gács-Baitz, E.2
Temesvári-Major, E.3
Incze, M.4
Poppe, L.5
Szántay, Cs.6
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84987288476
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(a) Roth, M.; Dubs, P.; Götschi, E.; Eschenmoser, A. Helv. Chim. Acta 1971, 54, 710-734.
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Helv. Chim. Acta
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Dubs, P.2
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(b) Waldvogel, E.; Engeli, P.; Küsters, E. Helv. Chim. Acta 1997, 80, 2084-2099.
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(a) Schöllkopf, U.; Schröder, R.; Blume, E. Justus Liebigs Ann. Chem. 1972, 766, 130-141.
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, vol.766
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Schöllkopf, U.1
Schröder, R.2
Blume, E.3
-
35
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0033534430
-
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It is worth mentioning that Rapoport and co-workers published a method for synthesizing an advanced intermediate of the Ergot alkaloids, an optically active amino derivative of Uhle's ketone, following an entirely different route. Hurt, C. R.; Lin, R.; Rapoport, H. J. Org. Chem. 1999, 64, 225-233.
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J. Org. Chem.
, vol.64
, pp. 225-233
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Hurt, C.R.1
Lin, R.2
Rapoport, H.3
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36
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0014457059
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Stadler, P. A.; Guttmann, S.; Hauth, H.; Huguenin, R. L.; Sandrin, E.; Wersin, G.; Willems, H.; Hofmann, A. Helv. Chim. Acta 1969, 52, 1549-1564.
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Helv. Chim. Acta
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Stadler, P.A.1
Guttmann, S.2
Hauth, H.3
Huguenin, R.L.4
Sandrin, E.5
Wersin, G.6
Willems, H.7
Hofmann, A.8
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37
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4344626647
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Kollonitsch, J.; Hajós, A.; Kraut, M.; Gábor V. Acta Chim. Hung. 1955, 6, 381-395; Chem. Abstr. 1955, 49, 6872h.
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Acta Chim. Hung.
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Kollonitsch, J.1
Hajós, A.2
Kraut, M.3
Gábor, V.4
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38
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4344696328
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Kollonitsch, J.; Hajós, A.; Kraut, M.; Gábor V. Acta Chim. Hung. 1955, 6, 381-395; Chem. Abstr. 1955, 49, 6872h.
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Chem. Abstr.
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39
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4344642411
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Hungarian patent 156.385, 1969
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Magó-Karácsony, E.; Balogh, T.; Borsi, J.; Elek, S.; Polgari, I.; Löwinger, L. Hungarian patent 156.385, 1969; Chem. Abstr. 1970, 72, 32105r.
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Magó-Karácsony, E.1
Balogh, T.2
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Elek, S.4
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Löwinger, L.6
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41
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4344613109
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Bandula, R.; Vasilesu, M. Rev. Roum. Chim. 1995, 40, 1189-1195; Chem. Abstr. 1996, 125, 114925k.
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Rev. Roum. Chim.
, vol.40
, pp. 1189-1195
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Bandula, R.1
Vasilesu, M.2
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4344636487
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Bandula, R.; Vasilesu, M. Rev. Roum. Chim. 1995, 40, 1189-1195; Chem. Abstr. 1996, 125, 114925k.
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(1996)
Chem. Abstr.
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-
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44
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4344633979
-
-
note
-
The formation of ring D was confirmed by the presence of an NOE effect between H-9 and H-12 protons. The chemical shifts of C-9 and C-10 carbons (118.8 and 156.0 ppm, respectively) are also characteristic for an α,β-unsaturated ketone unit.
-
-
-
-
45
-
-
4344593481
-
-
note
-
β proton (3.37 ppm) leads to observation of an NOE at the formyl proton (8.09 ppm), while the tosyl protons gave NOE with H-9 (7.88 ppm).
-
-
-
-
46
-
-
4344646900
-
-
note
-
β protons.
-
-
-
-
47
-
-
4344615084
-
-
note
-
β (3.0 and 3.4 Hz, respectively).
-
-
-
-
48
-
-
4344682305
-
-
note
-
β protons (10.5 Hz).
-
-
-
-
51
-
-
4344582584
-
-
note
-
β protons.
-
-
-
-
52
-
-
4344710976
-
-
note
-
6 solution 2a experienced a rapid C-8 epimerization and as a result 2b appeared in the isomer mixture.
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-
-
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