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

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

References

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1

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