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Synthesis 2001(11): 1639-1644
DOI: 10.1055/s-2001-16757
PAPER
© Georg Thieme Verlag Stuttgart · New York

Stereospecific Syntheses of 2-Alkyl and 2-Phenyl Substituted 3-(2,6-Dimethyl-4-hydroxyphenyl)propanoic Acids

Yixin Lu*, Peter W. Schiller*
Laboratory of Chemical Biology and Peptide Research, Clinical Research Institute of Montreal, 110 Pine Avenue West, Montreal, Quebec, Canada, H2W 1R7
Fax: +1(514)9875513; e-Mail: schillp@ircm.qc.ca;
Further Information

Publication History

Received 9 February 2001
Publication Date:
28 September 2004 (online)

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Abstract

Stereospecific syntheses of 2-methyl-, 2-ethyl-, 2-cyclohexyl- and 2-phenyl- substituted 3-(2,6-dimethyl-4-hydroxyphenyl)propanoic acids were developed. The key steps for the formation of the stereogenic centers involved the utilization of Evans" 4-benzyl-2-oxazolidinone chiral auxiliary. These compounds were designed to replace the N-terminal tyrosine residue in opioid peptides.

Key words

amino acids - tyrosine analogues - asymmetric synthesis - chiral auxiliaries - Heck reaction

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1

Present address: Research Center for Materials Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan.