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

被引：5

作者：

Takatori, Kazuhiko ^{[1
]}

Lee, Myonghui ^{[1
]}

Kajiwara, Masahiro ^{[1
]}

机构：

[1] Meiji Pharmaceut Univ, Dept Med Chem, 2-522-1 Noshio, Kiyose, Tokyo 2048588, Japan

来源：

CURRENT RADIOPHARMACEUTICALS | 2008年 / 1卷 / 02期

关键词：

L-[3-C-13] tryptophan; labeled amino acid; chiral glycine equivalent; oxazinone;

D O I：

10.2174/1874471010801020122

中图分类号：

R9 [药学];

学科分类号：

1007 ;

摘要：

Synthesis of L-[3-C-13] tryptophan (2) from N,N-dimethyl[C-13] formamide (4) and Dellaria's oxazinone 1 as a chiral glycine equivalent was achieved. Vilsmeier reaction of indole (5) and N,N-dimethyl[C-13] formamide (4) afforded a good yield of indole-3-[C-13] 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-C-13] tryptophan (2).

引用

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页码：122 / 124

页数：3

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