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An asymmetric synthesis of l-[3-13C]phenylalanine and l-[3-13C]tyrosine from [13C]carbon monoxide

✍ Scribed by Kazuhiko Takatori; Mikiko Nishihara; Yukie Nishiyama; Masahiro Kajiwara

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
520 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis

L-[3-13C]Phenylalanine and L-[3-13C]tyrosine were synthesized. [et-13C]Benzyl bromides were prepared from [13C]carbon monoxide via the palladium-catalyzed carboaikoxylation of aryl halides. The asymmetric carbon corresponding to the 2-position in phenylalanine was introduced by the diastereoselective alkylation of Dellaria's oxazinone with [et-13C]benzyl bromides. Finally, ethanolysis, deprotection, hydrogenolysis and acid hydrolysis of the resulting alkylated oxazinones gave L-[3-13C]phenylalanine and L-[3-13C]tyrosine in high optical purity.

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