Stereochemical Studies. XV. Neighboring Aryl Group Participation in Nitrous Acid Deaminations of L-Phenylalanine and Its p-Nitro and p-Methoxy Derivatives. Conversion of L-Phenylalanine to naturally Occurring S-Tropic Acid

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概要

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• Detailed examinations of nitrous acid deaminations of L-phenylalanine (VIb) and its p-nitro (VIa) and p-methoxy (VIc) derivatives in 1 N sulfuric acid, acetic acid, and trifluoroacetic acid have shown that the reaction patterns (yields of products and their stereochemical results) differ considerably both with the solvent employed and with the substituent attached to the aromatic ring. These results were explained as due to effects of both the neighboring carboxylate group and the neighboring aryl group. Successful conversion of L-phenylalanine to naturally occurring (S)-tropic acid ((S)-VIIIb X=OH) is also described by the application of the present results.

• 公益社団法人日本薬学会の論文
• 1972-06-25

著者

• 古賀 憲司

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 山田 俊一

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• Koga Kenjiro

  Department Of Pharmaceutics Faculty Of Pharmaceutical Sciences Hokuriku University

• 呉 欽敬

  Faculty Of Pharmaceutical Sciences University Of Tokyo

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