Asymmetric Synthesis of L-[3-13C]Tryptophan

Publisher: Bentham Science Publishers

E-ISSN: 1874-4729|1|2|122-124

ISSN: 1874-4710

Source: Current Radiopharmaceuticals, Vol.1, Iss.2, 2008-05, pp. : 122-124

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Abstract

Synthesis of L-[3-13C]tryptophan (2) from N,N-dimethyl[13C]formamide (4) and Dellaria's oxazinone 1 as a chiral glycine equivalent was achieved. Vilsmeier reaction of indole (5) and N,N-dimethyl[13C]formamide (4) afforded a good yield of indole-3-[13C]carbaldehyde (3), which was converted to the bromide 8. Diastereoselective alkylation of the enolate of 1 with the bromide 8 proceeded with high diastereoselectivity to give 9. Ethanolysis, hydrogenolysis and hydrolysis of 9 gave L-[3-13C]tryptophan (2).

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