A short synthesis of 9-fluoroellipticine from 5-fluoroindole?
A synthesis of 9-fluoroellipticine (1c) from 5-fluoroindole (6) is described that features the regioselective lithiation of 5-fluoro-1-(phenylsulfonyl)indole (7) followed by chemoselective acylation of 3,4-pyridinedicarboxylic anhydride. Subsequent cyclization of keto acid 9 to keto lactam 10 with acetic anhydride and sequential treatment of 10 with methyllithium and sodium borohydride affords 9-fluoroellipticine.
Davis, Deborah A.,Gribble, Gordon W.
p. 422 - 430
(2019/07/31)
Novel tryptophan dioxygenase inhibitors and combined tryptophan dioxygenase/5-HT reuptake inhibitors
Tryptophan dioxygenase (TDO) is a liver enzyme that is responsible for the majority of the metabolism of tryptophan. A series of novel 3-(2-pyridylethenyl)indoles are shown to be potent inhibitors of TDO with selected members of the series also having 5-hydroxy tryptamine (5-HT) reuptake inhibitory activity. These compounds are shown to provide significant increases in the levels of tryptophan and 5-HT in the cerebrospinal fluid and are thus of interest for antidepressant therapy.
Madge,Hazelwood,Iyer,Jones,Salter
p. 857 - 860
(2007/10/03)
Intermediates for indoles
Ortho-nitrotoluenes are condensed with formamide acetals to yield the corresponding otho-nitro-β-aminestyrenes which undergo cyclization upon reduction to yield indoles.
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(2008/06/13)
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