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Synthsis of meleylacetoacetate‐2 14 C, maleylacetone‐1 14 C and homogentisic acid γ‐lactone‐α‐ 14 C. 1
Author(s) -
Seltzer S.
Publication year - 1973
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590090406
Subject(s) - homogentisic acid , lactone , chemistry , decarboxylation , isomerization , hydrolysis , stereochemistry , medicinal chemistry , organic chemistry , catalysis , biochemistry
Syntheses of the title compounds were accomplished by a sequence of reactions involving Friedel Crafts 14 C‐acetylation of p‐dimethoxybenze, willgerodt rearrangement of 2, 5‐dimethoxyacetophenone‐carbonyl‐ 14 C (I) to 2, 5‐dimethoxyphenylactic acid‐a 14 C (II), followed by hydrolysis to homogentisic acid γ‐lactone‐α‐ 14 C(III). Oxygenation of the lactone by an osygenaser from animal liver provided a solution of maleyacetoacetate‐2‐ 14 C (IV). Decarboxylation of this matrial leads to a solution of maleylacetone‐1‐ 14 C (V). Funaruylactone‐1‐ 14 C (VT) can be obtained from V by silver ion‐catalysed cis‐trans isomerization.