Heterocycles p. 1199 - 1204 (1993)
Update date:2022-08-03
Topics:
Crich, David
Lim, Linda B.L.
5-hydroxytryptophan was converted to pyrroloindole (3), which on deprotonation with LDA and subsequent reaction with alkyl halides gave the C-2 alkylated derivatives (6-9) cleanly with retention of configuration.Reversion to the 5-hydroxytryptophan skeleton was then achieved by stirring in trifluoroacetic acid and deprotection by treatment with sodium in liquid ammonia followed by saponification.
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Doi:10.1021/jo00073a017
(1993)Doi:10.1002/chir.22193
(2013)Doi:10.1002/pca.1237
(2010)Doi:10.1021/om201010a
(2012)Doi:10.1080/15257770.2011.594031
(2011)Doi:10.1021/ma202433y
(2012)