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A Novel General Route for the Synthesis of C‐Glycosyl Tyrosine Analogues
Author(s) -
Brenna Elisabetta,
Fuganti Claudio,
Grasselli Piero,
Serra Stefano,
Zambotti Sabrina
Publication year - 2002
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20020415)8:8<1872::aid-chem1872>3.0.co;2-a
Subject(s) - glycosyl , tyrosine , ring (chemistry) , chemistry , stereochemistry , amino acid , function (biology) , combinatorial chemistry , organic chemistry , biochemistry , biology , evolutionary biology
A general method for the synthesis of C‐glycosyl amino acids is described here. The stereoisomerically pure tyrosine analogues α ‐ L ‐ 4 and β ‐ L ‐ 6 are prepared in reasonable overall yields from allyl derivatives 10 and 11 . The key step is a benzannulation procedure which is employed in the creation of the aromatic ring that bears the amino acid function.