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Current Radiopharmaceuticals

Volume 1 Issue 2
ISSN: 1874-4710
eISSN: 1874-4729

 

   All Titles

  Asymmetric Synthesis of L-[3-13C]Tryptophan
  pp.122-124 (3) Authors: Kazuhiko Takatori, Myonghui Lee, Masahiro Kajiwara
doi: 10.2174/1874471010801020122
 
 
      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).

 
  Keywords: L-[3-13C]tryptophan, labeled amino acid, chiral glycine equivalent, oxazinone
  Affiliation: Department of Medicinal Chemistry, Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose-shi, Tokyo 204-8588, Japan.
 
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