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16
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The facile conversion of the lactamol into the enamine was surprising, considering that other less substituted lactamols were converted into the corresponding enamine only upon heating to 160 °C in HMPA for several hours: Dieter, R. K.; Sharma, R. R. J. Org. Chem. 1996, 61, 4180-4184.
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17
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0012190166
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note
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The synthesis of 17 commences with 6-methoxyisatine which is commercially available, see Supporting Information.
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-
-
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18
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0012108219
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note
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β at C-14.
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19
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0012108528
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Saxon, J. E., Ed.; Wiley-Interscience: New York
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20
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0012108220
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1H NMR, see Supporting Information.
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21
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0032575230
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22
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0012187623
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Although we did not anticipate stereoselectivity in this condensation reaction of the simple tryptamine derivative, it is important to note that stereoselective Pictet Spengler reactions have been documented employing tryptophan derivatives. Application of such methods at this stage would likely provide the desired product stereoselectively. Watson, W. H.; Krawiec, M. J.; Cox, E. D.; Hamaker, L. K.; Li, J.; Yu, P.; Czerwinski, K. M.; Deng, L.; Bennet, D. W.; Cook, J. M. J. Org. Chem. 1997, 62, 44-61.
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23
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