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For an earlier communication of this synthesis, see: Edmondson, S. D.; Danishefsky, S. J. Angew. Chem., Int. Ed. 1998, 37, 1138.
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10
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0001048369
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The Pictet-Spengler reaction of 8 and 38 with 10 has been reported: (a) Harrison, D. M.; Sharma, R. B. Tetrahedron Lett. 1986, 27, 521. (b) Kodato, S.; Nakagawa, M.; Hongu, M.; Kawate, T.; Hino, T. Tetrahedron 1988, 44, 359.
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11
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0023850429
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The Pictet-Spengler reaction of 8 and 38 with 10 has been reported: (a) Harrison, D. M.; Sharma, R. B. Tetrahedron Lett. 1986, 27, 521. (b) Kodato, S.; Nakagawa, M.; Hongu, M.; Kawate, T.; Hino, T. Tetrahedron 1988, 44, 359.
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Kawate, T.4
Hino, T.5
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12
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0031013399
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For lead references of the Pictet-Spengler reaction to synthesize cis and trans tetrahydrocarbolines, see: (a) Cox, E. D.; Hamaker, L. K.; Li, J.; Yu, P.; Czerwinski, K. M.; Deng., L.; Bennett, D. W.; Cook, J. M.; Watson, W. H.; Krawlec, M. J. Org. Chem. 1997, 62, 44. (b) Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797.
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Krawlec, M.10
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13
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4243241249
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For lead references of the Pictet-Spengler reaction to synthesize cis and trans tetrahydrocarbolines, see: (a) Cox, E. D.; Hamaker, L. K.; Li, J.; Yu, P.; Czerwinski, K. M.; Deng., L.; Bennett, D. W.; Cook, J. M.; Watson, W. H.; Krawlec, M. J. Org. Chem. 1997, 62, 44. (b) Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797.
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15
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18
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(a) Takayama, H.; Masubuchi, K.; Kitajima, M.; Aimi, N.; Sakai, S.-i. Tetrahedron 1989, 45, 1327.
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19
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23
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13044299349
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note
-
2; then TBSCl, imid, DMF. Attempts to oxidatively rearrange this molecule resulted in complicated mixtures and loss of silicon.
-
-
-
-
24
-
-
13044315413
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-
note
-
An observation of molecular models reveals that the corresponding trans ring fusion, resulting from attack of water on the α-face of 21, would be a highly strained molecule and, thus, less likely to form.
-
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-
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25
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0028019446
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(a) Pelligrini, C.; Strassler, C.; Weber, M.; Borschberg, H.-J. Tetrahedron: Asymmetry 1994, 5, 1979.
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-
27
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13044314603
-
-
note
-
In part, the difficulty in oxidizing of 30 is due to the poor solubility of this molecule in organic solvents. Advantage was taken in the model system (Scheme 7) of the more desirable solubility properties that these molecules possess prior to diketopiperazine formation.
-
-
-
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28
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13044298733
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note
-
Spectral data of naturally occurring 1 were kindly provided by Professor Osada.
-
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29
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33745693816
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33847086491
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31
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85082554095
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85008070422
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